Novel oligosaccharides, intermediates for the manufacture of such oligosaccharides, and methods for their manufacture.

Abstract

The objective of this invention is to provide a novel oligosaccharide that can be used to manufacture a bibranched polysaccharide having an α2,6-sialic acid structure at a non-reducing end, a method for manufacturing the same, a manufacturing intermediate thereof, a method for manufacturing the same intermediate, and a method for manufacturing the same, as well as a method for manufacturing the same, the same intermediate thereof. This invention provides the novel oligosaccharide represented by the following formulas A-13 and D-13, a method for manufacturing the oligosaccharide represented by formulas A-13 and D-13 as shown in Figures 1 and 3, and a method for manufacturing the same, the same intermediate thereof.

Description

Novel oligosaccharides, intermediates for the manufacture of such oligosaccharides, and methods for their manufacture. This invention relates to a novel oligosaccharide as a bibranched polysaccharide having an α2,6-sialic acid structure at a non-reducing end, a method for manufacturing the oligosaccharide, and a method for manufacturing its intermediates and intermediates thereof. It is known that protein glycosylation has a significant impact on protein function and structure. Among these, N-binding glycans have been reported to be closely related to the physiological activity of proteins, especially bibranched N-glycans with α2,6-sialic acid structures at their non-reducing ends, which are considered the optimal structures for enhancing antibody-dependent cytotoxicity (ADCC) and complement-dependent cytotoxicity (CDC) activities (Non-Patent Literature 1). In the development and commercialization of pharmaceuticals utilizing glycans, the aim is to stably and massively manufacture high-purity glycans at an industrially viable price. To date, the reported synthesis of α2,6-sialic acid glycans can be broadly categorized into two methods: 1) a semi-chemical synthesis method combining the separation and purification of natural extracts with the chemical synthesis and enzymatic chemical conversion of the main backbone precursor; and 2) a purely chemical synthesis method. For example, as a semi-chemical synthesis method, there are reports of obtaining N-bound glycans from egg yolks by combining enzymatic and chemical methods (Non-Patent Document 2). Compared to pure chemical synthesis, these methods can synthesize the target glycans with fewer steps. On the other hand, in most cases, large quantities of egg yolks are required, and special techniques and purification equipment are needed for subsequent isolation purification from the egg yolks and purification of water-soluble unprotected glycans after chemical transformation (Patent Documents 1-4). On the other hand, the following are reported examples of pure chemical synthesis methods for α2,6-sialic acid glycan chains: (1) Total synthesis of complex 11-glycosaminoglycans having an α2,6-sialic acid site (Non-Patent Document 3) (2) Total synthesis of immunoglobulin G13 glycopeptide having an α2,6-sialic acid site (Non-Patent Document 4) (3) Total synthesis of α2,6-sialic acid 12-glycosaminoglycan N-binding glycan chain containing a core fucose (Non-Patent Document 5) (4) Total synthesis of 3-fluorinated α2,6-sialic acid 10-glycosaminoglycan chain (Non-Patent Document 6) (5) Total synthesis of asymmetric deuterated α2,6-sialic acid bibranched 11-glycosaminoglycan chains and tetrabranched 17-glycosaminoglycan chains (Non-Patent Document 7) Regarding the pure chemical synthesis of sugar chains, it is believed that with a stable manufacturing method established, they can be derived from monosaccharides in the same way as ordinary low-molecular-weight compounds, offering a high degree of freedom in the quantity produced. Furthermore, for the conversion of sugars modified with protecting groups, most purification operations involve the treatment of water-insoluble compounds, thus significantly reducing the complexity and number of steps compared to semi-chemical synthesis methods. By applying the further established chemical synthesis techniques, a variety of non-natural sugar chains can be easily synthesized. On the other hand, in the past reports mentioned above, the major synthetic challenges can be summarized in the following two points: 1) Low selectivity and low yield steps exist in the conversion and linkage of sugar fractions, which are highly difficult to construct, such as the β-mannoside fraction and the α-salivary fraction; 2) Silicone column chromatography, which is not suitable for large-scale production, is frequently used in each step of the sugar fraction conversion and linkage steps, and precise chromatographic separation and purification operations are required in multiple steps to remove byproduct isomers and impurities generated in the reaction. As mentioned above, while pure chemical synthesis of glycans has potential advantages over semi-chemical synthesis in terms of large-scale synthesis, it is difficult to say that the technology has been fully developed in terms of yield, selectivity, efficiency, and cost, and there are very few examples of it being adopted as a large-scale synthesis method. Furthermore, regarding bibranched glycans (α2,6-sialic acid glycans) with different glycan units linked at the 3 and 6 positions of mannose at the branch point, structurally, it is difficult to synthesize these bibranched glycans (α2,6-sialic acid glycans) in large quantities through natural extract induction, semi-chemical synthesis, or all-chemical synthesis. Furthermore, sugar derivatives protected by phthalimide groups sometimes require the simultaneous benzylation of multiple hydroxyl groups. In such cases, the reaction needs to proceed while suppressing the ring-opening of the phthalimide group. However, the phthalimide group readily undergoes ring-opening under strongly alkaline conditions due to the presence of trace amounts of hydroxide ions. Therefore, under the NaH / DMAc conditions used in previous benzylation reactions, the yield varies significantly depending on the amount of sodium hydroxide in the NaH. Moreover, NaH / DMAc is not suitable for large-scale synthesis due to its hazard of mixing and explosion concerns. Therefore, a method is needed to simultaneously benzylate multiple hydroxyl groups under milder conditions while suppressing the ring-opening of the phthalimide group. Furthermore, sugar derivatives protected by phthalimide groups sometimes require deacetylation. However, when trace amounts of moisture are present in the system, phthalimide readily undergoes ring-opening under alkaline conditions, necessitating strict control of the moisture content. Even moisture levels at the ppm level are insufficient to completely suppress ring-opening. Therefore, a method is needed that can simultaneously suppress the ring-opening of phthalimide groups and achieve high-yield deacetylation. Furthermore, in the chemical synthesis of oligosaccharide chains containing hydroxyl groups (which can be multiple), it is necessary to rationally utilize the selective protection and deprotection techniques of these hydroxyl groups in order to efficiently obtain the target compound. In particular, 2-naphthylmethyl has been widely used as a general protecting group for hydroxyl groups. On the other hand, as a deprotection method for 2-naphthylmethyl, a method using 2,3-dichloro-5,6-dicyano-p-benzoquinone in dichloromethane-water is known. This method provides the target deprotected form in moderate to high yields on a wide range of matrices. However, dichloromethane is generally immiscible with water, and 2,3-dichloro-5,6-dicyano-p-benzoquinone and its byproduct 2,3-dichloro-5,6-dicyano-p-dihydroxybenzoquinone are almost insoluble in dichloromethane-water, thus affecting the stirring properties. Therefore, this presents a problem when applied to large-scale synthesis. Moreover, it has been reported that, depending on the matrix used, the target deprotected form may not always be obtained in sufficient yield (Non-Patent Literature 8). Furthermore, the reaction yield tends to decrease due to the increase in benzyl groups in the matrix (Non-Patent Document 9), thus it is desirable to develop a milder and more efficient method applicable to complex matrices. As a method to achieve this objective, there are reports of improved conditions using β-pinene as an additive (Non-Patent Document 10), but even with this method, the yield remains moderate for complex matrices with multiple benzyl groups (Non-Patent Document 11). Based on the background described above, it is desirable to develop a deprotection reaction for 2-naphthylmethyl groups under milder conditions, yielding the deprotected form in high yield. Furthermore, liquid-phase synthesis and solid-phase synthesis are known chemical synthesis methods for oligosaccharide chains. Liquid-phase synthesis is easier to track reactions and scale up because it uses conventional organic synthesis techniques, but it is time-consuming and labor-intensive due to the need for step-by-step post-processing and purification. Solid-phase synthesis can be automated, which is advantageous for rapid production, but its scale-up is limited by equipment limitations. Also, due to its lower reactivity, it requires excessive use of sugar donors used in sugar extension reactions, making it unsuitable for large-scale industrial synthesis. Furthermore, it is difficult to confirm the progress of the reaction at intermediate stages (Patent Document 5). To address these issues, several methods for manufacturing oligosaccharides have been developed, which use matrices with molecular structures (tags) that specifically induce precipitation, partitioning, and adsorption in a particular environment to produce oligosaccharides (Patent Document 6, Non-Patent Documents 12, 13, and 14). These methods combine the advantages of liquid-phase and solid-phase synthesis methods. Specifically, because the reaction can proceed homogeneously, analysis is easier, and the characteristics of the tag allow for separation from reagent residues. For example, it is known to use branched long-chain alkanes as hydrophobic tags and utilize octadecyl-modified silicone to adsorb the reaction solution, thereby separating untagged compounds (Non-Patent Document 14). However, all these methods require the use of tags and have the following drawbacks: a desorption step is required; and as the molecular weight decreases, the matrix becomes larger than the tag, thus the matrix properties gradually become dominant, and the tag's function weakens. Therefore, methods for purifying oligosaccharides more efficiently are needed in the production of oligosaccharide chains. In glycosylation reactions, when the -NHAc group is present in the reaction matrix, the reactivity of the target glycosylation reaction is significantly reduced due to its interaction with Lewis acids, and in most cases, the completion of the reaction requires an excess of sugar donor. Therefore, in the synthesis of oligosaccharide chains containing acetylglucosamine, a method has been adopted in which a Troc group (Non-Patent Documents 5, 6, and 7), a phthalimide group, or a sulfonyl group (Non-Patent Document 4) is used as a temporary protecting group on the nitrogen of glucosamine during the glycosylation reaction, followed by deprotection and then N-Ac glycosylation. However, if a Troc group is used, a zinc / AcOH deprotection reaction condition or an excess of lithium hydroxide and a long reaction time are required, and the complex sugar chain is accompanied by matrix decomposition under the deprotection reaction conditions. Furthermore, in the deprotection process of the phthalimide group, there is a problem that the acetylation of the sialic acid ester site may proceed as a side reaction due to the use of excessive ethylenediamine. To avoid this problem, a two-step deprotection process is required, which involves selectively hydrolyzing the ester site beforehand. Moreover, if the sulfonyl group is used, deprotection is performed under reaction conditions that are difficult to scale up using metallic sodium. Therefore, in the manufacturing method of oligosaccharide chains containing acetylglucosamine, it is necessary to develop a protecting group that does not reduce the reactivity of the glycosylation reaction and can easily replace the acetylation group. Furthermore, polyethylene glycol (PEG), as a biocompatible, water-soluble component, has been widely used in the development of pharmaceuticals and other products in recent years. In the development of these pharmaceuticals, a more homogeneous and high-purity PEG structure is desired; however, commercially available reagents contain numerous impurities, and their purification requires rigorous distillation or complex column purification. Moreover, in compounds with a PEG structure containing an azide structure, distillation operations requiring heating are not suitable due to concerns about potential explosion. Recently, the use of MgCl₂ has been reported... A method for purifying metal complexes of type 2 (Non-Patent Document 15), but due to the need for the target analyte to be adsorbed onto an excess of MgCl₂... Method 2 results in significant losses in the filtrate, suggesting that its purification effect is less efficient compared to single-dissociation methods using crystallization. Therefore, a purification method for compounds with the aforementioned polyethylene glycol structure is desired. In the synthesis of oligosaccharide chains, it becomes increasingly difficult to purify intermediates in crystalline form as the molecular weight increases. In particular, there are no reported examples of crystallization for protected trisaccharides with molecular weights exceeding 1000. Therefore, removing trace amounts of byproducts such as isomers or residual impurities from the starting materials, and other related compounds with similar structures, from the target compound is a significant challenge. Previously, silicone column purification was employed at each step of the synthesis to remove these related compounds, but this has become a major obstacle to achieving efficient mass synthesis. Based on the above background, it is desirable to develop a crystallization and purification method that can efficiently remove impurities with similar structures from oligosaccharide chain synthesis intermediates. (Previous Technical Documents, Patent Documents) Patent Document 1: International Publication No. 2011 / 027868; Patent Document 2: International Publication No. 96 / 02255; Patent Document 3: International Publication No. 2014 / 208742; Patent Document 4: International Publication No. 2017 / 110984; Patent Document 5: International Publication No. 2002 / 16384; Patent Document 6: Japanese Patent No. 6001267; Specification; Non-Patent Documents Non-Patent Literature 1: Proc. Natl. Acad. Sci. USA 2015, 112, 10611-10616 Non-Patent Literature 2: Beilstein J. Org. Chem. 2018, 14, 416-429 Non-Patent Literature 3: Tetrahedron Lett. 1986, 27, 5739-5742 Non-Patent Literature 4: J. Am. Chem. Soc. 2009, 131, 16669-16671 Non-Patent Literature 5: J. Org. Chem. 2016, 81, 10600-10616 Non-Patent Literature 6: J. Am. Chem. Soc. 2019, 141, 6484-6488 Non-Patent Literature 7: Angew. Chem. Int. Ed. Non-patent literature 8: Org. Lett. 2002, 4, 4551 - 4554; Non-patent literature 9: J. Am. Chem. Soc. 2018, 140, 4632-4638; Non-patent literature 10: J. Org. Chem., 2017, 82, 3926-3934; Non-patent literature 11: Angew. Chem. Int. Ed. 2021, 60, 19287-19296; Non-patent literature 12: Journal of the Organic Synthesis Society, 2002, Vol. 60, No. 5, pp. 494-495; Non-patent literature 13: Org. Bio mol. Chem. 2018, 16, 4720-4727; Non-patent literature 14: J. AM. CHEM. SOC. 2005, 127, 7296-7297; Non-Patent Literature 15: Org. Process. Res. Dev. 2021, 25, 10, 2270-2276 [The problem the invention aims to solve] One object of the present invention is to provide a novel oligosaccharide that can be used to manufacture a bibranched polysaccharide having an α2,6-sialic acid structure at a non-reducing end, a method for manufacturing the oligosaccharide, and a method for manufacturing its intermediates and derivatives. Another object of the present invention is to provide a novel oligosaccharide that is a bibranched polysaccharide having an α2,6-sialic acid structure at a non-reducing end, a method for manufacturing the oligosaccharide, and a method for manufacturing its intermediates and derivatives. [Technical Means for Solving the Problem] In order to solve the above-mentioned problems, the inventors conducted intensive research and discovered the novel oligosaccharide represented by A-13 below, a novel method for efficiently producing the oligosaccharide, and intermediates thereof and methods for producing intermediates thereof, as well as the novel oligosaccharide represented by D-13 below, which is a bibranched polysaccharide having an α2,6-sialic acid structure at a non-reducing end, a novel method for efficiently producing the oligosaccharide, and intermediates thereof and methods for producing intermediates thereof, thereby completing the present invention. That is, the invention in this case relates to, but is not limited to, the following. [1] A method for manufacturing an oligosaccharide represented by the following formula A-13, comprising: [Chemical 1] (Step I-1) The step of generating the compound represented by formula A-7 includes: generating the compound represented by formula A-5 by forming an α-1,6-glycosidic bond between the compound represented by formula A-3 and the compound represented by formula A-4; [Chemistry 2] [Chemistry 3] [Chemistry 4] [Chemistry 5] (Step I-2) The step of generating the compound represented by formula A-10 includes: generating the compound represented by formula A-9 by forming a β-1,4-glycosidic bond between the compound represented by formula A-7 and the compound represented by formula A-8; [Chemical 6] [Chemistry 7] [Chemistry 8] (Step I-3) The step of generating the oligosaccharide represented by formula A-13 above includes: generating the compound represented by formula A-12 below by forming a β-1,2-glycosidic bond between the compound represented by formula A-10 above and the compound represented by formula A-11 below. [Chemical 9] [Chemistry 10] [2] The method described in [1] includes step I-2 above, wherein the compound represented by formula A-9 above is reacted with a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid to generate the compound represented by formula A-10 above. [3] The method described in [2] wherein the alkyl ester of the perfluorocarboxylic acid is methyl trifluoroacetate, ethyl trifluoroacetate, propyl trifluoroacetate, isopropyl trifluoroacetate, butyl trifluoroacetate, methyl pentafluoropropionate, ethyl pentafluoropropionate, propyl pentafluoropropionate, isopropyl pentafluoropropionate, methyl heptafluorobutyrate, ethyl heptafluorobutyrate, propyl heptafluorobutyrate, isopropyl heptafluorobutyrate, butyl heptafluorobutyrate, methyl nonafluoropentanoate, ethyl nonafluoropentanoate, propyl nonafluoropentanoate, isopropyl nonafluoropentanoate, butyl nonafluoropentanoate, methyl undecanohexanoate, ethyl undecanohexanoate, propyl undecanohexanoate, isopropyl undecanohexanoate, or butyl undecanohexanoate. [4] The method described in [2] or [3], wherein the strong base is selected from sodium, lithium and potassium salts of metal amides; sodium, lithium, potassium, cesium and barium salts of C1 to C20 alkoxides; sodium hydride, potassium hydride, lithium hydride, butyllithium, potassium carbonate, sodium carbonate, cesium carbonate, lithium carbonate, potassium phosphate, sodium phosphate, cesium phosphate, lithium phosphate, diazabicycloundecene (DBU), diazabicyclononene (DBN), and 1,1,3,3-tetramethylguanidine (TMG); and combinations thereof. [5] The method described in [2] or [3], wherein the strong base is potassium tert-butoxide, sodium tert-butoxide, lithium tert-butoxide, or LHMDS (bis(trimethylsilane)aminolithium). [6] The method described in any one of [2] to [5], wherein the reaction in step I-2 is carried out in the presence of a C1 to C10 alcohol solvent alone or in a mixture of a C1 to C10 alcohol solvent and an amide solvent, an ether solvent, an ester solvent, an aromatic solvent, a halogen solvent, a hydrocarbon solvent, or a nitrile solvent. [7] The method described in any one of [1] to [6], wherein step I-3 includes: reacting the compound represented by formula A-12 with DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone) in a mixture of fluoroalcohol and water to remove the 2-naphthylmethyl group from the compound represented by formula A-12, thereby generating the oligosaccharide represented by formula A-13. [8] The method described in [7], wherein the fluorool is selected from the group consisting of hexafluoro-2-propanol (HFIP), 2,2,2-trifluoroethanol (TFE), 2,2,3,3,4,4,5,5-octafluoro-1-pentanol, nonafluoro-tert-butanol, and combinations thereof. [9] The method described in [7] or [8], wherein the reaction in step I-3 is carried out at -35°C to 70°C.

[10] The method described in [7] or [8], wherein the reaction in step I-3 is carried out at -30°C to -10°C.

[11] The method described in any of [1] to

[10] includes, in step I-1: after terminating the reaction between the compound represented by formula A-4 and the compound represented by formula A-3, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by formula A-5 and the impurities, so that the compound represented by formula A-5 is adsorbed in the hydrophobic carrier, then filtering, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and the water to remove the impurities, and then using an organic solvent to dissolve the compound represented by formula A-5 from the hydrophobic carrier, thereby purifying the compound represented by formula A-5.

[12] The method described in any one of [1] to

[11] includes, in step I-2: after terminating the reaction between the compound represented by formula A-7 and the compound represented by formula A-8, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by formula A-9 and the inclusions, so that the compound represented by formula A-9 is adsorbed in the hydrophobic carrier, then filtering, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and the water to remove the inclusions, and then using an organic solvent to dissolve the compound represented by formula A-9 from the hydrophobic carrier, thereby purifying the compound represented by formula A-9.

[13] The method described in any one of [1] to

[12] , wherein steps 1-3 above include: after terminating the reaction between the compound represented by formula A-10 and the compound represented by formula A-11 above, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by formula A-12 above and the inclusions, so that the compound represented by formula A-12 above is adsorbed into the hydrophobic carrier, then filtering, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and the water above to remove the inclusions, and then using an organic solvent to dissolve the compound represented by formula A-12 above from the hydrophobic carrier, thereby purifying the compound represented by formula A-12 above.

[14] The method described in

[11] , wherein the inclusions include sugar compounds other than the compound represented by formula A-5 above, and / or compounds derived from the reaction reagents used to obtain the purified compound above.

[15] The method described in

[12] , wherein the inclusion comprises a sugar compound other than the compound represented by formula A-9, and / or a compound derived from the reaction reagent used to obtain the purified compound.

[16] The method described in

[13] , wherein the inclusion comprises a sugar compound other than the compound represented by formula A-12, and / or a compound derived from the reaction reagent used to obtain the purified compound.

[17] The method described in any one of

[11] to

[16] , wherein the hydrophobic carrier is a resin for reverse phase partition chromatography.

[18] The method described in

[17] , wherein the resin for reverse phase partition chromatography is selected from the group consisting of poly(styrene / divinylbenzene) polymer gel resin, polystyrene-divinylbenzene resin, polyhydroxymethyl acrylate resin, styrene-vinylbenzene copolymer resin, polyvinyl alcohol resin, polystyrene resin, polymethyl acrylate resin, chemically bonded silicone resin, and combinations thereof.

[19] The method described in

[18] wherein the chemically bonded silicone resin is selected from (1) a resin obtained by reacting silicone with a silane coupling agent; (2) a resin obtained by chemically bonding dimethyloctadecyl, octadecyl, trimethyloctadecyl, dimethyl octyl, octyl, butyl, ethyl, methyl, phenyl, cyanopropyl, or aminopropyl to silicone; (3) a resin obtained by chemically bonding dodecyl or triacontyl to silicone; and (4) a group consisting of combinations of (1) to (3) above.

[20] The method described in

[18] wherein the chemically bonded silicone resin is a silicone resin (ODS resin) bonded with octadecyl groups.

[21] In any of the methods described in

[11] to

[20] , the water-soluble organic solvent is a water-soluble alcohol solvent, a water-soluble nitrile solvent, a water-soluble ether solvent, a water-soluble ketone solvent, a water-soluble amide solvent, or a water-soluble sulfide solvent, or a mixed solvent containing at least one of the above-mentioned water-soluble organic solvent systems.

[22] In the method described in

[21] , the water-soluble nitrile solvent is acetonitrile.

[23] In any of the methods described in

[11] to

[21] , the organic solvent used in the dissolution step of dissolving the target substance from the hydrophobic support is a nitrile solvent, an ether solvent, an ester solvent, a ketone solvent, a halogen solvent, an aromatic solvent, or a mixed solvent containing at least one of the above-mentioned solvent systems.

[24] The method described in any of [1] to

[23] , wherein the compound represented by formula A-11 above is produced by a step including the following steps: (step Y-1) the step of generating the compound represented by formula B-4 below, which includes: generating the compound represented by formula B-3 below by forming a β-1,4-glycosidic bond between the compound represented by formula B-1 below and the compound represented by formula B-2 below; [Chemical 11]. [Chemistry 12] [Chemistry 13] [Chemistry 14] (Step Y-2) The step of generating the compound represented by formula B-5 by adding lithium butoxide or lithium pentanol to a solvent containing the compound represented by formula B-4 and benzyl halide or benzyl sulfonate, thereby protecting the hydroxyl groups present in the compound represented by formula B-4 with the help of benzyl groups: [Chemical 15]

[25] The method described in

[24] includes a solvent for the compound represented by formula B-4 and the benzyl halide or benzyl sulfonate as an amide solvent, an ether solvent, an aromatic solvent, a hydrocarbon solvent, a urea solvent, or a mixture of at least one of the above solvent systems.

[26] The method described in

[24] or

[25] further includes the step of purifying the compound represented by formula B-5 by ring-opening the phthalimide group in the compound represented by formula B-5 and then forming a salt with cinconidine, thereby generating a crystalline compound of formula B-6: [Chemical 16] The compound represented by formula B-6 is obtained by separating the crystalline compound from the non-crystalline substance, then adding an acidic aqueous solution and a solvent to remove cinconidine from the compound represented by formula B-6, thereby generating the following formula B-7: [Chemistry 17] The compound represented by the above formula B-5 is purified by circumclosing the phthalimide group of the compound represented by formula B-7.

[27] The method described in any of [1] to

[26] further includes the step of purifying the compound represented by formula A-13 by opening the phthalimide group of the compound represented by formula A-13 and then forming a salt with (R)-(+)-1-(1-naphthyl)ethylamine, thereby generating a crystalline compound of formula A-14: [Chemical 18] The compound represented by formula A-14 is obtained by separating the crystalline compound from the non-crystalline substance, then adding an acidic aqueous solution and a solvent to remove (R)-(+)-1-(1-naphthyl)ethylamine from the compound represented by formula A-14, thereby generating the following formula A-15: [Chemical 19] The compound represented by the above formula A-15 is then cyclically closed by the above-mentioned open-ring phthalimide group, thereby purifying the compound represented by the above formula A-13.

[28] A method for producing an oligosaccharide represented by the following formula D-13, comprising: [Chemical 20] (Step II-1) The step of generating the compound represented by formula D-2 includes: generating the compound represented by formula D-1 by forming an α-1,3-glycosidic bond between the oligosaccharide represented by formula A-13 and the compound represented by formula A-3; [Chem. 21] [Chemistry 22] [Chemistry 23] [Chemistry 24] (Step II-2) The compound represented by formula D-5 is generated. This step includes generating the compound represented by formula D-4 by forming a β-1,2-glycosidic bond between the compound represented by formula D-2 and the compound represented by formula D-3. After generating the compound represented by formula D-5, the amino group in the compound represented by formula D-5 is protected by a protecting group selected from aryloxycarbonyl (COOAr), acetyl (Ac), 2,2,2-trichloroethoxycarbonyl (Troc), and phthalimide (Pht) to generate the compound represented by formula D-6 (where R...). 5 is an aryloxycarbonyl group (COOAr), an acetyl group (Ac), or a 2,2,2-trichloroethoxycarbonyl group (Troc), and R 6 represents a hydrogen atom, or R 5 and R 6 together with the nitrogen atoms bonded thereto form a phthalimide group, or by removing the acetyl group (Ac) from the compound represented by formula D-4 to generate the compound represented by formula D-6 (where R... 5 and R 6. The step of forming an orthophthalimide group together with the nitrogen atom it is bonded to; [Chem. 25] [Chemistry 26] [Chemistry 27] [Chemistry 28] (Step II-3) The following compound, represented by formula D-11, is generated (where M... + The step (which involves sodium ions, lithium ions, potassium ions, or protonated triethylamine cations) includes: reacting the compound represented by formula D-6 above with the following formula D-7: [Chem. 29] The compound represented undergoes β-1,4-glycosidic bonding to form the following formula D-8: [Chem. 30] The compound represented (where R is a compound) 5 is an aryloxycarbonyl group (COOAr), an acetyl group (Ac), or a 2,2,2-trichloroethoxycarbonyl group (Troc), and R 6 represents a hydrogen atom, or R 5 and R 6, together with the nitrogen atom it is bonded to, forms a phthalimide group. Then, the protecting groups of the amine group and the amide group of the alcohol in the compound represented by formula D-8 are removed to generate the following formula D-9: [Chemical 31] The compound represented (where M is a compound) + The steps involve sodium ions, lithium ions, potassium ions, or protonated triethylamine cations; [Chem. 32] (Step II-4) By reacting the compound represented by formula D-11 above with the following formula D-12: [Chemical 33] The step of reacting the compound represented by the above formula D-13 to generate the oligosaccharide represented by the above formula D-13.

[29] The method described in

[28] includes, in step II-1, the following steps: reacting the compound represented by the above formula D-1 with a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid to generate the compound represented by the above formula D-2.

[30] The method described in

[29] wherein the alkyl ester of the perfluorocarboxylic acid is methyl trifluoroacetate, ethyl trifluoroacetate, propyl trifluoroacetate, isopropyl trifluoroacetate, butyl trifluoroacetate, methyl pentafluoropropionate, ethyl pentafluoropropionate, propyl pentafluoropropionate, isopropyl pentafluoropropionate, methyl heptafluorobutyrate, ethyl heptafluorobutyrate, propyl heptafluorobutyrate, isopropyl heptafluorobutyrate, butyl heptafluorobutyrate, methyl nonafluoropentanoate, ethyl nonafluoropentanoate, propyl nonafluoropentanoate, isopropyl nonafluoropentanoate, butyl nonafluoropentanoate, methyl undecanohexanoate, ethyl undecanohexanoate, propyl undecanohexanoate, isopropyl undecanohexanoate, or butyl undecanohexanoate.

[31] The method described in

[29] or

[30] , wherein the strong base is selected from sodium, lithium, and potassium salts of metal amides; sodium, lithium, potassium, cesium, and barium salts of C1-C20 alkoxides; sodium hydride, potassium hydride, lithium hydride, butyllithium, potassium carbonate, sodium carbonate, cesium carbonate, lithium carbonate, potassium phosphate, sodium phosphate, cesium phosphate, lithium phosphate, diazabicycloundecene (DBU), diazabicyclononene (DBN), and 1,1,3,3-tetramethylguanidine (TMG); and combinations thereof.

[32] The method described in

[29] or

[30] , wherein the strong base is potassium terbutoxide, sodium terbutoxide, lithium terbutoxide, or LHMDS (bis(trimethylsilane)aminolithium).

[33] The method described in any of

[29] to

[32] , wherein the step of reacting the compound represented by formula D-1 with a strong base in the presence of trifluoroacetate to generate the compound represented by formula D-2 is carried out in the presence of a C1 to C10 alcohol solvent alone or in a mixture of a C1 to C10 alcohol solvent and an amine solvent, an ether solvent, an ester solvent, an aromatic solvent, a halogen solvent, a hydrocarbon solvent, or a nitrile solvent.

[34] The method described in any of

[28] to

[33] , wherein in step II-3, the compound represented by formula D-6 is generated by protecting the amine group in the compound represented by formula D-5 with an aryloxycarbonyl group (COOAr).

[35] The method described in any of

[28] to

[34] , wherein in step II-3 above, the step of generating the compound represented by the compound represented by formula D-5 above from the compound represented by formula D-6 above is carried out in an aqueous solution of sodium bicarbonate, potassium bicarbonate, disodium hydrogen phosphate, or dipotassium hydrogen phosphate.

[36] The method described in any of

[28] to

[35] wherein the compound represented by the above formula D-12 is obtained by a purification method comprising the steps of adding the following formula E-1 to a solution containing crude compound represented by the above formula D-12: [Chemical 34]. The compound represented (where R is a compound) 7 is a hydrogen atom, a methyl group, or a methoxy group, and it produces the following formula E-2: [Chemistry 35] The crystalline compound represented (where R is a crystalline compound) 7 is the step of (hydrogen atom, methyl, or methoxy group); and the step of isolating the crystalline compound and then extracting the compound represented by formula D-12 from the isolated crystalline compound.

[37] The method described in

[36] wherein the purified compound represented by formula D-12 has a purity of 95% or more when determined by HPLC.

[38] The method described in

[37] wherein the purity is 98% or more.

[39] The method described in any one of

[28] to

[38] includes, in step II-1: after terminating the reaction between the compound represented by formula A-13 and the compound represented by formula A-3, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by formula D-1 and the impurities, so that the compound represented by formula D-1 is adsorbed in the hydrophobic carrier, then filtering, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and the water to remove the impurities, and then using an organic solvent to dissolve the compound represented by formula D-1 from the hydrophobic carrier, thereby purifying the compound represented by formula D-1.

[40] The method described in any of

[28] to

[39] includes, in step II-2: after terminating the reaction between the compound represented by formula D-3 and the compound represented by formula D-4, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by formula D-5 and impurities, so that the compound represented by formula D-5 is adsorbed in the hydrophobic carrier, then filtering, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and the water to remove the impurities, and then using an organic solvent to dissolve the compound represented by formula D-5 from the hydrophobic carrier, thereby purifying the compound represented by formula D-5.

[41] The method described in any of

[28] to

[40] includes, in step II-3: after terminating the reaction between the compound represented by formula D-6 and the compound represented by formula D-7, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by formula D-8 and impurities, so that the compound represented by formula D-8 is adsorbed in the hydrophobic carrier, then filtering, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and the water to remove the impurities, and then using an organic solvent to dissolve the compound represented by formula D-8 from the hydrophobic carrier, thereby purifying the compound represented by formula D-8.

[42] The method described in any of

[28] to

[41] , wherein step II-3 above includes: generating the following formula D-10 by protecting the amino group on formula D-9 above with acetylene: [Chemical 36] The compound represented by the above formula D-10 is added to a water-soluble organic solvent containing the compound represented by the above formula D-10 and the impurities, so that the compound represented by the above formula D-10 is adsorbed in the hydrophobic carrier, then filtered, and the hydrophobic carrier is washed with a mixed solution of the above water-soluble organic solvent and the above water to remove the impurities, and then the compound represented by the above formula D-10 is dissolved from the above hydrophobic carrier using an organic solvent, thereby purifying the compound represented by the above formula D-10.

[43] In the method described in

[39] , the impurities include sugar compounds other than the compound represented by the above formula D-1, and / or compounds derived from the reaction reagents used to obtain the purified compound.

[44] In the method described in

[40] , the impurities include sugar compounds other than the compound represented by the above formula D-5, and / or compounds derived from the reaction reagents used to obtain the purified compound.

[45] The method described in

[41] , wherein the inclusion comprises a sugar compound other than the compound represented by formula D-8, and / or a compound derived from the reaction reagent used to obtain the purified compound.

[46] The method described in

[42] , wherein the inclusion comprises a sugar compound other than the compound represented by formula C-10, and / or a compound derived from the reaction reagent used to obtain the purified compound.

[47] The method described in any one of

[39] to

[46] , wherein the hydrophobic support is a resin for reverse phase partition chromatography.

[48] The method described in

[47] , wherein the resin for reverse phase partition chromatography is selected from the group consisting of poly(styrene / divinylbenzene) polymer gel resin, polystyrene-divinylbenzene resin, polyhydroxymethyl acrylate resin, styrene-vinylbenzene copolymer resin, polyvinyl alcohol resin, polystyrene resin, polymethyl acrylate resin, chemically bonded silicone resin, and combinations thereof.

[49] The method described in

[48] wherein the chemically bonded silicone resin is selected from (1) a resin obtained by reacting silicone with a silane coupling agent; (2) a resin obtained by chemically bonding dimethyloctadecyl, octadecyl, trimethyloctadecyl, dimethyl octyl, octyl, butyl, ethyl, methyl, phenyl, cyanopropyl, or aminopropyl to silicone; (3) a resin obtained by chemically bonding dodecyl or triacontyl to silicone; and (4) a group consisting of combinations of (1) to (3) above.

[50] The method described in

[48] wherein the chemically bonded silicone resin is a silicone resin (ODS resin) bonded with octadecyl groups.

[51] In any of the methods described in

[39] to

[50] , the water-soluble organic solvent is a water-soluble alcohol solvent, a water-soluble nitrile solvent, a water-soluble ether solvent, a water-soluble ketone solvent, a water-soluble amide solvent, or a water-soluble sulfide solvent, or a mixed solvent containing at least one of the above-mentioned water-soluble organic solvent systems.

[52] In the method described in

[51] , the water-soluble nitrile solvent is acetonitrile.

[53] In any of the methods described in

[39] to

[52] , the organic solvent used in the dissolution step of dissolving the target substance from the hydrophobic carrier is a nitrile solvent, an ether solvent, an ester solvent, a ketone solvent, a halogen solvent, an aromatic solvent, or a mixed solvent containing at least one of the above-mentioned solvent systems.

[54] The method described in any of

[28] to

[53] further includes the step of generating a crystalline compound of the following formula D-5-FMA by forming a salt with fumaric acid: [Chemical 37]. The compound represented by the above formula D-5-FMA is then separated and purified from the non-crystalline substance.

[55] A method for manufacturing the following formula B-5: [Chemical 38] The method for representing the compound includes the following steps: [Chemicals 39] (The original text contains a typo and can be omitted.) Lithium tributoxide or lithium tripentoxide is added to the compound represented and the solvent of benzyl halide or benzyl sulfonate, and the hydroxyl group present in the compound represented by formula B-4 is protected by benzyl group.

[56] The method described in

[55] wherein the solvent is an amide solvent, an ether solvent, an aromatic solvent, a urea solvent, a hydrocarbon solvent, or a mixture of at least one of the above solvent systems.

[57] A method for manufacturing a compound represented by formula A-10, comprising the following steps: [Chemical 40] Make the following equation A-9: [Chemistry 41] The compound represented reacts with a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid.

[58] The method described in

[57] wherein the alkyl ester of the perfluorocarboxylic acid is methyl trifluoroacetate, ethyl trifluoroacetate, propyl trifluoroacetate, isopropyl trifluoroacetate, butyl trifluoroacetate, methyl pentafluoropropionate, ethyl pentafluoropropionate, propyl pentafluoropropionate, isopropyl pentafluoropropionate, methyl heptafluorobutyrate, ethyl heptafluorobutyrate, propyl heptafluorobutyrate, isopropyl heptafluorobutyrate, butyl heptafluorobutyrate, methyl nonafluoropentanoate, ethyl nonafluoropentanoate, propyl nonafluoropentanoate, isopropyl nonafluoropentanoate, butyl nonafluoropentanoate, methyl undecanohexanoate, ethyl undecanohexanoate, propyl undecanohexanoate, isopropyl undecanohexanoate, or butyl undecanohexanoate.

[59] The method as described in

[57] or

[58] , wherein the strong base is selected from sodium, lithium, and potassium salts of metal amides; sodium, lithium, potassium, cesium, and barium salts of C1-C20 alkoxides; sodium hydride, potassium hydride, lithium hydride, butyllithium, potassium carbonate, sodium carbonate, cesium carbonate, lithium carbonate, potassium phosphate, sodium phosphate, cesium phosphate, lithium phosphate, diazabicycloundecene (DBU), diazabicyclononene (DBN), and 1,1,3,3-tetramethylguanidine (TMG); and combinations thereof.

[60] The method as described in

[57] or

[58] , wherein the strong base is potassium terbutoxide, sodium terbutoxide, lithium terbutoxide, or LHMDS (bis(trimethylsilane)aminolithium).

[61] The method described in any of

[57] to

[60] , wherein the above reaction is carried out in the presence of a C1-C10 alcohol solvent alone or in a mixture of a C1-C10 alcohol solvent and an amide solvent, an ether solvent, an ester solvent, an aromatic solvent, a halogen solvent, a hydrocarbon solvent, or a nitrile solvent.

[62] A method for producing an oligosaccharide represented by the following formula A-13, comprising the following steps: [Chemical 42] Make the following equation A-12: [Chemistry 43] The compound represented is reacted with DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone) in a mixed solvent of fluoroalcohol and water to remove the 2-naphthylmethyl group from the compound represented by formula A-12.

[63] The method described in

[62] wherein the fluoroalcohol is selected from the group consisting of hexafluoro-2-propanol (HFIP), 2,2,2-trifluoroethanol (TFE), 2,2,3,3,4,4,5,5-octafluoro-1-pentanol, nonafluoro-tert-butanol, and combinations thereof.

[64] The method described in

[62] or

[63] is carried out at -35°C to 70°C.

[65] The method described in

[62] or

[63] is carried out at -30°C to -10°C.

[66] A method for purifying a compound represented by formula A-5, comprising: [Chemical 44] A hydrophobic carrier and water are added to a water-soluble organic solvent containing the compound represented by formula A-5 and impurities, so that the compound represented by formula A-5 is adsorbed into the hydrophobic carrier. The mixture is then filtered, and the hydrophobic carrier is washed with a mixed solution of the water-soluble organic solvent and water to remove the impurities. The compound represented by formula A-5 is then dissolved from the hydrophobic carrier using an organic solvent, thereby purifying the compound represented by formula A-5.

[67] A method for purifying a compound represented by formula A-9, comprising: [Chemical 45] A hydrophobic carrier and water are added to a water-soluble organic solvent containing the compound represented by formula A-9 and impurities, so that the compound represented by formula A-9 is adsorbed into the hydrophobic carrier. The mixture is then filtered, and the hydrophobic carrier is washed with a mixed solution of the water-soluble organic solvent and water to remove the impurities. The compound represented by formula A-9 is then dissolved from the hydrophobic carrier using an organic solvent, thereby purifying the compound represented by formula A-9.

[68] A method for purifying a compound represented by formula A-12, comprising: [Chemical 46] A hydrophobic carrier and water are added to a water-soluble organic solvent containing the compound represented by formula A-12 and impurities, so that the compound represented by formula A-12 is adsorbed into the hydrophobic carrier. Then, filtration is performed, and the hydrophobic carrier is washed with a mixed solution of the water-soluble organic solvent and the water to remove the impurities. Then, an organic solvent is used to dissolve the compound represented by formula A-12 from the hydrophobic carrier, thereby purifying the compound represented by formula A-12.

[69] A method for purifying a compound represented by formula D-1, comprising: [Chemical 47] A hydrophobic carrier and water are added to a water-soluble organic solvent containing the compound represented by formula D-1 and impurities, so that the compound represented by formula D-1 is adsorbed into the hydrophobic carrier. The mixture is then filtered, and the hydrophobic carrier is washed with a mixed solution of the water-soluble organic solvent and water to remove the impurities. Then, an organic solvent is used to dissolve the compound represented by formula D-1 from the hydrophobic carrier, thereby purifying the compound represented by formula D-1.

[70] A method for purifying a compound represented by formula D-5, comprising: [Chemical 48] A hydrophobic carrier and water are added to a water-soluble organic solvent containing the compound represented by formula D-5 and impurities, so that the compound represented by formula D-5 is adsorbed into the hydrophobic carrier. Then, filtration is performed, and the hydrophobic carrier is washed with a mixed solution of the water-soluble organic solvent and the water to remove the impurities. Then, an organic solvent is used to dissolve the compound represented by formula D-5 from the hydrophobic carrier, thereby purifying the compound represented by formula D-5.

[71] A method for purifying a compound represented by formula D-8: [Chemical 49] (where R is in the formula) 5 is an aryloxycarbonyl group (COOAr), an acetyl group (Ac), or a 2,2,2-trichloroethoxycarbonyl group (Troc), and R 6 represents a hydrogen atom, or R 5 and R 6. Together with the nitrogen atoms bonded thereto, they form phthalimide groups, comprising: adding a hydrophobic carrier and water to a water-soluble organic solvent containing the compound represented by formula D-8 and the inclusions, so that the compound represented by formula D-8 is adsorbed in the hydrophobic carrier, followed by filtration, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and the water to remove the inclusions, and then using an organic solvent to dissolve the compound represented by formula D-8 from the hydrophobic carrier, thereby purifying the compound represented by formula D-8.

[72] A method for purifying a compound represented by formula D-10, comprising: [Chemical 50] A hydrophobic carrier and water are added to a water-soluble organic solvent containing the compound represented by formula D-10 and the inclusions, so that the compound represented by formula D-10 is adsorbed into the hydrophobic carrier. Then, filtration is performed, and the hydrophobic carrier is washed with a mixed solution of the water-soluble organic solvent and the water to remove the inclusions. Then, an organic solvent is used to dissolve the compound represented by formula D-10 from the hydrophobic carrier, thereby purifying the compound represented by formula D-10.

[73] In the method described in

[69] , the inclusions include sugar compounds other than the compound represented by formula D-1, and / or compounds derived from the reaction reagents used to obtain the purified compound.

[74] In the method described in

[70] , the inclusions include sugar compounds other than the compound represented by D-5, and / or compounds derived from the reaction reagents used to obtain the purified compound.

[75] The method described in

[71] , wherein the inclusion comprises a sugar compound other than the compound represented by D-8, and / or a compound derived from the reaction reagent used to obtain the purified compound.

[76] The method described in

[72] , wherein the inclusion comprises a sugar compound other than the compound represented by formula D-10, and / or a compound derived from the reaction reagent used to obtain the purified compound.

[77] The method described in any one of

[69] to

[76] , wherein the hydrophobic support is a resin for reverse phase partition chromatography.

[78] The method described in

[77] , wherein the resin for reverse phase partition chromatography is selected from the group consisting of poly(styrene / divinylbenzene) polymer gel resin, polystyrene-divinylbenzene resin, polyhydroxymethyl acrylate resin, styrene-vinylbenzene copolymer resin, polyvinyl alcohol resin, polystyrene resin, polymethyl acrylate resin, chemically bonded silicone resin, and combinations thereof.

[79] The method described in

[78] wherein the chemically bonded silicone resin is selected from (1) a resin obtained by reacting silicone with a silane coupling agent; (2) a resin obtained by chemically bonding dimethyloctadecyl, octadecyl, trimethyloctadecyl, dimethyl octyl, octyl, butyl, ethyl, methyl, phenyl, cyanopropyl, or aminopropyl to silicone; (3) a resin obtained by chemically bonding dodecyl or triacontyl to silicone; and (4) a group consisting of combinations of (1) to (3) above.

[80] The method described in

[79] wherein the chemically bonded silicone resin is a silicone resin (ODS resin) bonded with octadecyl groups.

[81] The method described in any one of

[69] to

[80] , wherein the water-soluble organic solvent is a water-soluble alcohol solvent, a water-soluble nitrile solvent, a water-soluble ether solvent, a water-soluble ketone solvent, a water-soluble amide solvent, a water-soluble sulfide solvent, or a mixed solvent comprising at least one of the above-mentioned water-soluble organic solvent systems.

[82] The method described in

[81] , wherein the water-soluble nitrile solvent is acetonitrile.

[83] The method described in any one of

[69] to

[82] , wherein the organic solvent used in the dissolution step of dissolving the target substance from the hydrophobic support is a nitrile solvent, an ether solvent, an ester solvent, a ketone solvent, a halogen solvent, an aromatic solvent, or a mixture of at least one of the above solvent systems.

[84] A method for generating a compound represented by the following formula D-8: [Chemical 51]. (where R is in the formula) 5 is an aryloxycarbonyl group (COOAr), an acetyl group (Ac), or a 2,2,2-trichloroethoxycarbonyl group (Troc), and R 6 represents a hydrogen atom, or R 5 and R 6, together with the nitrogen atom to which it is bonded, forms a phthalimide group, which includes the following steps: generating the following formula D-6: [Chemical 52] The compound represented (where R is a compound) 5 is an aryloxycarbonyl group (COOAr), an acetyl group (Ac), or a 2,2,2-trichloroethoxycarbonyl group (Troc), and R 6 represents a hydrogen atom, or R 5 and R 6, together with the nitrogen atoms bonded thereto, forms a phthalimide group, and then the compound represented by formula D-6 above is reacted with the following D-7: [Chemical 53] The compound represented by the formula is bonded to a β-1,4-glycosidic bond, thereby generating the compound represented by the formula D-8 above.

[85] As described in

[84] , wherein R 5 is an aryloxycarbonyl group (COOAr).

[86] The method described in

[84] or

[85] comprises: generating formula D-9 by removing the protecting groups of the amine group and the acetylated protecting groups of the alcohol in the compound represented by formula D-8 above: [Chemical 54] The compound represented (where M is a compound) + (Sodium ion, lithium ion, potassium ion, or protonated triethylamine cation).

[87] A method for purifying a compound represented by the following formula D-12, comprising the following steps: [Chem. 55] Add the following formula E-1 to a solution containing the crude compound represented by formula D-12 above: [Chemistry 56] The compound represented (where R is a compound) 7 is a hydrogen atom, methyl group, or methoxy group, and it produces the following formula E-2: [Chem. 57] The crystalline compound represented (where R is a crystalline compound) 7 is the step of (where 7 is a hydrogen atom, methyl, or methoxy group); and the step of isolating the crystalline compound and then extracting the compound represented by formula D-12 from the isolated crystalline compound.

[88] An oligosaccharide represented by the following formula A-13: [Chem. 58]

[89] A compound represented by the following formula A-5: [Chemistry 59]

[90] A compound represented by the following formula A-6: [Chemical 60]

[91] A compound represented by the following formula A-7: [Chemical 61]

[92] A compound represented by the following formula A-9: [Chemistry 62]

[93] A compound represented by the following formula A-10: [Chemistry 63]

[94] A compound represented by the following formula A-11: [Chemistry 64]

[95] A compound represented by the following formula A-12: [Chemistry 65]

[96] A compound represented by the following formula A-14: [Chemistry 66]

[97] A compound represented by the following formula A-15: [Chemistry 67]

[98] A compound represented by the following formula B-4: [Chemistry 68]

[99] A compound represented by the following formula B-5: [Chemistry 69]

[100] A compound represented by the following formula B-6: [Chemical 70]

[101] A compound represented by the following formula B-7: [Chemistry 71]

[102] A compound represented by the following formula B-8: [Chemistry 72]

[103] A compound represented by the following formula D-1: [Chemistry 73]

[104] A compound represented by the following formula D-2: [Chemistry 74]

[105] A compound represented by the following formula D-4: [Chemistry 75]

[106] A compound represented by the following formula D-5: [Chemistry 76]

[107] A compound represented by the formula D-5-FMA: [Chem. 77]

[108] A compound represented by the following formula D-6: [Chemistry 78] (where R is in the formula) 5 is an aryloxycarbonyl group (COOAr), an acetyl group (Ac), or a 2,2,2-trichloroethoxycarbonyl group (Troc), and R 6 represents a hydrogen atom, or R 5 and R 6 together with the nitrogen atom to which it is bonded forms a phthalimide group.

[109] A compound represented by the following formula D-8: [Chemical 79] (where R is in the formula) 5 is an aryloxycarbonyl group (COOAr), an acetyl group (Ac), or a 2,2,2-trichloroethoxycarbonyl group (Troc), and R 6 represents a hydrogen atom, or R 5 and R 6 together with the nitrogen atom to which it is bonded forms a phthalimide group.

[110] A compound represented by the following formula D-9: [Chemical 80] (where M is in the formula) + (Sodium ion, lithium ion, potassium ion, or protonated triethylamine cation).

[111] A compound represented by the following formula D-10: [Chemical 81] (where M is in the formula) + (Sodium ion, lithium ion, potassium ion, or protonated triethylamine cation).

[112] A compound represented by the following formula D-11: [Chem. 82] (where M is in the formula) + (Sodium ion, lithium ion, potassium ion, or protonated triethylamine cation).

[113] A compound represented by the following formula E-2: [Chemistry 83] (where R is in the formula) 7 is a hydrogen atom, methyl group, or methoxy group.

[114] A compound represented by the following formula D-12 and having a purity of more than 90% when determined by HPLC: [Chemistry 84]

[115] The compound as described in claim 109, wherein the purity is 95% or higher.

[116] An oligosaccharide represented by the following formula D-13: [Chemical 85] [Effects of the Invention] The present invention provides an oligosaccharide represented by formula A-13 above and a novel method for manufacturing the same, as well as an intermediate for manufacturing the same oligosaccharide and a method for manufacturing the same, and an oligosaccharide represented by formula D-13 above and a novel method for manufacturing the same oligosaccharide and an intermediate for manufacturing the same. The following describes suitable embodiments for carrying out the present invention. Furthermore, the embodiments described below are merely examples of representative embodiments of the present invention and are not intended to limit the scope of the invention. <1. Method for Manufacturing Oligosaccharides Represented by Formula A-13> In one embodiment of the present invention, a novel oligosaccharide represented by Formula A-13 and a novel method for manufacturing the same are provided. In the present invention, the oligosaccharide represented by Formula A-13 refers to the following oligosaccharide. [Chemical 86] The novel synthetic process of the oligosaccharide represented by the above formula A-13 includes the following steps I-1 to I-3. <Step I-1> Step I-1 is the step of generating the compound represented by formula A-7, which includes: generating the compound represented by formula A-5 by forming an α-1,6-glycosidic bond between the compound represented by formula A-3 and the compound represented by formula A-4. [Chemistry 87] [Chemistry 88] [Chemistry 89] [Chemistry 90] Step I-1 includes the following steps I-1-1 to I-1-3. <Step I-1-1> Step I-1-1 is the step of producing the compound represented by formula A-5 by forming an α-1,6-glycosidic bond between the compound represented by formula A-3 and the compound represented by formula A-4. This step can be carried out by using or applying known methods, but it is preferred to be carried out by, for example, the method shown in Example 22, such as sequentially adding molecular sieve 4A powder and trimethylsilane trifluoromethanesulfonate (TMSOTf) to an organic solvent (toluene, etc.) to form an α-1,6-glycosidic bond between the compound represented by formula A-3 and the compound represented by formula A-4, thereby generating the compound represented by formula A-5. Furthermore, the compound represented by formula A-3 and the compound represented by formula A-4, as starting materials, can be manufactured in the following manner. <Preparation of the compound represented by formula A-3> In one embodiment of the present invention, the compound represented by formula A-3 can be prepared by the following steps, but is not limited to the preparation method. First, for the following equation A-1: ​​[Chemistry 91] The compound represented (3,4,6-tris-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannose), for example, with the addition of water and TsOH·H 2O, then reacts with triethylamine to produce the following formula A-2: [Chem. 92] The compound represented. This step is preferably performed by, for example, the method shown in Example 1. Subsequently, trichloroacetonitrile and diazabicycloundecene (DBU) are added to the compound represented by formula A-2, thereby producing the compound represented by formula A-3. This step is preferably carried out by, for example, the method shown in Example 2. <Preparation of the Compound Represented by Formula A-4> In one embodiment of the present invention, the compound represented by Formula A-4 is prepared by steps X-1 to X-14 below, or steps X-1 to X-8 + X-15 to X-16 below. Details of each step are illustrated below, but each step can be carried out using conventional methods for the preparation of monosaccharides or oligosaccharides, or by applying such conventional methods. [Chemical 93] [Chemistry 94] <Step X-1> Step X-1 is performed by using 2-naphthylmethyl (Nap) to react with the following formula C-1: [Chem. 95] The hydroxyl group bonded to the 3-carbon of the compound represented is protected to produce the following formula C-2: [Chem. 96] The steps involving the compound represented by the formula C-1. The compound represented by formula C-1, which serves as the starting material for this step, can be manufactured by known methods or a commercially available product can be used. Examples of commercially available products representing the compound of formula C-1 include, for instance, 1,2:5,6-di-O-isopropylidene-α-D-furanose glucose manufactured by Sigma-Aldrich. This step can be carried out using or applying known methods, but is preferably carried out by, for example, the method shown in Example 10. <Step X-2> Step X-2 involves the acid hydrolysis of two isopropylidene groups and the formation of a pyranose ring in the compound represented by formula C-2 to produce the following formula C-3: [Chem. 97] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 11. <Step X-3> Step X-3 involves using an acetyl group to protect the hydroxyl group on the compound represented by formula C-3 to produce the following formula C-4: [Chemical 98] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 12. <Step X-4> Step X-4 is achieved by selectively removing the acetyl group from the acetoxy group bonded to the 1-carbon of the compound represented by formula C-4, to produce the following formula C-5: [Chem. 99] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 12. The steps for producing the compound represented by formula C-5 from the compound represented by formula C-3 can be, for example, as shown in Example 12, by means of a single-tank method. <Step X-5> Step X-5 involves reacting the compound represented by formula C-5 with trichloroacetonitrile to produce the following formula C-6: [Chemistry 100] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 13. <Step X-6> Step X-6 is achieved by reacting the compound represented by formula C-6 with the following formula C-7: [Chemistry 101] The compound represented reacts to produce the following formula C-8: [Chemical 102] The steps for producing the compound represented by Formula C-7. The compound represented by Formula C-7 can be manufactured by known methods or commercially available products can be used. Examples of commercially available products representing the compound of Formula C-7 include 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimide-β-D-glucopyranoside manufactured by Tokyo Chemical Industries, Ltd. This step can be carried out using or applying known methods, preferably by, for example, the method shown in Example 14. <Step X-7> Step X-7 involves removing the acetyl group from the compound represented by formula C-8 to produce the following formula C-9: [Chemical 103] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 15. In one embodiment of the present invention, step X-7 involves reacting the compound represented by formula C-8 with a strong base in the presence of trifluoroacetate to remove the acetyl group and generate the compound represented by formula C-9. The removal of the acetyl group using sodium methoxide in methanol has been reported (Org. Bio mol. Chem., 2018, 16, 4720-4727), but in this case, the undesirable side reaction of ring-opening of the phthalimide group may also occur simultaneously. On the other hand, by using a reaction with a strong alkoxide-based base in the presence of an alkyl ester of a perfluorocarboxylic acid, the ring-opening of the phthalimide group can be suppressed while the acetyl group is removed. There are no restrictions on the "alkyl esters of perfluorocarboxylic acids" used in the above steps, as long as the reaction proceeds. These include methyl trifluoroacetate, ethyl trifluoroacetate, propyl trifluoroacetate, isopropyl trifluoroacetate, butyl trifluoroacetate, methyl pentafluoropropionate, ethyl pentafluoropropionate, propyl pentafluoropropionate, isopropyl pentafluoropropionate, methyl heptafluorobutyrate, ethyl heptafluorobutyrate, propyl heptafluorobutyrate, isopropyl heptafluorobutyrate, butyl heptafluorobutyrate, methyl nonafluoropentanoate, ethyl nonafluoropentanoate, propyl nonafluoropentanoate, isopropyl nonafluoropentanoate, butyl nonafluoropentanoate, methyl undecanoic acid, ethyl undecanoic acid, propyl undecanoic acid, isopropyl undecanoic acid, and butyl undecanoic acid. Methyl trifluoroacetate is preferred. There are no restrictions on the type of "strong base" used, as long as the reaction proceeds. Examples include sodium, lithium, and potassium salts of metalloamines; sodium, lithium, potassium, cesium, and barium salts of C1-C20 alkoxides; sodium hydride, potassium hydride, lithium hydride, butyllithium, potassium carbonate, sodium carbonate, cesium carbonate, lithium carbonate, potassium phosphate, sodium phosphate, cesium phosphate, lithium phosphate, diazabicycloundecene (DBU), diazabicyclononene (DBN), and 1,1,3,3-tetramethylguanidine (TMG). ; and groups consisting of combinations thereof, such as sodium, lithium, and potassium salts of C1 to C20 alkoxides, including: lithium methoxide, sodium methoxide, potassium methoxide, lithium ethoxide, sodium ethoxide, potassium ethoxide, lithium isopropoxide, lithium isopropoxide, potassium isopropoxide, lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide, lithium tert-pentoxide, sodium tert-pentoxide, or potassium tert-pentoxide, with particularly preferred examples including sodium tert-butoxide, lithium tert-butoxide, potassium tert-butoxide, and LHMDS (bis(trimethylsilane)aminolithium). There are no restrictions on the solvent used in this step, as long as the reaction proceeds. For example, a C1-C10 alcohol solvent can be used alone, or a mixture of a C1-C10 alcohol solvent with an amide solvent (dimethylformamide, dimethylacetamide, etc.), an ether solvent (tetrahydrofuran, dimethoxyethane, cyclopentyl methyl ether, etc.), an ester solvent (ethyl acetate, etc.), an aromatic solvent (toluene, etc.), a halogen solvent (dichloromethane, etc.), a hydrocarbon solvent (hexane, etc.), or a nitrile solvent (acetonitrile, etc.). Methanol, or a mixture of methanol and tetrahydrofuran, is preferred, but it is not limited to these. Furthermore, the aforementioned "C1-C10 alcohol solvent" can also be replaced with an alcohol with more carbon atoms. On the other hand, in terms of ease of acquisition or convenience, C1-C5 alcohols (methanol, ethanol, propanol, butanol, etc.) are preferred. There is no limitation on the reaction temperature in this step, as long as the reaction proceeds. For example, -20℃ to 80℃ is acceptable, 0℃ to 70℃ is preferable, 20℃ to 65℃ is even better, and 40℃ to 60℃ is particularly desirable. <Step X-8> Step X-8 involves using benzaldehyde dimethyl acetal to selectively protect the hydroxyl groups bonded at the 4 and 6 carbons of the D-glucopyranoside in the compound represented by formula C-9, thereby producing the following formula C-10: [Chemical 104] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 16. <Step X-9> Step X-9 involves reacting a compound represented by formula C-10 with a compound endowed with a dissociative group selected from the group consisting of trifluoromethanesulfonyloxy, nonafluorobutyroxy, 2-nitrobenzenesulfonyloxy, and 4-nitrobenzenesulfonyloxy to produce the following formula C-11: [Chemical 105] The compound represented (where X is a compound) 1 indicates the step of selecting a substituent from the group consisting of trifluoromethanesulfonyl, nonafluorobutyryl, 2-nitrobenzenesulfonyl, and 4-nitrobenzenesulfonyl. This step can be carried out by using or applying a known dissociation group-donating method, preferably by, for example, the method shown in Example 17. In this step, "a compound selected from the group consisting of trifluoromethanesulfonyloxy, nonafluorobutyroxy, 2-nitrobenzenesulfonyloxy, and 4-nitrobenzenesulfonyloxy" is given a detached group. Examples include trifluoromethanesulfonic anhydride, nonafluoro-1-butyroxy-fluorine, bis(nonafluoro-1-butyroxy) anhydride, 2-nitrobenzenesulfonyl chloride, or 4-nitrobenzenesulfonyl chloride. Trifluoromethanesulfonic anhydride is a preferred example. There are no restrictions on the solvent used in this step, as long as the reaction proceeds. Examples of solvents include ethyl acetate, toluene, dichloromethane, acetonitrile, cyclopentyl methyl ether, or tributyl methyl ether. Preferred solvents include ethyl acetate, toluene, or dichloromethane. There is no limitation on the reaction temperature in this step, as long as the reaction proceeds. For example, -40℃ to 60℃ is acceptable, -30℃ to 40℃ is preferred, and -20℃ to 10℃ is even more desirable. This step is preferably carried out in the presence of a base. There are no particular limitations on the base used in this step, as long as the reaction proceeds. Examples of bases include 1-methylimidazole, pyridine, 4-dimethylaminopyridine, methylpyridine, dimethylpyridine, or trimethylpyridine, with 1-methylimidazole being a preferred example. <Step X-10> Step X-10 involves reacting the compound represented by formula C-11 with cesium acetate or tetrabutylammonium acetate to produce the following formula C-12: [Chemical 106] The compound represented (where X is a compound) 2 is acetyl), or the following formula C-12 can be prepared by reacting the compound represented by formula C-11 with tetrabutylammonium benzoate: [Chemical 107] The compound represented (where X is a compound) Step 2 (with benzoyl). The stereoinversion of glucose to mannose is a well-known inversion reaction, but there are no reports of inversions where the protecting group of the hydroxyl group at the 3-carbon bond of the D-glucopyranoside of the glucose-glucosamine 2-glycoside linked by a β-glycosidic bond is 2-naphthylmethyl (Nap). Using this method, the stereoinversion of glucose to mannose can be achieved, and the mannose-glucosamine 2-glycoside backbone linked by a β-glycosidic bond can be constructed with high yield and high selectivity. There are no restrictions on the solvent used in this step, as long as the reaction proceeds. Examples include: dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, N,N-dimethylimidazolidineone, cyclobutane, tetrahydrofuran, or acetonitrile. Dimethyl sulfoxide is a preferred solvent. There is no limit to the reaction temperature in this step, as long as the reaction proceeds. For example, 20℃~80℃ is acceptable, 23℃~70℃ is preferred, 26℃~60℃ is even better, and 30℃~50℃ is especially desirable. <Step X-11> Step X-11 is achieved by using the compound represented by formula C-12 to make X The 2-group is removed, and the phthalimide group is simultaneously opened to produce the following formula C-13: [Chemical 108] The steps for representing the compound. This step can be carried out by using or applying known hydrolysis methods, preferably by, for example, the method shown in Example 18. In this step, the compound represented by formula C-13 can be dissolved in a solvent and used directly in the next step, or it can be isolated and purified by recrystallization. A major advantage of the compound represented by formula C-13 is that it can be isolated and purified by crystallization, which almost completely removes impurities with similar structures that are difficult to remove by column purification. In this case, a compound represented by formula C-13 with an HPLC purity of over 99% can be obtained. The separation and purification using recrystallization in this step can be exemplified by the following methods: completely removing the solvent from its dissolved state by vacuum drying; or using tetrahydrofuran as a good solvent and adding isopropanol as a poor solvent in the presence of a trace amount of water. The recrystallization in this step can also be performed using a seed crystal of the compound represented by formula C-13. When using a seed crystal, crystallization can be performed, for example, by using tetrahydrofuran as a good solvent and adding a portion of isopropanol as a poor solvent in the presence of a trace amount of water. After adding the seed crystal, confirm that crystals have precipitated, and then add the remaining isopropanol. The steps for producing the compound represented by formula C-13 from the compound represented by formula C-11 can be performed, for example, by the single-tank method as shown in Example 18. <Step X-12> Step X-12 involves closing the open-ring phthalimide group in the compound represented by formula C-13 through dehydration condensation to produce the following formula C-14: [Chemical 109] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 19. <Step X-13> Step X-13 involves protecting the hydroxyl group at the 2-carbon position of the D-mannopyranoside in the compound represented by formula C-14 with a benzyl group to produce the following formula C-15: [Chemical 110] The steps for representing the compound. This step can be carried out by using or applying known methods, and preferably by, for example, the method shown in Example 20. In one embodiment of the present invention, step X-13 includes the following step: in the presence of lithium butoxide or lithium pentanol, using a benzyl group to protect the hydroxyl group bonded to the 2-carbon of the D-mannopyranoside in the compound represented by formula C-14, thereby producing the compound represented by formula C-15. By carrying out step X-15 in the presence of lithium butoxide or lithium pentanol, the ring-opening of phthalimide can be suppressed. Furthermore, compared with the general conditions using sodium hydride, it can be carried out safely and is easy to scale up. There are no restrictions on the solvent used in this step, as long as the reaction proceeds. Examples of solvents include dimethylacetamide, dimethylformamide, N-methylpyrrolidone, and N,N-dimethylimidazolidineone. Dimethylacetamide is a preferred solvent. There is no limit to the reaction temperature in this step, as long as the reaction proceeds. For example, -20℃ to 100℃ is acceptable, -15℃ to 70℃ is preferable, and -10℃ to 50℃ is even more desirable. <Step X-14> Step X-14 is achieved by selectively reducing the benzylidene protecting group in the compound represented by formula C-15 (for more details, see Angew. Chem. Int. Ed. 2005, 44, 1665-1668) to produce the following formula A-4, in which only the hydroxyl group bonded to the 6-carbon of D-mannopyranoside is deprotected: [Chem. 111] The steps for representing the compound. This step can be carried out by using or applying known methods, but is preferably carried out by, for example, the method shown in Example 21. In this step, the compound represented by formula A-4 can be dissolved in a solvent and used directly in the next step, or it can be isolated and purified by column purification or other methods. In one embodiment of the present invention, instead of including the method for utilizing S N Steps X-9 to X-12, which carry out the stereoinversion of glucose to mannose, include steps X-15 and X-16 shown below, which utilize redox reactions to achieve the stereoinversion of glucose to mannose. [Chem. 112] <Step X-15> Step X-15 involves oxidizing the D-glucopyranoside at the 2-position in the compound represented by formula C-10 to produce the following formula C-16: [Chemical 113] The steps for representing the compound. This step can be performed by using or applying known methods. <Step X-16> Step X-16 is to produce the following formula C-14 by reducing the ketone group bonded to the 2-carbon of 2-keto-D-glucopyranoside in the compound represented by formula C-16: [Chemical 114] The steps for representing the compound. This step can be performed by using or applying known methods. There are no restrictions on the solvent used in this step, as long as the reaction proceeds. Examples include: diethyl ether, cyclopentyl methyl ether, tributyl methyl ether, diisopropyl ether, dipropyl ether, dibutyl ether, 1,4-dimethyl ether, and preferably tetrahydrofuran. There is no limitation on the reaction temperature for this step, as long as the reaction proceeds; for example, -80℃ to 20℃ can be used. Furthermore, as described below, the optimal reaction temperature varies depending on the reducing agent used. In one embodiment of the present invention, the side oxygen group bonded to the 2-carbon of the 2-keto-D-glucopyranoside in the compound represented by formula C-16 is selected from L-tris(2-butylboronylhydride), L-tris(2-butylboronylhydride), lithium diisobutyl-tert-butoxyaluminum hydride (LDBBA), and the following formula W: [Chemical 115] The compound represented (where R is a compound) 3 is represented by the following formula: [Chemistry 116] The term represents di-tert-butylmethylbenzene oxide or hydride, but with at least two Rs. 3 is reduced in the presence of a reducing agent from the group consisting of di-tert-butylmethylbenzene oxide and combinations thereof. In this reduction step, for example, NaBH2 is used... In case 4, the stereoselectivity is low (around 7:3), making it difficult to efficiently obtain the desired stereoreversal of Gln→Man (Org. Biomol. Chem., 2018, 16, 4720 - 4727). On the other hand, when using the reducing agents listed above, compared to using NaBH... Compared to case 4, the selectivity of stereo inversion of Gln→Man is significantly improved (93.6:6.4~98.1:1.9). The compound represented by formula W contains 3 Rs. Compounds of 3-di-tert-butylmethylbenzene oxide can be obtained, for example, by adding dibutylhydroxytoluene (885.41 mg, 4.02 mmol) to a tetrahydrofuran suspension (2 mL) of lithium aluminum hydride (50.0 mg, 1.32 mmol) at 0°C and then stirring at 25°C. The compounds represented by formula W contain two R... The compound of 3-di-tert-butylmethylbenzene oxide can be obtained by using 2 molar equivalents of dibutylhydroxytoluene relative to 1 molar equivalent of lithium aluminum hydride in the same manner. As described above, the reaction temperature in this step is not limited, as long as the reaction proceeds. When using L-tris(2-butylboronylhydride), LS-tris(2-butylboronylhydride), or LDBBA as the reducing agent, the reaction temperature is preferably -80°C to -20°C, more preferably -80°C to -30°C, further preferably -80°C to -40°C, and even more preferably -80°C to -50°C. When using the compound represented by formula A as the reducing agent, the reaction temperature is preferably -20°C to 20°C, more preferably -15°C to 15°C, and even more preferably -10°C to 10°C. Therefore, in terms of allowing the reaction to proceed at a more easily operable temperature, the reducing agent used in this step is preferably the compound represented by formula W. <Purification of the Compound Represented by A-5> In step I-1-1, the compound represented by formula A-5 can be obtained in its purified form by the following purification method. This purification method includes: after terminating the reaction between the compound represented by formula A-4 and the compound represented by formula A-3, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by formula A-5 and impurities, causing the compound represented by formula A-5 to be adsorbed onto the hydrophobic carrier; then filtering; washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and water to remove impurities; and then using an organic solvent to dissolve the compound represented by formula A-5 from the hydrophobic carrier, thereby purifying the compound represented by formula A-5. Following this purification method, a small amount of hydrophobic carrier is used in the liquid-phase synthesis of oligosaccharide chains to wash away reagent residues or impurities derived from sugar donors and acceptors after the glycosylation reaction. This facilitates easy removal and inhibits reaction inhibition and side reactions caused by such impurities, thus enabling the large-scale and efficient production of high-quality oligosaccharides. Furthermore, compared to previously developed methods, this invention, by utilizing the inherent hydrophobicity of the matrix, reduces the number of tag desorption steps and prevents the functional degradation of the tag during low-molecular-weight degradation, allowing for more efficient oligosaccharide production. In particular, in this step, the purification method described above allows for the easy separation and purification of the compound represented by Formula A-5 from the decomposition products derived from the compound represented by Formula A-3. Furthermore, the purification of the compound represented by formula A-5 is not limited to the purification in step I-1-1. Therefore, in one embodiment of the present invention, a method is also provided, comprising: adding a hydrophobic carrier and water to a water-soluble organic solvent containing the compound represented by formula A-5 and impurities, so that the compound represented by formula A-5 is adsorbed into the hydrophobic carrier, followed by filtration, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and water to remove impurities, and then using an organic solvent to dissolve the compound represented by formula A-5 from the hydrophobic carrier, thereby purifying the compound represented by formula A-5. Furthermore, the above purification method can also be applied to the purification of organic compounds other than sugar compounds. Furthermore, when the organic compound to be purified is a sugar compound, it is preferable to purify a protected oligosaccharide with a sugar chain structure containing 3 to 15 sugar residues, in which some or all of the hydroxyl groups in the sugar are protected. The protecting group of the sugar chain at this time includes alkyl ethers, benzyl ethers, silyl ethers, esters, carbonates, but is not limited to them. The term "impurities" refers to compounds or reagents other than the protected oligosaccharide (the compound represented by formula A-5 in this step). It mainly refers to reagents or their residues used in the synthesis reaction of the protected oligosaccharide, monosaccharide or disaccharide compounds used in the extension reaction of the protected oligosaccharide, or byproducts generated by the deprotection reaction of the protected oligosaccharide. The aforementioned "hydrophobic carrier" refers to a hydrophobic adsorbent material that adsorbs onto a specific compound containing sugar compounds. For example, resins used in reverse phase partition chromatography can be cited. "Resins used in reverse phase partition chromatography" are selected from the group consisting of poly(styrene / divinylbenzene) polymer gel resins, polystyrene-divinylbenzene resins, polyhydroxymethyl acrylate resins, styrene-vinylbenzene copolymer resins, polyvinyl alcohol resins, polystyrene resins, polymethyl acrylate resins, chemically bonded silicone resins, and combinations thereof, but are not limited to them. The above-mentioned "chemically bonded silicone resin" is selected from (1) a resin obtained by reacting silicone with a silane coupling agent; (2) a resin obtained by chemically bonding dimethyloctadecyl, octadecyl, trimethyloctadecyl, dimethyl octyl, octyl, butyl, ethyl, methyl, phenyl, cyanopropyl, or aminopropyl to silicone; (3) a resin obtained by chemically bonding dodecyl or triacontyl to silicone; and (4) the group consisting of combinations of (1) to (3) above. It is preferred to use silicone resin (ODS resin) bonded with octadecyl, but it is not limited to these. The above-mentioned "water-soluble organic solvent" is not particularly limited. Water-soluble alcohol solvents (preferably C1 to C4), water-soluble nitrile solvents (acetonitrile, etc.), water-soluble ether solvents (tetrahydrofuran, etc.), water-soluble ketone solvents (acetone, etc.), water-soluble amide solvents (dimethylformamide, etc.), or water-soluble sulfide solvents (dimethyl sulfide, etc.) can be used. Acetonitrile is preferred. The "organic solvent" used in the dissolution step of dissolving the target substance from the above-mentioned hydrophobic support is not particularly limited. Nitrile solvents (acetonitrile, etc.), ether solvents (tetrahydrofuran, etc.), ester solvents (ethyl acetate, etc.), ketone solvents (acetone, etc.), halogen solvents (dichloromethane, etc.), or aromatic solvents (toluene, etc.), or mixed solvents containing at least one of the above solvent systems, are preferred. Acetonitrile, ethyl acetate, tetrahydrofuran, and toluene are preferred. The purification steps described above are not particularly limited and can be carried out at temperatures ranging from 0°C to 50°C. After step I-1-1 above, the compound represented by formula A-7 above can be manufactured from the compound represented by formula A-5 above by the following steps I-1-2 to I-1-3, but is not limited to these manufacturing steps. <Step I-1-2> Step I-1-2 involves deprotecting 4-methoxyphenyl with the compound represented by formula A-5 above to generate formula A-6 [Chemical 117] The steps of the compound represented. In one embodiment of the present invention, this step involves reacting the compound represented by formula A-5 with λ3-iodine in fluoroalcohol and water to deprotect the 4-methoxyphenyl compound, thereby generating the compound represented by formula A-6. This step is preferably performed by, for example, the method shown in Example 23. The term "λ3-iodine" refers to a trivalent superatomic iodine compound. In one embodiment, it is of formula R. 4 -I(OR 5 ) The compound represented by 2 (where R is a compound) 4 R is an unsubstituted or substituted phenyl group. 5 The group consisting of H, acetoxy, trifluoroacetoxy, toluenesulfonoxy, methanesulfonoxy, and combinations thereof. As defined in the above formula, R 4The substituent can also be a "substituted phenyl group," and examples of substituents include: straight-chain or branched saturated or unsaturated hydrocarbon groups, oxygen-containing groups (alkoxy groups, esters, etc.), nitrogen-containing groups (cyano groups, azides, etc.), halogen atoms (e.g., fluorine atoms, chlorine atoms, bromine atoms, iodine atoms), etc., and more preferably hydrocarbon groups, oxygen-containing substituents, and halogen atoms. When such substituents contain carbon, for example, those having 1 to 5 carbons or 1 to 3 carbons can be used. Specific examples of λ3-iodine include: [bis(trifluoroacetoxy)iodine]benzene (PIFA), [hydroxy(toluenesulfonoxy)iodine]benzene (HTIB), (diacetoxyiodine)benzene (PIDA), [bis(trifluoroacetoxy)iodine]pentafluorobenzene, and [hydroxy(methanesulfonoxy)iodine]benzene, but it is not limited to these. The term "fluoroalcohol" as used in the above steps refers to a fluorinated alcohol compound in which all carbon atoms except the carbon atom bonded to the alcohol are fluorinated. Fluorinated alcohols are preferably those with more fluorine atoms, provided that fluorine substitution is permissible. Fluorinated alcohols include, but are not limited to, fluoroaliphatic alcohols. The hydrocarbon moiety in fluoroaliphatic alcohols can be saturated or unsaturated, linear or branched, or cyclic. Examples of fluoroaliphatic alcohols include fluorinated C4567 ... 2~C 8. Aliphatic alcohols, preferably fluorinated C 2~C 5. Aliphatic alcohols, preferably fluorinated C 2~C 3. Aliphatic alcohols. Specific examples of fluoroalcohols include, but are not limited to, the group consisting of hexafluoro-2-propanol (HFIP), 2,2,2-trifluoroethanol (TFE), 2,2,3,3,4,4,5,5-octafluoro-1-pentanol, nonafluoro-tert-butanol, and combinations thereof. This step is carried out in the presence of the aforementioned fluorohydrin and "water". The amount of water can be appropriately set from the viewpoint of achieving a high yield of the product, for example, relative to the compound represented by Formula A-5, it can be about 1.0 equivalent or more, about 1.5 equivalent or more, about 2.0 equivalent or more, or about 2.5 equivalent or more in molar ratio, and relative to the compound represented by Formula A-5, it can be about 10 or less, about 8 or less, about 5 or less, or about 3 or less in volume ratio. In this step, an "additive" may be added to the fluorohydrin and water. The additive is preferably selected from the group consisting of sodium dihydrogen phosphate, potassium dihydrogen phosphate, disodium hydrogen phosphate, trifluoroacetic acid, and combinations thereof. The amount of the additive can be appropriately set, for example, relative to the compound represented by formula A-5, it can be about 0.5 to 8 equivalents, about 1 to 6 equivalents, or about 1.5 to 5 equivalents. <Step I-1-3> Step I-1-3 is the step of generating the compound represented by formula A-7 from the compound represented by formula A-6 above. This step can be carried out by using or applying known methods, and is preferably carried out by, for example, the method shown in Example 24. In one embodiment of the present invention, this step involves reacting the compound represented by formula A-6 with 2,2,2-trifluoro-N-phenyliminoacetyl chloride (TFPC) in the presence of DBU to generate the compound represented by formula A-7. By using DBU as the base to be used, the equivalent amount of TFPC can be reduced compared to using, for example, potassium carbonate, thus achieving a high yield of the target compound. TFPC is a high-value reagent, therefore, the increased yield of this step is highly beneficial for commercial production. There are no restrictions on the solvent used in this step, as long as the reaction proceeds. Examples include dichloromethane, toluene, ethyl acetate, acetonitrile, or tetrahydrofuran, with dichloromethane being a preferred example. There is no limit to the reaction temperature in this step, as long as the reaction proceeds. The preferred temperature is -20℃ to 40℃, more preferably -10℃ to 35℃, and even more preferably 0℃ to 30℃. This step is preferably carried out in the presence of a dehydrating agent. There are no restrictions on the dehydrating agent used in this step, as long as the reaction proceeds. For example, molecular sieves can be used, and preferably, molecular sieve 4A powder with a particle size of less than 10 μm can be used. In this step, the compound represented by A-7 can be dissolved in a solvent and used directly in the next step, or it can be isolated and purified by column chromatography, provided that the base used in the reaction is removed. Examples of column chromatography for isolation and purification include using silicone as the stationary phase and a mixture of dichloromethane or toluene-ethyl acetate as the mobile phase. <Step I-2> Step I-2 is the step of generating the compound represented by the following formula A-10, which includes: reacting the compound represented by the above formula A-7 with the following formula A-8: [Chemical 118] The compound represented undergoes β-1,4-glycosidic bonding to form the following formula A-9: [Chemistry 119] The steps involved in producing the compound; [Chemistry 120] Step I-2 includes the following steps I-2-1 to I-2-2. <Step I-2-1> Step I-2-1 is the step of generating the compound represented by formula A-9 by forming a β-1,4-glycosidic bond between the compound represented by formula A-7 and the compound represented by formula A-8. The compound represented by formula A-8 can be manufactured by known methods or a commercially available product can be used. Examples of commercially available products representing formula A-8 include 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimide-β-D-glucopyranoside manufactured by Tokyo Chemical Industry Co., Ltd. This step can be carried out using known methods, but is preferably carried out by, for example, the method shown in Example 25. <Purification of the Compound Represented by Formula A-9> In step I-2-1, the compound represented by Formula A-9 can be obtained in its purified form by the following purification method. This purification method includes: after terminating the reaction between the compound represented by Formula A-7 and the compound represented by Formula A-8, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by Formula A-9 and impurities, causing the compound represented by Formula A-9 to be adsorbed onto the hydrophobic carrier; then filtering; washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and water to remove impurities; and then using an organic solvent to dissolve the compound represented by Formula A-9 from the hydrophobic carrier, thereby purifying the compound represented by Formula A-9. Similar to the purification method described above for the compound represented by formula A-5, this purification method allows for the efficient and large-scale production of high-quality oligosaccharides in the liquid-phase synthesis of oligosaccharide chains by using a small amount of hydrophobic support. In particular, compounds represented by formula A-8 as monosaccharides and compounds represented by formula A-9 as tetrasaccharides exhibit very similar polarities in cis-phase silicone column chromatography, for example, having the same Rf value under typical column solvent conditions of hexane-ethyl acetate, making separation difficult. However, by utilizing the purification method of this invention, monosaccharides and tetrasaccharides with very similar polarities can be easily separated. Furthermore, the purification of the compound represented by formula A-9 is not limited to the purification in step I-2-1. Therefore, in one embodiment of the present invention, a method is provided, comprising: adding a hydrophobic carrier and water to a water-soluble organic solvent containing the compound represented by formula A-9 and impurities, so that the compound represented by formula A-9 is adsorbed in the hydrophobic carrier, followed by filtration, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and water to remove impurities, and then using an organic solvent to dissolve the compound represented by formula A-9 from the hydrophobic carrier, thereby purifying the compound represented by formula A-9. The term "impurities" refers to compounds or reagents other than the protected oligosaccharide (the compound represented by formula A-9 in this step). It primarily refers to reagents used in the synthesis of the protected oligosaccharide or their residues, monosaccharide or disaccharide compounds used in the extension reaction of the protected oligosaccharide, or byproducts generated during the deprotection reaction of the protected oligosaccharide. Furthermore, the "hydrophobic support" (such as resin used in reverse-phase partition chromatography), "water-soluble organic solvent," "organic solvent," and purification temperature used in this step are the same as those described in the purification method for the compound represented by formula A-5 above. <Step I-2-2> Step I-2-2 is the step of generating the compound represented by formula A-9 from the compound represented by formula A-10. In one embodiment of the present invention, step I-2-2 involves reacting the compound represented by formula A-9 with a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid in a solvent, thereby removing the acetylation group (deacetylation reaction) to generate the compound represented by formula A-10. Preferably, this can be carried out using, for example, the method shown in Example 26. This deacetylation reaction, except for the different matrix, can be carried out in the same manner as the deacetylation reaction described in step X-7. By using the method of reacting a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid, the ring-opening of the phthalimide group can be suppressed, while the deacetylation reaction proceeds simultaneously. Furthermore, the aforementioned deacetylation reaction is not limited to its use in step I-2-2. Therefore, in one embodiment of the present invention, a method for manufacturing the compound represented by formula A-10 is provided, comprising the step of reacting the compound represented by formula A-9 with a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid. The alkyl esters of perfluorocarboxylic acids, strong bases, solvents, and reaction temperatures used in this step are as described in step X-7 above. <Step I-3> Step I-3 is the step of generating the oligosaccharide represented by formula A-13 above, which includes: generating the compound represented by formula A-12 below by forming a β-1,2-glycosidic bond between the compound represented by formula A-10 above and the compound represented by formula A-11 below. [Chemical 121] [Chemistry 122] In one embodiment of the present invention, step I-3 includes the following steps I-3-1 to I-3-2. <Step I-3-1> Step I-3-1 is the step of generating the compound represented by formula A-12 by forming a β-1,2-glycosidic bond between the compound represented by formula A-10 and the compound represented by formula A-11. The glycosidic bond formation step can be carried out using known methods, preferably by the method shown in Example 27. Furthermore, the compound represented by formula A-11 can be manufactured as follows. Subsequently, the compound represented by formula A-12 can be purified as follows. <Preparation of the Compound Represented by Formula A-11> In one embodiment, the compound represented by Formula A-11 is prepared by a step including the following steps: (Step Y-1) A step of generating the compound represented by Formula B-4, comprising: generating the compound represented by Formula B-3 by forming a β-1,4-glycosidic bond between the compound represented by Formula B-1 and the compound represented by Formula B-2; [Chemical 123] [Chemistry 124] [Chemistry 125] [Chemistry 126] (Step Y-2) This step involves adding lithium tributoxide or lithium tripentoxide to a solvent containing the compound represented by formula B-4 and a benzyl halide or benzyl sulfonate, thereby protecting the hydroxyl groups present in the compound represented by formula B-4 with the help of the benzyl group to generate the compound represented by formula B-5. [Chemistry 127] Step Y-1 above includes steps Y-1-1 and Y-1-2, and step Y-2 above includes steps Y-2-1 to Y-2-3. <Step Y-1-1> Step Y-1-1 is a step in which the compound represented by formula B-1 and the compound represented by formula B-2 are bonded together by a β1,4-glycosidic bond to generate the compound represented by formula B-3. A commercially available example of the compound represented by formula B-1 is 2,3,4,6-tetra-O-acetylated-α-D-galactopyranosyl-2,2,2-trichloroacetylatedimide ester (86520-63-0) manufactured by Tokyo Chemical Industries, Ltd. Another commercially available example of the compound represented by formula B-2 is 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimide-β-D-glucopyranoside manufactured by Tokyo Chemical Industries, Ltd. This step can be carried out by using or applying known methods, preferably by using, for example, the method shown in Example 3. For example, by sequentially adding a solution containing the compound represented by ... <Step Y-1-2> Step Y-1-2 is a step in which the acetyl group is removed from the compound represented by formula B-3 to generate the compound represented by formula B-4. [Chemistry 128] The deprotection of the acetyl group (AcO) can be carried out by known methods, preferably by methods such as those shown in Example 4. For example, the compound represented by formula B-3 can be reacted with a strong base in a solvent such as toluene in the presence of trifluoroacetate, causing the acetyl group to be removed and generating the compound represented by formula B-4. <Step Y-2-1> Step Y-2-1 is the step of generating the compound represented by formula B-5 by protecting the plurality of hydroxyl groups present in the compound represented by formula B-4 with benzyl groups. In one embodiment, step Y-2-1 is as follows: by adding lithium third butoxide or lithium third pentanol to a solvent containing the compound represented by formula B-4 and a benzyl halide (benzyl bromide, benzyl chloride, benzyl fluoride, or benzyl iodide) or benzyl sulfonate, the benzyl group protects the plurality of hydroxyl groups present in the compound represented by formula B-4, thereby generating the compound represented by formula B-5. When it is necessary to simultaneously benzylate the plurality of hydroxyl groups in a sugar derivative protected by the phthalimide group of the compound represented by B-4 (N-2) simultaneously, it is necessary to suppress the ring-opening of the phthalimide group while the reaction proceeds. However, the ring-opening reaction of phthalimide is easily carried out under strongly alkaline conditions due to the presence of trace amounts of hydroxide ions. Therefore, under the NaH / DMAc conditions used in previous benzylation reactions, the yield varies greatly depending on the amount of sodium hydroxide in the NaH, resulting in the disadvantage that NaH / DMAc is not suitable for large-scale synthesis due to the risk of mixing and explosion. The inventors have discovered a method that, by carrying out the above-mentioned benzylation reaction, can suppress the ring-opening of phthalimide and simultaneously benzylate multiple hydroxyl groups under milder conditions. Furthermore, the aforementioned benzylation reaction is not limited to its use in step Y-2-1. Therefore, in one embodiment of the present invention, a method for manufacturing the compound represented by formula B-5 is provided, comprising the following steps: adding lithium third butoxide or lithium third pentanoxide to a solution containing the compound represented by formula B-4 and a solvent containing a benzyl halide (benzyl bromide, benzyl chloride, benzyl fluoride, or benzyl iodide) or benzyl sulfonate, thereby protecting the hydroxyl groups present in the compound represented by formula B-4 using benzyl groups. The solvent used in this step is not particularly limited, as long as the reaction proceeds. Acetamide solvents (such as dimethylformamide and dimethylacetamide), ether solvents (such as tetrahydrofuran and dimethoxyethane), aromatic solvents (such as toluene), hydrocarbon solvents (such as hexane), urea solvents, or mixed solvents containing at least one of the above solvent systems can be used. Acetamide solvents (such as dimethylformamide and dimethylacetamide) are preferred. Furthermore, the reaction in this step is preferably carried out at 0°C to 60°C, and more preferably at 30°C to 50°C. <Purification of the Compound Represented by Formula B-5> The compound represented by Formula B-5 can be purified by the following steps. In this step, the phthalimide group in the compound represented by Formula B-5 is ring-opened, and then reacted with cinconidine to form a salt, thereby generating the following crystalline form of cinconidine salt, Formula B-6: [Chemistry 129] The compound represented by formula B-6, after separating the crystalline compound from the amorphous substance, is then treated with a solvent to remove cinconidine from the compound represented by formula B-6, yielding the following formula B-7: [Chemistry 130] The compound represented by formula B-7 is then subjected to ring closure of the aforementioned open-ring phthalimide group, thereby regenerating the compound represented by formula B-5. The compound represented by formula B-6 (the cinconidine salt of the compound represented by formula B-7) is crystalline. On the other hand, the compounds represented by formulas B-3, B-4, and B-5 are non-crystalline compounds. Therefore, the phthalimide in the compound represented by formula B-5 is temporarily ring-opened, and the carboxylic acid site in the generated phthalimide group forms a salt with cinconidine, thereby crystallizing the compound represented by formula B-5. After separating the crystalline substance from the non-crystalline substance, an acidic aqueous solution and solvent are added to remove the cinconidine in the compound represented by formula B-6, and then the phthalimide is ring-closed again, thereby obtaining a highly purified compound represented by formula B-5. Furthermore, the ring-opening and ring-closing of phthalimide can be carried out using known methods. For example, the ring-opening of phthalimide can be achieved by adding sodium hydroxide to methanol-tetrahydrofuran, and the ring-closing of phthalimide can be achieved by adding carbonyl diimidazole (CDI) to a tetrahydrofuran solvent. This step is preferably carried out using the methods shown in Examples 6 and 7, for example. <Step Y-2-2> Step Y-2-2 is a step in which the compound represented by formula B-5 is desorbed from a 4-methoxyphenyl compound to generate the compound represented by formula B-8. [Chemistry 131] In one embodiment, step Y-2-2 involves reacting the compound represented by formula B-5 with λ3-iodine in a fluorohydrin and water to remove 4-methoxyphenyl, thereby generating the compound represented by formula B-8. Preferably, this step can be carried out using, for example, the method shown in Example 8. This step can be performed according to step I-1-2 above, and the fluorohydrin and λ3-iodine used in this step can be the same as those used in step I-1-2 above. <Step Y-2-3> Step Y-2-3 is the step of generating the compound represented by formula B-8 from the compound represented by formula A-11. In one embodiment of the present invention, step Y-2-3 is the following step: reacting the compound represented by formula B-8 with 2,2,2-trifluoro-N-phenyliminoacetyl chloride (TFPC) in the presence of N-methylimidazole to generate the compound represented by formula A-11, preferably by the method shown in Example 9. As described with respect to the same reaction in step I-1-3, by using the above-mentioned N-methylimidazole as the base to be used, the equivalent of TFPC can be reduced compared with the case of using, for example, potassium carbonate, and the target product can be obtained in high yield. Furthermore, the solvent and reaction temperature used; it is also preferred to carry out the reaction in the presence of a dehydrating agent; and the separation and purification can be performed by column purification or the like, which are the same as in step I-1-3 above. <Purification of the Compound Represented by A-12> In step I-3-1 above, the purified form of the compound represented by formula A-12 can be obtained by the following purification method. This purification method includes: after terminating the reaction between the compound represented by formula A-10 and the compound represented by formula A-11, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by formula A-12 and impurities, causing the compound represented by formula A-12 to adsorb onto the hydrophobic carrier; then filtering; washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and water to remove impurities; and then using an organic solvent to dissolve the compound represented by formula A-12 from the hydrophobic carrier, thereby purifying the compound represented by formula A-12. Similarly to the purification method described in the above formula A-5, according to the above purification method, high-quality oligosaccharides can be produced in large quantities and efficiently in the liquid phase synthesis of oligosaccharide chains by using a small amount of hydrophobic carrier. Furthermore, the purification of the compound represented by formula A-12 is not limited to the purification in step I-3-1. Therefore, in one embodiment of the present invention, a method comprising the following steps is also provided: adding a hydrophobic carrier and water to a water-soluble organic solvent containing the compound represented by formula A-12 and impurities, so that the compound represented by formula A-12 is adsorbed into the hydrophobic carrier, followed by filtration, and washing the hydrophobic carrier with a mixed solution of the above-mentioned soluble organic solvent and water to remove impurities, and then using an organic solvent to dissolve the compound represented by formula A-12 from the hydrophobic carrier, thereby purifying the compound represented by formula A-12. The term "impurities" refers to compounds or reagents other than the protected oligosaccharide (the compound represented by formula A-12 in this step). It mainly refers to reagents or their residues used in the synthesis reaction of the protected oligosaccharide, monosaccharide or disaccharide compounds used in the extension reaction of the protected oligosaccharide, or byproducts generated by the deprotection reaction of the protected oligosaccharide. The "hydrophobic support" (such as resin used in reverse phase partition chromatography), "water-soluble organic solvent", "organic solvent", and purification temperature used in the above steps are the same as those described in the purification method for the compound represented by formula A-5 above. <Step I-3-2> Step I-3-2 is the step of generating an oligosaccharide represented by formula A-13 from the compound represented by formula A-12. In one embodiment of the present invention, step I-3-2 is a step of reacting the compound represented by formula A-12 with DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone) in a mixed solvent of fluoroalcohol and water to remove the 2-naphthylmethyl group in the compound represented by formula A-12 (de-naphthylmethylation reaction) and generate the oligosaccharide represented by formula A-13. It is preferred to carry out the step by, for example, the method shown in Example 28-1. Regarding the aforementioned de-2-naphthylmethylation reaction, the inventors have discovered that by reacting a matrix with a 2-naphthylmethyl group bonded via oxygen atoms in fluorohydrin and water with 2,3-dichloro-5,6-dicyano-p-benzoquinone, the reaction can be carried out under mild conditions with good stirring properties, and the de-2-naphthylmethylated product can be obtained in high yield. The advantages of this de-2-naphthylmethylation reaction will be further explained in detail below. In the aforementioned de-2-naphthylmethylation reaction of the present invention, the de-2-naphthylmethylated product can be obtained in high yield from a matrix such as a sugar with a 2-naphthylmethyl group bonded via oxygen atoms under mild conditions. No deterioration in stirring properties or adhesion to the container wall caused by 2,3-dichloro-5,6-dicyano-p-dihydroxybenzoquinone as a byproduct has been observed; the reaction can be carried out with good reproducibility and is also suitable for the large-scale synthesis of this product. Furthermore, due to HFIP-H The abnormal freezing point of 2O is lowered, so even when the reaction temperature is lowered to -30℃, solidification of the solvent is not confirmed. Based on the reactivity of the reaction matrix, a wider temperature range can be applied (melting point HFIP: -3.3℃, ​​H 2O: 0℃). It was also found that in the denaphthylmethylation reaction of compounds represented by formula A-12 containing multiple benzyl groups, using DDQ as an oxidant and HFIP-H... Using 2O as a solvent, the reaction proceeds with significantly better selectivity than under previous conditions. In several reported examples, a dichloromethane-aqueous bilayer reaction condition was used for this conversion reaction. In this case, the debenzylation of multiple benzyl groups proceeds at a moderate rate, with yields remaining at a moderate level. Although there are reported examples of improved conditions using β-pinene as an additive (see J. Org. Chem., 2017, 82, 3926, etc.), the yield remains at a moderate level for compounds with multiple Bn groups at multiple sites (see Angew. Chem. Int. Ed. 2021, 60, 19287, etc.). Furthermore, the selectivity for matrices with more than 10 benzyl groups at sites, as represented by formula A-12, is not fully understood. Moreover, the presence of DDQ and byproducts derived from DDQ in the dichloromethane-aqueous system leads to deterioration of stirring properties, making these reaction conditions unsuitable for large-scale synthesis. On the other hand, regarding the DDQ / HFIP-H of this law In the 2O series, compounds represented by formula A-12 with benzyl groups at 15 sites achieved high selectivity of over 85%. This method did not confirm the aforementioned deterioration in stirring properties derived from DDQ. Furthermore, due to HFIP-H The abnormally low freezing point of 2O meant that even when the reaction temperature was lowered to -30℃, solidification of the solvent was not confirmed. Based on the reactivity of the reaction matrix, a wide temperature range can be applied (melting point HFIP: -3.3℃, ​​H...). 2O: 0℃). Furthermore, the above-mentioned demethylation reaction of 2-naphthylmethylation is not limited to the reaction in step I-3-1. Therefore, in one embodiment of the present invention, a method for manufacturing the oligosaccharide represented by formula A-13 is also provided, which includes: reacting the compound represented by formula A-12 with DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone) in a mixed solvent of fluoroalcohol and water, thereby demethylating the 2-naphthylmethyl group in the compound represented by formula A-12. The "fluorinated alcohols" mentioned above are not limited, as long as the reaction proceeds. They are preferably selected from the group consisting of hexafluoro-2-propanol (HFIP), 2,2,2-trifluoroethanol (TFE), 2,2,3,3,4,4,5,5-octafluoro-1-pentanol, nonafluoro-tert-butanol, and combinations thereof. There are no limitations to the above-mentioned de-2-naphthylmethylation reaction, as long as the reaction proceeds. It is preferred to carry out the reaction at -35℃ to 70℃, and more preferably at -30℃ to -10℃. Using the above manufacturing method, the following formula A-13 is provided: [Chemical 132] The oligosaccharide represented by Formula A-13. The oligosaccharide represented by Formula A-13 also includes its variants, such as those with a benzyl chloride or similar protecting group replacing the benzyl group in the oligosaccharide represented by Formula A-13, as long as they have the same function or effect as the oligosaccharide. <Purification of the Compound Represented by Formula A-13> The compound represented by Formula A-13 can also be purified by the following steps. In this step, the phthalimide group in the compound represented by Formula A-13 is ring-opened, and then a salt is formed with (R)-(+)-1-(1-naphthyl)ethylamine, thereby generating a crystalline compound of the following formula A-14: [Chemistry 133] The compound represented by formula A-14 is obtained by separating the crystalline compound from the amorphous substance, and then adding an acidic aqueous solution and a solvent to remove (R)-(+)-1-(1-naphthyl)ethylamine from the compound represented by formula A-14, thereby generating the following formula A-15: [Chemistry 134] The compound represented by the formula A-15 is then used to circumcise the open-ring phthalimide group in the compound represented by the formula A-15, thereby regenerating the compound represented by the formula A-13. The compound represented by Formula A-14 (the (R)-(+)-1-(1-naphthyl)ethylamine salt of the compound represented by Formula A-15) is crystalline. On the other hand, the compound represented by Formula A-13 is an amorphous compound. Therefore, the phthalimide in the compound represented by Formula A-13 is temporarily ring-opened, and the carboxylic acid site in the phthalimide group formed thereby forms a salt with (R)-(+)-1-(1-naphthyl)ethylamine. After separating the crystalline and amorphous substances, an acidic aqueous solution and a solvent are added to remove the (R)-(+)-1-(1-naphthyl)ethylamine in the compound represented by Formula A-14, thereby obtaining the compound represented by Formula A-15. Then, the phthalimide is ring-closed again, thereby obtaining a highly purified compound represented by Formula A-13. Furthermore, the ring-opening and ring-closing of phthalimide can be carried out using known methods. For example, the ring-opening of phthalimide can be achieved by adding sodium hydroxide to methanol-tetrahydrofuran, and the ring-closing of phthalimide can be achieved by adding carbonyl diimidazole (CDI) to a tetrahydrofuran solvent. This step is preferably carried out using the method shown in, for example, Examples 28-2. <2. Method for Manufacturing Oligosaccharides Represented by Formula D-13> In one embodiment of the present invention, a novel oligosaccharide represented by formula D-13 and a novel method for manufacturing the same are provided. In the present invention, the oligosaccharide represented by formula D-13 refers to the following oligosaccharide. [Chemical 135] The novel synthetic process of the oligosaccharide represented by the above formula D-13 includes the following steps II-1 to II-4. <Step II-1> Step I-1 is the step of generating the compound represented by formula D-2, which includes: generating the compound represented by formula D-1 by forming an α-1,3-glycosidic bond between the oligosaccharide represented by formula A-13 and the compound represented by formula A-3. [Chemistry 136] [Chemistry 137] [Chemistry 138] [Chemistry 139] In one embodiment of the present invention, step II-1 includes the following steps II-1-1 to II-1-2. <Step II-1-1> Step II-1-1 is the step of producing the compound represented by formula D-1 by forming an α-1,3-glycosidic bond between the compound represented by formula A-13 and the compound represented by formula A-3. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 52, such as sequentially adding molecular sieve 4A powder and trimethylsilane trifluoromethanesulfonate (TMSOTf) to an organic solvent (toluene, etc.) to form an α-1,3-glycosidic bond between the compound represented by formula A-13 and the compound represented by formula A-3, thereby generating the compound represented by formula D-1. <Purification of the Compound Represented by Formula D-1> In step II-1-1, the compound represented by Formula D-1 can be obtained in its purified form by the following purification method. This purification method includes: after terminating the reaction between the compound represented by Formula A-13 and the compound represented by Formula A-3, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by Formula D-1 and impurities, causing the compound represented by Formula D-1 to adsorb onto the hydrophobic carrier; then filtering; washing the hydrophobic carrier with a mixture of the water-soluble organic solvent and water to remove impurities; and then using an organic solvent to dissolve the compound represented by Formula D-1 from the hydrophobic carrier, thereby purifying the compound represented by Formula D-1. Similar to the purification method for the compound represented by formula A-5 in step I-1-1 above, in this purification method, high-quality oligosaccharides can be produced in large quantities and efficiently in the liquid-phase synthesis of oligosaccharide chains by using a small amount of hydrophobic carrier. Furthermore, the purification of the compound represented by formula D-1 is not limited to the purification described in this step. Therefore, in one embodiment of the present invention, a method is also provided, comprising: adding a hydrophobic carrier and water to a water-soluble organic solvent containing the compound represented by formula D-1 and impurities, so that the compound represented by formula D-1 is adsorbed into the hydrophobic carrier, followed by filtration, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and water to remove impurities, and then using an organic solvent to dissolve the compound represented by formula D-1 from the hydrophobic carrier, thereby purifying the compound represented by formula D-1. The term "impurities" refers to compounds or reagents other than the protected oligosaccharide (represented by formula D-1 in this step). It primarily refers to reagents used in the synthesis of the protected oligosaccharide or their residues, monosaccharide or disaccharide compounds used in the extension reaction of the protected oligosaccharide, or byproducts generated during the deprotection reaction of the protected oligosaccharide. Furthermore, the "hydrophobic support" (such as resin used in reverse phase partition chromatography), "water-soluble organic solvent," "organic solvent," and purification temperature used in this step are the same as those described in the purification method for the compound represented by formula A-5 in step I-1-1 above. <Step II-1-2> Step II-1-2 is a step of generating the compound represented by formula D-2 by removing the acetyl group from the compound represented by formula D-1 above. This step can be carried out by using or applying known methods, but is preferably carried out by, for example, the method shown in Example 53. In one embodiment of the present invention, step II-1-2 involves reacting the compound represented by formula D-1 with a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid, thereby removing the acetylation group to generate the compound represented by formula D-2. This deacetylation reaction is carried out in the same manner as the deacetylation reaction described in step X-7, except for the different matrix. This method allows for the deacetylation reaction to be carried out simultaneously with the inhibition of ring-opening of the phthalimide group by utilizing the reaction with a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid. Furthermore, the aforementioned deacetylation reaction is not limited to its use in steps II-1-2. Therefore, in one embodiment of the present invention, a method for manufacturing the compound represented by formula D-2 is also provided, comprising the step of reacting the compound represented by formula D-1 with a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid. <Step II-2> Step II-2 is the following steps: generating a compound represented by formula D-5, wherein generating a compound represented by formula D-5 includes generating a compound represented by formula D-4 by forming a β-1,2-glycosidic bond between the compound represented by formula D-2 and the compound represented by formula D-3; after generating a compound represented by formula D-5, protecting the amino group in the compound represented by formula D-5 with a protecting group selected from aryloxycarbonyl (COOAr), acetyl (Ac), 2,2,2-trichloroethoxycarbonyl (Troc), and phthalimide (Pht) to generate formula D-6: [Chem. 140] [Chemistry 141] [Chemistry 142] [Chemistry 143] The compound represented (where R is a compound) 5 is an aryloxycarbonyl group (COOAr), acetyl (Ac), or 2,2,2-trichloroethoxycarbonyl (Troc), R 6 represents a hydrogen atom, or R 5 and R 6 together with the nitrogen atoms bonded thereto form a phthalimide group, or by removing the acetyl group (Ac) from the compound represented by formula D-4 above, to generate the compound represented by formula D-6 above (where R... 5 and R 6 together with the nitrogen atoms bonded thereto form phthalimide groups. In one embodiment of the present invention, step II-2 includes the following steps II-2-1 to II-2-3. <Step II-2-1> Step II-2-1 is the step of generating the compound represented by formula D-4 by forming a β-1,2-glycosidic bond between the compound represented by formula D-2 and the compound represented by formula D-3. The glycosidic bond formation step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 54, whereby the compound represented by formula D-2 is sequentially added to an organic solvent (such as toluene) with molecular sieve 4A powder and trimethylsilane trifluoromethanesulfonate (TMSOTf) to form a β-1,2-glycosidic bond with the compound represented by formula D-3, thereby generating the compound represented by formula D-4. <Preparation of the compound represented by formula D-3> The compound represented by formula D-3 can be prepared by the following steps Z-1 to Z-3. <Small Step Z-1> First, by using acetylene, we apply formula A-8, which is also used in step Y-1 above: [Chemistry 144] The hydroxyl groups on the represented compound are protected to form the following formula F-1: [Chemistry 145] The compound represented. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 34, which can be carried out by adding triethylamine, dimethylaminopyridine and acetic anhydride to an ethyl acetate solution of the compound represented by formula A-8, but is not limited to this method. <Small Step Z-2> Subsequently, by removing the compound represented by formula F-1 from 4-methoxyphenyl, the following formula F-2 is generated: [Chemistry 146] The compound represented. In one embodiment of the present invention, step Z-2 is a step of producing the compound represented by formula F-2 by reacting the compound represented by formula F-1 with λ3-iodine in fluoroalcohol and water to remove 4-methoxyphenyl. Preferably, this step can be carried out by, for example, the method shown in Example 35. This step can be performed according to steps I-1-2 above, and the fluoroalcohol and λ3-iodine used in this step can be the same as those used in steps I-1-2 above. <Sub-step Z-3> Sub-step Z-3 involves reacting the compound represented by formula F-2 with 2,2,2-trifluoro-N-phenyliminoacetyl chloride (TFPC) to produce formula D-3: [Chemistry 147] The steps for representing the compound. This step can be performed by using or applying known methods. In one embodiment of the present invention, step Z-3 involves reacting N-methylimidazole with 2,2,2-trifluoro-N-phenyliminoacetyl chloride (TFPC) to generate the compound represented by formula D-3 above. This step is preferably carried out by, for example, the method shown in Example 36. As described with respect to the same reaction in steps I-1-3, by using the aforementioned N-methylimidazole as the base, the equivalent amount of TFPC can be reduced compared to using, for example, potassium carbonate, thus obtaining the target compound in high yield. Furthermore, the solvent and reaction temperature used; and preferably, the reaction is carried out in the presence of a dehydrating agent; separation and purification can be performed by column purification or the like, just as in steps I-1-3 above. <Step II-2-2> Step II-2-2 is the step of removing the protecting group, i.e., the phthalimide group, of the amino group on the compound represented by formula D-4 to generate the compound represented by formula D-5. This step is preferably carried out by, for example, the method shown in Example 55-1, such as adding n-butanol and ethylenediamine to a solution containing the compound represented by formula D-4, but is not limited to them. <Purification of the compound represented by formula D-5 (1)> In step II-2-2, the compound represented by formula D-5 can be obtained in a purified form by the following purification method. The purification method includes: after terminating the reaction between the compound represented by formula D-3 and the compound represented by formula D-4, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by formula D-5 and impurities, so that the compound represented by formula D-5 is adsorbed into the hydrophobic carrier, followed by filtration, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and water to remove impurities, and then using an organic solvent to dissolve the compound represented by formula D-5 from the hydrophobic carrier, thereby purifying the compound represented by formula D-5. Similar to the purification method described in step I-1-1 above for the compound represented by formula A-5, this purification method can efficiently produce high-quality oligosaccharides in the liquid-phase synthesis of oligosaccharide chains by using a small amount of hydrophobic carrier. Furthermore, the purification of the compound represented by formula D-5 is not limited to the purification described in this step. Therefore, in one embodiment of the present invention, a method is also provided, comprising: adding a hydrophobic carrier and water to a water-soluble organic solvent containing the compound represented by formula D-5 and impurities, so that the compound represented by formula D-5 is adsorbed into the hydrophobic carrier, followed by filtration, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and water to remove impurities, and then using an organic solvent to dissolve the compound represented by formula D-5 from the hydrophobic carrier, thereby purifying the compound represented by formula D-5. The term "impurities" refers to compounds or reagents other than the protected oligosaccharide (represented by formula D-5 in this step). It primarily refers to reagents or their residues used in the synthesis of the protected oligosaccharide, monosaccharide or disaccharide compounds used in the extension reaction of the protected oligosaccharide, or byproducts generated during the deprotection reaction of the protected oligosaccharide. Furthermore, the "hydrophobic support" (such as resin used in reverse-phase partition chromatography), "water-soluble organic solvent," "organic solvent," and purification temperature used in this step are the same as those described in the purification method for the compound represented by formula A-5 in step I-1-1 above. <Purification of the compound represented by formula D-5 (2)> The compound represented by formula D-5 can also be purified by the following steps. Furthermore, this purification can be carried out separately from or together with the purification of the compound represented by formula D-5 (1). In this step, firstly, the compound represented by formula D-5 is reacted with fumaric acid, thereby generating the following crystalline form of fumaric acid salt, D-5-FMA: [Chem. 148] The compound represented by formula D-5-FMA is separated from the non-crystalline substance. The compound represented by formula D-5-FMA can be dissolved in a solvent and used directly in the following steps II-2-3, or it can be converted into the compound represented by formula D-5. The conversion to the compound represented by formula D-5 can be carried out by removing the fumaric acid in the compound represented by formula D-5-FMA in the aqueous layer by adding an alkaline aqueous solution and solvent, and then concentrating the organic layer, resulting in a highly purified compound represented by formula D-5. In this operation, stereoisomers and similar structural impurities that are difficult to remove even by column purification can also be easily removed. This step is preferably carried out by, for example, the method shown in Example 55-2. <Step II-2-3> Step II-2-3 is the following step: protecting the amine group in the compound represented by formula D-5 above with a protecting group selected from aryloxycarbonyl (COOAr), acetyl (Ac), 2,2,2-trichloroethoxycarbonyl (Troc), and phthalimide (Pht) to generate the compound represented by formula D-6 above (where R... 5 is an aryloxycarbonyl group (COOAr), an acetyl group (Ac), or a 2,2,2-trichloroethoxycarbonyl group (Troc), and R 6 represents a hydrogen atom, or R 5 and R 6. Together with the nitrogen atom it is bonded to, it forms a phthalimide group. The purpose of introducing the protecting group of the amine group as described above is that, in order to produce the target compound (the compound represented by formula D-13), the protecting group of the amine group is set to a more linear and efficient acetyl-based path. However, in the glycosylation reaction of the compound represented by formula D-6 and the compound represented by formula D-7 in the next step II-3, when the acetyl-protected amine group (-NHAc group) is present in the reaction matrix, it is observed that the reactivity of the target glycosylation reaction is significantly reduced due to the interaction with Lewis acid, thus requiring an excess of sugar donor to terminate the reaction. Therefore, during the above-mentioned glycosylation reaction, the nitrogen atom of glucosamine is protected by a protecting group selected from aryloxycarbonyl (COOAr), 2,2,2-trichloroethoxycarbonyl (Troc), and phthalimide (Pht) as a temporary protecting group. After the glycosylation reaction, deprotection occurs to form an -NHAc group, thereby avoiding the aforementioned unfavorable situation. Furthermore, aryloxycarbonyl (COOAr) is the most preferred protecting group. The term "aryl (Ar)" in aryloxycarbonyl refers to a group formed by removing one hydrogen atom from the aromatic ring of an aromatic hydrocarbon. It is not limited, but examples include: phenyl, 2-naphthyl, 1-naphthyl, 2-pyridyl, 3-pyridyl, nitrophenyl, chlorophenyl, fluorophenyl, bromophenyl, iodophenyl, methoxyphenyl, and C1-C4 alkylphenyl, with phenyl being preferred. It was found that the aryloxycarbonyl group (COOAr) facilitates glycosylation reactions more effectively than other protecting groups, and in the subsequent deprotection reaction, deprotection can be achieved under better conditions such as room temperature and within 1 hour under normal hydrolysis conditions. The above steps are preferably carried out by, for example, the methods shown in Examples 56 to 59. For example, they can be carried out by adding an aqueous solution of tetrahydrofuran and sodium bicarbonate, potassium bicarbonate, disodium hydrogen phosphate, or dipotassium hydrogen phosphate to a solution of the compound represented by formula D-5 in tetrahydrofuran, but are not limited to such methods. Instead of steps II-2-2 and II-2-3 above, the acetyl group (Ac) on the compound represented by formula D-4 above is selectively removed, thereby generating the compound represented by formula D-6 above (where R...). 5 and R 6. Together with the nitrogen atom to which it is bonded, it forms a phthalimide group. The selective removal of this acetyl group can be carried out under methyl trifluoroacetate conditions, but is not limited to this. This step yields the same result as in steps II-2-2 and II-2-3 where the phthalimide group (Pht) is selected as the protecting group for the amine group in the compound represented by formula D-5 above. <Step II-3> Step II-3 produces the compound represented by the following formula D-11 (where M... + The step (which involves sodium ions, lithium ions, potassium ions, or protonated triethylamine cations) includes the following step: reacting the compound represented by formula D-6 above with the following formula D-7: [Chemistry 149] The compound represented undergoes β-1,4-glycosidic bonding to form the following formula D-8: [Chemistry 150] The compound represented (where R is a compound) 5 is an aryloxycarbonyl group (COOAr), acetyl (Ac), or 2,2,2-trichloroethoxycarbonyl (Troc), R 6 represents a hydrogen atom, or R 5 and R 6, together with the nitrogen atom it is bonded to, forms a phthalimide group, and then the protecting group of the amine group in the compound represented by formula D-8 is removed to generate the following formula D-9: [Chemical 151] The compound represented (where M is a compound) + (Sodium ion, lithium ion, potassium ion, or protonated triethylamine cation) [Chemistry 152] In one embodiment of the present invention, step II-3 includes the following steps II-3-1 to II-3-4. <Step II-3-1> This step involves forming a β-1,4-glycosidic bond between the compound represented by formula D-6 and the compound represented by formula D-7 to generate the compound represented by formula D-8. The glycosidic bond formation step can be carried out using known methods, but is preferably carried out using methods such as those shown in Examples 60-63. <Preparation of the Compound Represented by Formula D-7> In one embodiment of the present invention, the compound represented by Formula D-7 can be prepared by the following steps V-1 to V-11. Step V-7, which involves forming a disaccharide block by α-2,6-glycosidic bonding between two monosaccharide molecules, is a necessary step. Otherwise, it can be carried out using conventional methods in the manufacture of monosaccharides or oligosaccharides, or by applying such conventional methods. In one embodiment of the present invention, step V includes the following sub-steps. [Chemical 153] <Sub-step V-1> Sub-step V-1 is performed by using a benzoyl group to form the following formula G-1: [Chemistry 154] The hydroxyl groups on the compound represented are protected to produce the following formula G-2: [Chemistry 155] The steps involving the compound represented by the compound. The compound represented by formula G-1, which serves as the starting material for this step, is specifically the compound with CAS number 100759-10-2, and can be manufactured by known methods, for example, by the methods shown in Examples 37 and 38. This step can be carried out by utilizing or applying known methods, preferably by, for example, the method shown in Example 39. <Sub-step V-2> Sub-step V-2 is performed by removing the benzylidene protecting group from the compound represented by formula G-2 to produce the following formula G-3: [Chemistry 156] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 40. In one embodiment of the present invention, this step includes the following step: solid-phase extraction of the compound represented by formula G-3 by contacting the solvent in which the dissolved compound G-3 is generated with silicone. Since the unreacted compound represented by formula G-2, or the detached benzaldehyde, will not be adsorbed onto the silicone, the compound represented by formula G-3 can be purified efficiently through this step. Examples of solvents for dissolving compounds represented by formula G-3 include toluene, heptane, dichloromethane, chloroform, or combinations thereof, with toluene, dichloromethane, chloroform, or combinations thereof being preferred, and toluene being particularly preferred, but not limited to these. The silicone used in this step can be, for example, in amounts of 2 to 5 times that of the raw material, preferably in amounts of 2 to 4 times that of the raw material, and even more preferably in amounts of about 3 times that of the raw material. In this step, the solvent used to dissolve the compound represented by formula G-3 adsorbed on the silicone is not particularly limited as long as it is a solvent that can dissolve the target substance without dissolving the silicone. Examples include cyclopentyl methyl ether, ethyl acetate, or tributyl methyl ether. <Minor Step V-3> Minor step V-3 is achieved by making the following equation G-4: [Chemistry 157] The carboxylic acid esterification of the represented compound, followed by the addition of water, produces the following formula G-5: [Chemistry 158] The steps involving the compound represented by formula G-4. The compound represented by formula G-4, which serves as the starting material for this step, can be manufactured using known methods or can be a commercially available product. For example, N-acetylglucosamine acid manufactured by Tokyo Chemical Industries can be cited as a commercially available product of formula G-4. This step can be carried out using or applying known methods, but is preferably carried out using, for example, the method shown in Example 41. <Sub-step V-4> Sub-step V-4 involves selectively protecting a hydroxyl group other than the hydroxyl group bonded to the carbon at position 1 in the compound represented by formula G-5 using an acetyl group, thereby producing the following formula G-6: [Chemistry 159] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 42. <Sub-step V-5> Sub-step V-5 involves reacting the compound represented by formula G-6 with 2,2,2-trifluoro-N-phenyliminoacetyl chloride (TFPC) to produce the following formula G-7: [Chemistry 160] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 43. In one embodiment of the present invention, this step involves reacting the compound represented by formula G-6 with TFPC in the presence of N-methylimidazole to produce the compound represented by formula G-7. Regarding the base used in this step, and the use of K... 2CO Compared to scenario 3, when using N-methylimidazole, the equivalent of TFPC can be reduced, and the target compound can still be obtained in high yield. TFPC is a high-value reagent, therefore, the yield improvement in this step is highly advantageous for commercial production. There are no restrictions on the solvent used in this step, as long as the reaction proceeds. Examples of solvents include dichloromethane, toluene, ethyl acetate, acetonitrile, or tetrahydrofuran, with dichloromethane being a preferred choice. There is no limit to the reaction temperature in this step, as long as the reaction proceeds. Preferably, it is 20℃~40℃, more preferably 10℃~35℃, and even more preferably 0℃~30℃. This step is preferably carried out in the presence of a dehydrating agent. There are no restrictions on the dehydrating agent used in this step, as long as the reaction proceeds. For example, molecular sieves can be used, and preferably, molecular sieve 4A powder with a particle size of less than 10 μm can be used. <Sub-step V-6> Sub-step V-6 involves using a tert-butoxycarbonyl group to protect the nitrogen atom in the acetaminophen group of the compound represented by formula G-7 to produce the following formula G-8: [Chemistry 161] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 44. In this step, the compound represented by formula G-8 can be dissolved in a solvent and used directly in the next step, or it can be isolated and purified by recrystallization. A major advantage of the compound represented by formula G-8 is that it can be isolated and purified by crystallization. Crystallization yields a compound represented by formula G-8 with an HPLC purity of over 99%. Because it is free of impurities, it can stably carry out the glycosylation reaction in the next step. Isolation and purification using recrystallization can be carried out, for example, by adding heptane to a solution of cyclopentyl methyl ether for crystallization. <Minor Step V-7> Minor step V-7 involves creating formula G-9 by forming an α-2,6-glycosidic bond between the compound represented by formula G-8 and the compound represented by formula G-3: [Chemistry 162] The steps for reacting the N-acetylglucosamine derivative with the galactose derivative to selectively form an α-2,6-glycosidic bond are quite difficult. For example, a method for synthesizing disaccharides by reacting the compound represented by formula G-7 with the compound represented by formula G-3 has been reported (J. Org. Chem., 2016, 81, 10600-10616). However, the reproducibility of this reaction is not easy, and the desired yield and selectivity cannot be obtained. Furthermore, the following issues exist with this reaction: the selectivity decreases with increasing scale, the allowable reaction temperature range narrows, and the influence of the heat of reaction is significant. Because the compound represented by formula G-7, one of the starting materials for this reaction, is of very high value, the low reproducibility, yield, and selectivity of this reaction pose significant problems, especially for commercial production requiring scale-up. On the other hand, if the compound represented by formula G-8, which has a tert-butoxycarbonyl group, is used instead of the compound represented by formula G-7 as the starting material, the reproducibility is excellent, achieving high selectivity for α-2,6-glycosidic bonds (α:β = 93:7), and the yield is also improved. Furthermore, the temperature tolerance range is widened, and high reproducibility, high yield, and high selectivity can be achieved during scale-up. This brings extremely beneficial effects to commercial production. This step can preferably be carried out in the presence of a Lewis acid. There are no limitations on the Lewis acid used in this step, as long as the reaction proceeds. Examples include trimethylsilane trifluoromethanesulfonate, triisopropylsilane trifluoromethanesulfonate, and tributyldimethylsilane trifluoromethanesulfonate; trimethylsilane trifluoromethanesulfonate is a preferred example. There are no restrictions on the solvent used in this step, as long as the reaction proceeds. Examples of solvents include diisopropyl ether, tributylmethyl ether, diethyl ether, dibutyl ether, dipropyl ether, 1,4-dimethyl ether, dichloromethane, 1,2-dichloroethane, toluene, chlorobenzene, trifluoromethylbenzene, propionitrile, or acetonitrile. Cyclopentyl methyl ether is a preferred example. There is no limitation on the reaction temperature in this step, as long as the reaction proceeds. For example, -78℃ to 0℃ is acceptable, -78℃ to -20℃ is preferable, -78℃ to -30℃ is even better, and -78℃ to -40℃ is particularly desirable. In this step, it is preferable to add 1 to 3 equivalents of the compound represented by formula G-3 relative to 1 equivalent of the compound represented by formula G-8, and more preferably to add 1.4 to 2 equivalents of the compound represented by formula G-3 relative to 1 equivalent of the compound represented by formula G-8. This step is not limited, as long as the reaction proceeds. For example, it can be carried out by adding a mixed solution of the compound represented by formula G-8 and the compound represented by formula G-3 (preferably a cyclopentyl methyl ether mixed solution) dropwise over a long period of time to a solution containing a Lewis acid (preferably a cyclopentyl methyl ether solution), or by adding a solution of the compound represented by formula G-8 (preferably a cyclopentyl methyl ether solution) dropwise over a long period of time to a solution containing a Lewis acid and the compound represented by formula G-3 (preferably a cyclopentyl methyl ether solution). It is more preferably carried out by adding a solution of the compound represented by formula G-8 (preferably a cyclopentyl methyl ether solution) dropwise over a long period of time to a solution containing a Lewis acid and the compound represented by formula G-3 (preferably a cyclopentyl methyl ether solution). The dropping time is not limited, as long as the reaction proceeds, for example, 30 minutes to 5 hours, preferably 1 hour to 4 hours, more preferably 2 hours to 3.5 hours, and most preferably about 3 hours. In one embodiment of the present invention, this step includes the following steps: solid-phase extraction of the compound represented by formula G-9 by contacting a solvent containing the dissolved compound with silicone. Since the N-phenyltrifluoroacetamide byproduct generated during the glycosylation reaction and other trace impurities in the toluene solvent that are not adsorbed onto the silicone are not adsorbed onto the silicone, this step can efficiently purify the compound represented by formula G-9. Examples of solvents for dissolving compounds represented by formula G-9 include toluene, heptane, dichloromethane, chloroform, or combinations thereof, with toluene, dichloromethane, chloroform, or combinations thereof being preferred, and toluene being particularly preferred, but not limited to these. The silicone used in this step can be, for example, in an amount of 2 to 5 times that of the raw material, preferably in an amount of 2 to 4 times that of the raw material, and even more preferably in an amount of about 3.5 times that of the raw material. In this step, the solvent used to dissolve the compound represented by formula G-9 adsorbed on the silicone is not particularly limited as long as it is a solvent that will not dissolve the silicone but can dissolve the target substance. Examples include ethyl acetate, cyclopentyl methyl ether, or tributyl methyl ether, with ethyl acetate being a preferred example. This step can be performed, for example, by the method shown in Example 45. <Sub-step V-8> Sub-step V-8 involves removing the tert-butoxycarbonyl group from the compound represented by formula G-9 to produce the following formula G-10: [Chemistry 163] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 46. <Minor Step V-9> Minor step V-9 involves further protecting the hydroxyl group of the compound represented by formula G-10 with an acetyl group, and the nitrogen atom in the acetamino group, to produce the following formula G-11: [Chemistry 164] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 47. In one embodiment of the present invention, this step includes the following step: a solid-phase extraction step of the compound represented by formula G-11 by contacting a solvent containing the dissolved compound G-11 with silicone. Since the byproducts such as the diacetyl matrix of the compound represented by formula G-3, which are generated by the acetylation of the compound used in excess in the upstream glycosylation reaction, do not adsorb onto the silicone, this step allows for efficient purification of the compound represented by formula G-11. Examples of solvents used to dissolve compounds represented by formula G-11 include toluene, heptane, dichloromethane, chloroform, or combinations thereof, with toluene, dichloromethane, chloroform, or combinations thereof being preferred, and toluene being particularly preferred, but not limited to these. The silicone used in this step can be, for example, in an amount of 2 to 5 times that of the raw material, preferably in an amount of 2 to 4 times that of the raw material, and even more preferably in an amount of about 3.5 times that of the raw material. In this step, the solvent used to dissolve the compound represented by formula G-11 adsorbed on the silicone is not particularly limited as long as it is a solvent that will not dissolve the silicone but can dissolve the target substance. Examples include ethyl acetate, cyclopentyl methyl ether, or tributyl methyl ether, with ethyl acetate being a preferred example. <Sub-step V-10> Sub-step V-10 is performed by removing the allyl group bonded to the 1-carbon of the D-galactofuranyl glycoside in the compound represented by formula G-11, to produce the following formula G-12: [Chemistry 165] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 48. In this step, the compound represented by formula G-12 can be dissolved in a solvent and used directly in the next step, or it can be isolated and purified by recrystallization. A major advantage of the compound represented by formula G-12 is that it can be isolated and purified by crystallization. Crystallization yields a compound represented by formula G-12 with an HPLC purity of 99% or higher. Because it is free of impurities, the reaction in the next step can be carried out stably. Isolation and purification by recrystallization can be carried out, for example, by adding 2-propanol to a solution of ethyl acetate containing the compound represented by formula G-12 for crystallization, and preferably by the method shown in Example 48. <Minor Step V-11> Minor step V-11 involves reacting the compound represented by formula G-12 with 2,2,2-trifluoro-N-phenyliminoacetyl chloride (TFPC) to produce the following formula D-7: [Chemistry 166] The steps for representing the compound. This step can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 49. <Purification of the Compound Represented by Formula D-8> In step II-3-1, the compound represented by formula D-8 can be purified by the following purification method. This purification method includes: after terminating the reaction between the compound represented by formula D-6 and the compound represented by formula D-7, adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by formula D-8 and impurities, causing the compound represented by formula D-8 to adsorb onto the hydrophobic carrier; then filtering; washing the hydrophobic carrier with a mixture of the water-soluble organic solvent and water to remove impurities; and then using an organic solvent to dissolve the compound represented by formula D-8 from the hydrophobic carrier, thereby purifying the compound represented by formula D-8. Similar to the purification method described in step I-1-1 above for the compound represented by formula A-5, this purification method can efficiently produce high-quality oligosaccharides in the liquid-phase synthesis of oligosaccharide chains by using a small amount of hydrophobic carrier. Furthermore, the purification of the compound represented by formula D-8 is not limited to the purification described in this step. Therefore, in one embodiment of the present invention, a method is also provided, comprising: adding a hydrophobic carrier and water to a water-soluble organic solvent containing the compound represented by formula D-8 and impurities, so that the compound represented by formula D-8 is adsorbed in the hydrophobic carrier, followed by filtration, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and water to remove impurities, and then using an organic solvent to dissolve the compound represented by formula D-8 from the hydrophobic carrier, thereby purifying the compound represented by formula D-8. The term "impurities" refers to compounds or reagents other than the protected oligosaccharide (the compound represented by formula D-8 in this step). It primarily refers to reagents used in the synthesis of the protected oligosaccharide or their residues, monosaccharide or disaccharide compounds used in the extension reaction of the protected oligosaccharide, or byproducts generated during the deprotection reaction of the protected oligosaccharide. Furthermore, the "hydrophobic support" (such as resin used in reverse phase partition chromatography), "water-soluble organic solvent," "organic solvent," and purification temperature used in this step are the same as those described in the purification method for the compound represented by formula A-5 in step I-1-1 above. <Step II-3-2> This step involves removing the protecting groups of the amine group and the acetylated protecting groups of the alcohol from the compound represented by formula D-8 to generate the compound represented by formula D-9. The removal (deprotection) of the amine group can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 64, such as by sequentially adding 1,2-dimethoxyethane and aqueous solutions of potassium hydroxide, sodium hydroxide, or lithium hydroxide, but is not limited to these methods. The following steps II-3-3 to II-3-4 are exemplary embodiments for manufacturing compounds represented by formula D-9 and D-11, but are not limited to these manufacturing steps. <Step II-3-3> This step involves protecting the amino group on the compound represented by formula D-9 with an acetyl group to generate the following formula D-10: [Chemistry 167] The steps for the compound represented. The protection of the acetyl amine group described above can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 65. <Purification of the Compound Represented by Formula D-10> In step II-3-3, the compound represented by formula D-10 can be obtained in a purified state by the following purification method. This purification method includes: adding a hydrophobic carrier and water to a water-soluble organic solvent containing the generated compound represented by formula D-10 and impurities, causing the compound represented by formula D-10 to adsorb onto the hydrophobic carrier; then filtering; washing the hydrophobic carrier with a mixture of the water-soluble organic solvent and water to remove impurities; and then using an organic solvent to dissolve the compound represented by formula D-10 from the hydrophobic carrier, thereby purifying the compound represented by formula D-10. Similar to the purification method for the compound represented by formula A-5 in step I-1-1 above, this purification method allows for the efficient and large-scale production of high-quality oligosaccharides in the liquid-phase synthesis of oligosaccharide chains using a small amount of hydrophobic carrier. Furthermore, the purification of the compound represented by formula D-10 is not limited to the purification described in this step. Therefore, in one embodiment of the present invention, a method is also provided, comprising: adding a hydrophobic carrier and water to a water-soluble organic solvent containing the compound represented by formula D-10 and impurities, so that the compound represented by formula D-10 is adsorbed into the hydrophobic carrier, followed by filtration, and washing the hydrophobic carrier with a mixed solution of the water-soluble organic solvent and water to remove impurities, and then using an organic solvent to dissolve the compound represented by formula D-10 from the hydrophobic carrier, thereby purifying the compound represented by formula D-10. The term "impurities" refers to compounds or reagents other than the protected oligosaccharide (in this step, the compound represented by formula D-10). It primarily refers to reagents used in the synthesis of the protected oligosaccharide or their residues, monosaccharide or disaccharide compounds used in the extension reaction of the protected oligosaccharide, or byproducts generated during the deprotection reaction of the protected oligosaccharide. Furthermore, the "hydrophobic support" (such as resin used in reverse phase partition chromatography), "water-soluble organic solvent," "organic solvent," and purification temperature used in this step are the same as those described in the purification method for the compound represented by formula A-5 in step I-1-1 above. <Step II-3-4> This step involves removing the benzyl group from the benzyloxy group on the compound represented by formula D-10 to generate the compound represented by formula D-11. The removal of the benzyl group can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 66. For example, it can be carried out by adding N-methylpyrrolidone and Pd / C to the compound represented by formula D-10 and performing depressurization → nitrogen replacement and hydrogen pressurization → depressurization, but is not limited to these methods. <Step II-4> Step II-4 comprises the following steps: by reacting the compound represented by formula D-11 above with the following formula D-12 as an azide PEG linker: [Chemistry 168] The compound represented (11-azido-3,6,9-trioxaundecan-1-amine) reacts to generate the oligosaccharide represented by formula D-13 above. The bond between the compound represented by formula D-11 and the compound represented by formula D-12 can be carried out by using or applying known methods, preferably by, for example, the method shown in Example 72. For example, it can be carried out by sequentially adding the compound represented by formula D-12, N-ethyldiisopropylamine, and hexafluorophosphate (benzotriazol-1-yloxy)tripyrrolylphosphonium, bromotripyrrolylphosphonium=hexafluorophosphate, or 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholine hydrochloride to a solution containing the compound represented by formula D-11, followed by stirring, but is not limited to these methods. <Purification of the Compound Represented by Formula D-12> In one embodiment of the present invention, the compound represented by Formula D-12 is obtained by a purification method comprising the following steps: adding the following formula E-1 to a solution containing the crude compound represented by Formula D-12: [Chemical 169] The compound represented (where R is a compound) 7 is a hydrogen atom, a methyl group, or a methoxy group, and it produces the following formula E-2: [Chemistry 170] The crystalline compound represented (where R is a crystalline compound) The purification process includes steps 7 (where 7 represents hydrogen atoms, methyl groups, or methoxy groups); and isolating the crystalline compound and then extracting the compound represented by formula D-12 from the isolated crystalline compound. This purification method yields a compound represented by formula D-12 with a high purity, where the purity (also referred to as "HPLC purity" in this specification) is preferably 95% or higher, more preferably 96% or higher, or 97% or higher, and even more preferably 98% or higher, or 99% or higher. As mentioned above, the reason for purifying the compound represented by D-12 is that commercially available reagents containing this compound contain various impurities, such as dimers. Furthermore, in the prior art, such purification requires rigorous distillation or complex column purification. In cases involving azide structures, there are concerns about explosion, making it unsuitable for distillation operations requiring heating. The inventors investigated a purification method for obtaining compounds represented by formula D-12 with high purity, and found that using the three tartaric acid derivatives shown in formula E-1 (where R...)... When 7 is a hydrogen atom, methyl group, or methoxy group, the compound represented by formula D-12 forms a 1:1 salt with these tartaric acid derivatives and can be isolated in crystalline form. The obtained compound represented by formula E-2 is a novel crystalline compound. After isolation, it is separated by liquid-liquid extraction using ethyl acetate / hydrochloric acid aqueous solution, followed by ionization and extraction, thereby obtaining the compound represented by formula D-12 with a higher HPLC purity (preferably 95% or higher) than before purification. An example of the purification method described above is as follows. First, the compound represented by formula E-1 is added to a solution of the compound represented by formula D-12 in solvents such as acetonitrile and water. The mixture is stirred until dissolved, and then acetonitrile or other solvents are added. The resulting slurry is concentrated under reduced pressure, and the slurry is stirred while filtering to obtain the precipitated crystals. The filtered crystals are washed with acetonitrile and dried under reduced pressure to obtain crystals of the compound represented by formula E-2 (crystallization step). Next, concentrated hydrochloric acid is added to a solution of the obtained crystalline compound in ethyl acetate and water. After stirring, the mixture is separated into layers. The aqueous layer is washed with ethyl acetate or the like, and the solution is adjusted to alkalinity using an aqueous sodium hydroxide solution or the like. Sodium chloride or the like is then added to dissolve the aqueous layer. A solvent such as dichloromethane is added, and the mixture is stirred while separating into layers. The resulting organic layer is concentrated under reduced pressure. After adding solvents such as acetonitrile and concentrating under reduced pressure, the resulting solution is filtered, washed with solvents such as acetonitrile, and then concentrated under reduced pressure (extraction step) to obtain the compound represented by formula D-12 with high purity according to HPLC. Preferably, this can be carried out by, for example, the method shown in Examples 67-71. Furthermore, the purification of the compound represented by formula D-12 is not limited to the purification in this step. Therefore, in one embodiment of the present invention, a method for purifying the compound represented by formula D-12 is also provided, which includes: adding the compound represented by formula E-1 (where R) to a solution containing crude compound represented by formula D-12. 7 represents a hydrogen atom, a methyl group, or a methoxy group, and thus forms a crystalline compound represented by the above formula E-2 (where R is a hydrogen atom, a methyl group, or a methoxy group). The steps are: 7) for hydrogen atoms, methyl groups, or methoxy groups; and 8) for isolating the crystalline compound and then extracting the compound represented by formula D-12 from the isolated crystalline compound. <Novel Compound> The intermediate of the oligosaccharide represented by Formula A-13 above can be used to manufacture the oligosaccharide, but is not limited to the manufacture of the oligosaccharide and is applicable to all uses. Therefore, by means of the present invention, an oligosaccharide represented by Formula A-13 above and its intermediates are provided. In one embodiment of the present invention, an oligosaccharide represented by the following formula A-13 is provided. [Chemical 171] In one embodiment of the present invention, compounds represented by formulas A-5 are provided. [Chemical 172] In one embodiment of the present invention, compounds represented by formulas A-6 are provided. [Chemical 173] In one embodiment of the present invention, compounds represented by formulas A-7 are provided. [Chemical 174] In one embodiment of the present invention, compounds represented by formulas A-9 are provided. [Chemical 175] In one embodiment of the present invention, compounds represented by formulas A-10 are provided. [Chemical 176] In one embodiment of the present invention, a compound represented by the following formula A-11 is provided. [Chemical 177] In one embodiment of the present invention, a compound represented by the following formula A-12 is provided. [Chemical 178] In one embodiment of the present invention, a compound represented by the following formula A-14 is provided. [Chemical 179] In one embodiment of the present invention, a compound represented by the following formula A-15 is provided. [Chemical 180] Furthermore, the intermediate of the compound represented by formula A-11 above can be used to manufacture the compound, but is not limited to the manufacture of the compound and is applicable to all uses. Therefore, by means of the present invention, an intermediate of the compound represented by formula A-11 above is also provided. In one embodiment of the present invention, a compound represented by formula B-4 is provided. [Chemical 181] In one embodiment of the present invention, a compound represented by formula B-5 is provided. [Chemical 182] In one embodiment of the present invention, a compound represented by formula B-6 is provided. [Chemical 183] In one embodiment of the present invention, a compound represented by formula B-7 is provided. [Chemical 184] In one embodiment of the present invention, compounds represented by formulas B-8 are provided. [Chemical 185] Furthermore, the intermediate of the oligosaccharide represented by formula D-13 above can be used in the manufacture of the oligosaccharide, but is not limited to the manufacture of the oligosaccharide, and is applicable to all uses. As shown below, by means of the present invention, oligosaccharides represented by formula D-13 above and their intermediates (including compounds represented by formula A-13 above and their intermediates) are provided. In one embodiment of the present invention, an oligosaccharide represented by formula D-13 is provided. [Chemical 186] In one embodiment of the present invention, a compound represented by the following formula D-1 is provided. [Chemical 187] Provide the compound represented by the following formula D-2. [Chemistry 188] In one embodiment of the present invention, a compound represented by formula D-4 is provided. [Chemical 189] In one embodiment of the present invention, a compound represented by formula D-5 is provided. [Chemical 190] In one embodiment of the present invention, a compound represented by the formula D-5-FMA is provided. [Chemical 191] In one embodiment of the present invention, a compound represented by formula D-6 is provided. [Chemical 192] (where R is in the formula) 5 is an aryloxycarbonyl group (COOAr), acetyl (Ac), or 2,2,2-trichloroethoxycarbonyl (Troc), R 6 represents a hydrogen atom, or R 5 and R 6, together with the nitrogen atoms it bonds to, forms an orthophthalimide group. In one embodiment of the present invention, a compound represented by formula D-8 is provided. [Chemical 193] (where R is in the formula) 5 is an aryloxycarbonyl group (COOAr), acetyl (Ac), or 2,2,2-trichloroethoxycarbonyl (Troc), R 6 represents a hydrogen atom, or R 5 and R 6, together with the nitrogen atoms it bonds to, forms an orthophthalimide group. In one embodiment of the present invention, a compound represented by formula D-9 is provided. [Chemical 194] (where M is in the formula) + (These are sodium ions, lithium ions, potassium ions, or protonated triethylamine cations). In one embodiment of the present invention, a compound represented by the following formula D-10 is provided. [Chemical 195] (where M is in the formula) + (These are sodium ions, lithium ions, potassium ions, or protonated triethylamine cations). In one embodiment of the present invention, a compound represented by the following formula D-11 is provided. [Chemical 196] (where M is in the formula) + (These are sodium ions, lithium ions, potassium ions, or protonated triethylamine cations). In one embodiment of the present invention, a crystalline compound represented by the following formula E-2 is provided. [Chemical 197] (where R is in the formula) 7 represents a hydrogen atom, a methyl group, or a methoxy group. In one embodiment of the present invention, a compound represented by formula D-12 is provided, which has a purity of 95% or higher when determined by HPLC. [Chemical 198] In one embodiment of the present invention, a compound represented by the above formula D-12 is provided, which has a purity of 95% or higher when determined by HPLC. <Glycoproteins, etc., and methods for their manufacture> In one aspect of the present invention, a novel glycoprotein, etc., is provided, and a novel method for its manufacture is provided, utilizing a bibranched polysaccharide (i.e., an oligosaccharide represented by formula D-13) having an α2,6-sialic acid structure at its non-reducing end as a donor molecule for the synthesis of glycoproteins, etc. (especially glycan remodeling antibodies or molecules containing their Fc regions, or antibody-drug conjugates). As detailed below, the oligosaccharide represented by formula D-13 obtained by the manufacturing method of the present invention can be used to manufacture glycoproteins (especially glycan remodeling antibodies or molecules containing Fc regions, or antibody-drug conjugates) (WO2019 / 065964, WO2020 / 050406, etc.), but is not limited thereto, and can also be used for other purposes. In recent years, methods have been reported for remodeling heterogeneous antibody glycans via enzymatic reactions to uniformly introduce functional glycans (ACS Chem. Biol. 2012, 7, 110-122, ACS Med. Chem. Lett. 2016, 7, 1005-1008). This glycan remodeling technique has been used to site-specifically deliver drugs, synthesizing homogeneous antibody-drug conjugates (ADCs) (Bioconjugate Chem. 2015, 26, 2233-2242, Angew. Chem. Int. Ed. 2016, 55, 2361-2367, US2016361436). In glycan remodeling, a hydrolase is first used to remove only the terminal N-acetylglucosamine (GlcNAc) residue from the heterogeneous glycan attached to the protein (antibody, etc.), thus preparing a homogeneous protein moiety with attached GlcNAc (hereinafter referred to as the "receptor molecule"). Next, a separately prepared arbitrary glycan (hereinafter referred to as the "donor molecule") is prepared, and the receptor molecule and the donor molecule are linked using a glycosyltransferase. In this way, a homogeneous glycoprotein with an arbitrary glycan structure can be synthesized. In one embodiment of the present invention, the oligosaccharide represented by formula D-13, manufactured using the novel manufacturing method of the present invention, can be used as a donor molecule for the synthesis of the aforementioned homogeneous glycoproteins (especially glycan remodeling antibodies or molecules containing their Fc regions) by activating its terminal structure. [Example] In the following examples, room temperature ranges from 15°C to 35°C. Silicone chromatography was performed using a Biotage Sfar HC D (20 μm, manufactured by Biotage), reverse-phase column chromatography used Universal Column ODS Premium 30 μm L-size (manufactured by Yamazen Corporation) and Inject column ODS L-size (manufactured by Yamazen Corporation), and fractional HPLC was performed using an Agilent Preparative HPLC System (manufactured by Agilent Technology). The fractional column used was an XBridge Prep OBD (5 μm, C18, 130 Å, 250 × 30 mm, manufactured by Waters). The following machines are used for measuring various spectral data. 1 H-NMR and 13 C-NMR spectra were determined using JEOL ECZ500R and ECX400P. Mass spectra were determined using Shimadzu LCMS-2010 and LCMS-2020 (manufactured by Shimadzu Corporation), XEVO Q-Tof MS (Waters), and Q-Exactive (Thermo Fisher). <Synthesis of the Compound Represented by Formula A-3> The compound represented by formula A-3 was synthesized according to the following synthetic procedure 1. [Synthetic Procedure 1] [Chemistry 199] Example 1: 2-O-acetylated-3,4,6-tris-O-benzyl-D-mannose (compound represented by formula A-2) [Chemical 200] 40.0 g (78.9 mmol) of 3,4,6-tris-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannose (the compound represented by formula A-1) was added to a 1 L 4-inch flask, followed by the addition of ethyl acetate (400 mL). Water (2 mL) and hydroxylamine (TsOH·H₂O) were then added at room temperature under a nitrogen atmosphere. 2O (45 mg, 0.237 mmol) was added and stirred at the same temperature for 6 hours. After the reaction was confirmed by HPLC, triethylamine (7.99 g, 78.9 mmol) was added and stirred overnight at the same temperature. After the acetyl rearrangement was confirmed by HPLC, 5% sodium bicarbonate solution (400 mL) was added to the reaction solution and the mixture was separated. 20% saline solution (200 mL) was added to the organic layer and the mixture was separated. The organic layer was concentrated to 80 mL under reduced pressure, and toluene (400 mL) was added and concentrated to 80 mL under reduced pressure. Toluene (400 mL) was added again and concentrated to 80 mL under reduced pressure. Dehydrated toluene (120 mL) was added to obtain a colorless toluene solution of 2-O-acetyl-3,4,6-tris-O-benzyl-D-mannose (the compound represented by formula A-2). Example 2 2-O-acetyl-3,4,6-tris-O-benzyl-1-O-(2,2,2-trichloroacetylimino)-D-mannose (compound represented by formula A-3) [Chemical 201] A toluene solution (78.9 mmol) of 2-O-acetyl-3,4,6-tris-O-benzyl-D-mannose (the compound represented by formula A-2) was added to a 1 L flask, along with 12 mL of trichloroacetonitrile (118 mmol) and 119 μL of DBU (0.789 mmol). The mixture was stirred at 0°C under nitrogen for 2 hours. After confirming the reaction was complete by HPLC, acetic acid (45 μL, 0.789 mmol) was added to the reaction solution at 0°C to obtain a toluene solution (78.9 mmol) of 2-O-acetyl-3,4,6-tris-O-benzyl-1-O-(2,2,2-trichloroacetylimino)-D-mannose as a brown solution. This solution was used directly in the next step. <Synthesis of the Compound Represented by Formula A-11> The compound represented by formula A-11 was synthesized according to the following synthetic procedure 2. [Synthetic Procedure 2] [Chemical Engineering 202] Example 3 4-Methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-acetylated-β-D-galactopyranosyl)-β-D-glucopyranoside (compound represented by formula B-3) [Chemical 203] Add 2,3,4,6-tetra-O-acetylated-1-O(2,2,2-trichloroacetylatedinino)-α-D-galactofuranose (represented by formula B-1) (2.275 kg, 4.618 mol) and molecular sieve 4A powder (below 10 μm, 375 g) to a solution of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimino-β-D-glucopyranoside (represented by formula B-2) (2.508 kg, 4.211 mol) in dichloromethane (17.5 L) and a solution of β-D-glucopyranose (represented by formula B-1) (2.275 kg, 4.618 mol) and molecular sieve 4A powder (below 10 μm, 375 g) to a solution of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimino-β-D-glucopyranoside) (2.508 kg, 4.211 mol) in dichloromethane (17.5 L). After stirring at 20 °C to 30 °C for 20 minutes, cool to -20 °C to -10 °C and add trimethylsilane trifluoromethanesulfonate (140 g, 0.630 mol) dropwise over 3 minutes. After stirring at -5℃ to -10℃ for 3 hours, triethylamine (106 g, 1.05 mol) was added, and the temperature was raised to 0℃ to 5℃. The mixture was filtered through molecular sieve 4A and washed with toluene (5 L). The resulting solution was concentrated to 12.5 L under reduced pressure, and toluene (12.5 L) was added. The solution was then washed four times with a mixture of methanol (6.5 L) and water (18.5 L). The obtained organic layer was concentrated to 9 L under reduced pressure, and after adding toluene (25 L), it was concentrated to 7.5 L under reduced pressure to obtain a toluene solution (7.5 L) of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-acetylated-β-D-galactopyranosyl)-β-D-glucopyranoside (the compound represented by formula B-3). Example 4 4-Methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-β-D-galactopyranosyl-β-D-glucopyranoside (compound represented by formula B-4) [Chemical 204] To a toluene solution (7.5 L) of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-acetylated-β-D-galactopyranosyl)-β-D-glucopyranoside (represented by formula B-3), tetrahydrofuran (10 L), methanol (5 L), and methyl trifluoroacetate (538 g, 4.20 mol) were added, followed by the addition of potassium tert-butoxide-tetrahydrofuran solution (1 M, 2.1 L, 2.1 mol), and the mixture was stirred at 40°C–45°C for 2 hours. After cooling to 20℃~25℃, acetic acid (151 g) and ethyl acetate (25 L) were added respectively. The mixture was washed three times with a solution of sodium bicarbonate (750 g)-sodium chloride (750 g)-water (20 L) and once with a solution of sodium chloride (2.5 kg)-water (10 L). The obtained organic layer was concentrated to 7.5 L under reduced pressure. N,N-dimethylacetamide (25 L) and cyclopentyl methyl ether (37.5 L) were added separately, and the mixture was concentrated to 27.5 L under reduced pressure. Then, cyclopentyl methyl ether (12.5 L) was added, and the mixture was concentrated to 27.5 L under reduced pressure to obtain a 27.5 L solution of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-β-D-galactopyranosyl-β-D-glucopyranoside (the compound represented by formula B-4) in N,N-dimethylacetamide. Example 5 4-Methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside (compound represented by formula B-5) [Chemical 205] A solution of n-butyllithium-hexane (15.2%, 8.88 kg, 21.0 mol) was added dropwise to a solution of tributanol (1.56 kg, 21.0 mol) in hexane (3.28 kg) over a period of 4 hours at -15°C to 0°C. A solution of tributanol in lithium-hexane was then obtained by adding methyl trifluoroacetate (26.9 g, 0.170 mol). Benzyl bromide (5.03 kg, 29.4 mol) and molecular sieve 4A powder (below 10 μm, 750 g) were added dropwise to an N,N-dimethylacetamide solution (27.5 L) of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-β-D-galactopyranosyl-β-D-glucopyranoside (the compound represented by formula B-4). The mixture was kept at 35°C–45°C for 3 hours, and a lithium butoxide-hexane solution (12.1 kg) was added dropwise. After cooling to 20°C–25°C, acetic acid (378 g, 6.29 mol) was added. The mixture was filtered through molecular sieve 4A and washed with N,N-dimethylacetamide (7.5 L). After adding heptane (12.5 L) and performing separation washing, third butyl methyl ether (25 L) was added to the obtained N,N-dimethylacetamide layer, and separation washing was performed three times with water (20 L). The obtained organic layer was concentrated to 7.5 L under reduced pressure to obtain a third butyl methyl ether solution (7.5 L) of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside (the compound represented by formula B-5). Example 6. 4-Methoxyphenyl 3,6-di-O-benzyl-2-(2-carboxybenzylamine)-2-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside cinchonidine salt (compound represented by formula B-6) [Chemical 206] To a 7.5 L solution of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside (represented by formula B-5) in tert-butyl methyl ether, 12.5 L of tetrahydrofuran, 5 L of methanol, and 1 L of water were added, respectively. After cooling to 0-10°C, a 4-equivalent aqueous solution of sodium hydroxide (2.6 L, 10.4 mol) was added dropwise over 5 minutes. After stirring at 0-10°C for 6 hours, triethylamine (1.70 kg, 16.8 mol) was added, and the mixture was stirred at 20-30°C for 16 hours. After cooling to 0℃~10℃, 6 M hydrochloric acid (3.0 L, 18.0 mol) was added dropwise over 20 minutes, and the temperature was raised to 20℃~25℃. Ethyl acetate (20 L) was added, and the mixture was washed separately with water (17.5 L), followed by further washing with a sodium chloride (2.5 kg)-water (10 L) solution. The obtained organic layer was concentrated to 7.5 L under reduced pressure, and then ethyl acetate (17.5 L) was added, followed by further concentration to 7.5 L under reduced pressure. Ethyl acetate (30 L) and cinconidine (1.36 kg, 4.62 mol) were added to the obtained solution, and the mixture was stirred at 20℃~25℃ for 18 hours. After cooling to 0℃~5℃ for 1 hour, heptane (20 L) was added dropwise over 1 hour. After stirring directly at this temperature for 1.5 hours, the resulting crystals were filtered. The crystals were then washed with a mixed solvent of ethyl acetate (7.5 L) and heptane (5.6 L) cooled to 0°C–5°C. The crystals were dried under reduced pressure at 40°C to obtain 4-methoxyphenyl 3,6-di-O-benzyl-2-(2-carboxybenzylamine)-2-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside cinchonidine salt (the compound represented by formula B-6) (5.10 kg, general yield of 4 steps 85.0%). 1 H-NMR (500 MHz, CDCl) 3) δ 8.78 (d, 4.6 Hz, 1H), 8.75 (d, J = 8.0 Hz, 1H), 8.07 (d, J = 8.5 Hz, 1H), 8.06 (d, J = 8.0 Hz, 2H), 7.65 - 7.68 (m, 3H), 7.61 (dd, 3.9,7.7 Hz, 1H), 7.55 (d, J = 4.6 Hz, 1H), 7.43 (dd, 3.7, 7.4 Hz, 2H), 7.19 - 7.33 (m, 28H), 6.98 - 7.04 (m, 5H), 6.68 - 6.70 (m, 2H), 6.32 (brd, 1H), 5.39 - 5.46 (m, 1H), 5.35 (d, J = 6.9 Hz, 1H), 4.97 (d, J = 11 Hz, 1H), 4.83 - 4.91 (m, 3H), 4.66 - 4.73 (m, 5H), 4.55 (d, J = 12 Hz, 1H), 4.46 (s, 1H), 4.43 (d, J = 4.0 Hz, 1H), 4.35 (dd, J = 5.7, 12 Hz, 2H), 4.26 (d, J = 12 Hz, 1H), 4.22 (dd, J = 4.2,8.4 Hz, 1H), 4.03 - 4.09 (m, 3H), 3.92 (d, J = 2.6 Hz, 1H), 3.74 (d, J = 3.7 Hz, 2H), 3.67 - 3.70 (m, 4H), 3.57 - 3.60 (m, 1H), 3.54 (t, J = 7.9 Hz, 1H), 3.36 - 3.44 (m, 3H), 3.31 (t, J = 9.2 Hz, 1H), 3.12 (dd, 10, 14 Hz, 1H), 3.02 (d, J = 13 Hz, 1H), 2.93 (m, 1H), 2.36 (s, 1H), 1.86 - 1.89 (m, 2H), 1.81 (dd, J = 9.0, 13 Hz, 1H), 1.53 (dd, J = 4.7, 9.5 Hz, 1H), 1.09 (dd, J = 5.7, 11 Hz, 1H). 13 C-NMR (125 MHz, CDCl 3) δ 176.2, 169.5, 155.3, 151.6, 150.1, 148.0, 146.4, 138.88, 138.7, 138.53, 138.48, 138.39, 138.35, 138.26, 137.8, 133.4, 130.15, 130.07, 129.11, 128.73, 128.70, 128.51, 128.4, 128.34, 128.22, 128.2, 128.16, 127.95, 127.92, 127.83, 127.75, 127.57, 127.55, 127.43, 127.41, 127.19, 127.12, 124.9, 122.8, 119.5, 118.7, 116.2, 114.3, 103.2, 100.3, 82.4, 79.8, 78.7, 76.2, 75.2, 75.1, 74.8, 73.7, 73.4, 73.03, 72.99, 72.7, 68.7, 68.1, 59.8, 55.5, 55.3, 54.1, 43.4, 37.6, 27.0, 25.0, 19.1 HRMS (ESI) + )[M+HNEt 3] + C 75 H 85 N 2O 14 Calculated value: 1237.5995; Experimental value: 1237.5977. [α] D 20 =-21.889(c 1.003, DCl 3). Example 7: 4-Methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-di-oxo-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside (the compound represented by formula B-5) [Chemical 207] A suspension of 3,500 kg (3.15 mol) of methoxyphenyl 3,6-di-O-benzyl-2-(2-carboxybenzylamine)-2-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside cinchonidine salt (the compound represented by formula B-6) in ethyl acetate (33.8 L) was added at 15°C–25°C, and the mixture was stirred and dissolved. After removing the aqueous layer, the mixture was separated and washed with a sodium chloride (4.5 kg)-water (18 L) solution. The obtained organic layer was concentrated to 6.8 L under reduced pressure. Ethyl acetate (33.8 L) was added, and the mixture was concentrated to 6.8 L under reduced pressure to obtain an ethyl acetate solution of the compound represented by formula B-7. [Chem. 208] Tetrahydrofuran (18 L) was then added to the obtained solution. After cooling to 0°C–5°C, 1,1'-carbonyldiimidazole (765 g, 4.12 mol) was added and the mixture was stirred for 17 hours. The aqueous layer was removed after adding ethyl acetate (22.5 L), water (22.5 L), and 6 M hydrochloric acid (1.57 L, 9.42 mol), respectively. The obtained organic layer was then washed sequentially with water (22.5 L) and sodium chloride (4.5 kg)-water (18 L) solution. The obtained organic layer was concentrated to 4.5 L under reduced pressure, and toluene (22.5 L) was added. The concentration was then carried out to 4.5 L under reduced pressure to obtain a toluene solution (4.5 L) of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside (the compound represented by formula B-5). Example 8 3,6-Di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranose (compound represented by formula B-8) [Chemical 209] To a toluene solution (4.5 L) of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside (represented by formula B-5), dichloromethane (6.75 L), 1,1,1,3,3,3-hexafluoro-2-propanol (6.75 L), and water (675 mL) were added at 15°C–25°C. A suspension of bis(trifluoroacetoxy)iodobenzene (2.16 kg, 5.02 mol) in dichloromethane (6.75 L) was divided into 10 fractions for addition, and the fractions were stirred at 15°C–25°C for 20 hours. The solution was cooled to 0℃~5℃, and toluene (31.5 L) was added. The mixture was then separated and washed twice with a sodium bicarbonate (900 g)-sodium sulfite (900 g)-water (22.5 L) solution at 0℃~20℃. The resulting organic layer was separated and washed with a sodium chloride (4.5 kg)-water (18 L) solution, then concentrated to 9 L under reduced pressure. Toluene (22.5 L) was added, and the solution was concentrated to 9 L under reduced pressure. Toluene (36 L) was added to the resulting solution, and the solution was divided into two fractions. Silicone (4.5 kg) was added to each fraction, and the mixture was stirred at 20℃~25℃ for 3 hours. The silicone was then filtered and washed with toluene (45 L). The silicone was then washed with a mixed solution of ethyl acetate (7.5 L)-toluene (22.5 L) to remove desorption from the silicone. The obtained organic layers were mixed and concentrated to 9 L under reduced pressure to obtain a toluene solution (9 L) of 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranose (the compound represented by formula B-8). 1 H-NMR (500 MHz, CDCl) 3) δ 7.60 - 7.87 (m, 4H), 7.18 - 7.36 (m, 25H), 6.96 (d, J = 6.9 Hz, 2H), 6.89 (m, 1H), 6.83 (dd, J = 7.4,10 Hz, 2H), 5.33 (dd, J = 1.9, 3.7 Hz, 0.2H), 5.30 (dd, J = 4.3, 8.6 Hz, 0.8H), 4.92 (dd, J = 9.9, 12 Hz, 2H), 4.78 - 4.86 (m, 2H), 4.71 (d, J = 2.3 Hz, 2H), 4.44 - 4.61 (m, 3H), 4.36 - 4.14 (m, 3H), 4.34 (d, J = 4.6 Hz, 1H), 4.26 (d, J = 12 Hz, 1H), 4.03 - 4.12 (m, 2H), 3.89 (d, J = 2.8 Hz, 1H), 3.85 (dd, J = 4.0, 11 Hz, 1H), 3.77 (dd, J = 7.7, 9.7 Hz, 1H), 3.67 (dd, J = 1.6, 11 Hz, 1H), 3.56 - 3.60 (m, 1H), 3.35 - 3.49 (m, 4H), 2.88 (d, J = 8.6 Hz, 1H). 13 C-NMR (125 MHz, CDCl 3) δ 168.2, 139.06, 139.04, 138.98, 138.91, 138.7, 138.6, 138.5, 138.10, 138.06, 133.8, 131.7, 128.40, 128.38, 128.32, 128.27, 128.24, 128.10, 127.99, 127.96, 127.90, 127.84, 127.78, 127.76, 127.72, 127.68, 127.65, 127.63, 127.55, 127.51, 127.49, 127.44, 127.42, 127.3, 126.8, 123.6, 123.3, 102.9, 102.8, 93.1, 92.8, 82.34, 82.32, 80.02, 79.99, 77.8, 77.7, 76.6, 75.43, 75.39, 75.31, 74.53, 74.49, 74.33, 73.98, 73.72, 73.63, 73.41, 73.24, 73.20, 73.07, 72.63, 72.59, 70.6, 68.3, 68.0, 67.8, 57.7, 55.8, HRMS(ESI + [M+Na] + C 62 H 61 NNaO 12 Calculated value: 1034.4092; Experimental value: 1034.4071. [α] D 20 =+33.243(c 1.002, CDCl 3). Example 9 3,6-Di-O-benzyl-2-deoxy-2-(1,3-di-oxo-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1-O-(2,2,2-trifluoro-N-phenylacetylino)-β-D-glucopyranose (the compound represented by formula A-11) [Chemical 210] Dichloromethane (2.0 L), molecular sieve 4A powder (below 10 μm, 250 g), and N-methylimidazolium (34.4 g, 0.419 mol) were added to a toluene solution (total: 1002 g) of 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranose (the compound represented by formula B-8) (500 g of the compound represented by free formula B-6, 0.349 mol of the solution obtained in Examples 7 and 8) at 20℃~30℃. Subsequently, 2,2,2-trifluoro-N-phenyliminoacetyl chloride (79.8 g, 0.384 mol) was added, and the mixture was stirred at 20°C–30°C for 17 hours. After filtration through molecular sieve 4A, the solution was washed with toluene (500 mL) and cooled to 0°C–10°C. The solution was then passed through a column filled with silicone (1.5 kg) moistened with dichloromethane cooled to 0°C–5°C, and washed with dichloromethane cooled to 0°C–5°C (15 L), with fractions of 2.5 L–3 L obtained each time. The solution was then washed with a mixture of dichloromethane (10 L) containing 3% ethyl acetate, with fractions of 2.5 L–3 L obtained each time. The first to seventh fractions obtained were combined and concentrated to 1 L under reduced pressure to obtain a toluene-dichloromethane mixture of 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1-O-(2,2,2-trifluoro-N-phenylacetylimino)-β-D-glucopyranose (the compound represented by formula A-11). This solution was used directly in Example 27. 1 H-NMR (500 MHz, CDCl) 3) δ 7.62 - 7.82 (m, 4H), 7.01 - 7.53 (m, 31H), 6.98 - 7.01 (m, 1H), 6.95 (d, J = 7.2 Hz, 2H), 6.80 - 6.88 (m, 3H), 6.64 (brd, 2H), 4.93 (d, J = 12 Hz, 1H), 4.89 (d, J = 12 Hz, 1H), 4.83 (d, J = 11 Hz, 1H), 4.77 (d, J = 11 Hz, 1H), 4.67 - 4.72 (m, 2H), 4.56 (d, J = 12 Hz, 1H), 4.53 (d, J = 12 Hz, 1H), 4.36 - 4.48 (m, 5H), 4.28 (d, J = 12 Hz, 1H), 4.14 (t, J = 8.7 Hz, 1H), 3.89 (d, J = 2.6 Hz, 1H), 3.85 (d, J = 7.7 Hz, 1H), 3.76 (t, J = 8.4 Hz, 1H), 3.38 - 3.50 (m, 4H). 13 C-NMR (125 MHz, CDCl 3) δ 167.6, 143.4, 143.1, 139.0, 138.68, 138.66, 138.5, 137.08, 137.06, 135.2, 133.92, 131.5, 129.3, 129.1, 129.0, 128.5, 128.41, 128.37, 128.31, 128.27, 128.22, 128.90, 127.86, 127.69, 127.56, 127.45, 127.44, 127.2, 126.9, 126.2, 124.3, 123.4, 120.6, 120.5, 119.3, 116.3 (q, J = 148.5 Hz), 102.9, 93.5, 82.3, 79.9, 76.6, 76.0, 75.4, 74.5, 73.61, 73.41, 73.08, 73.05, 72.6, 68.3, 67.2, 54.8. HRMS(ESI + )[M+Na] +C 70 H 65 F 3N 2NaO 12 Calculated value: 1205.4387; Experimental value: 1205.43835. [α] D 20 =+66.645(c 1.099, CDCl) 3). <Synthesis of the Compound Represented by Formula A-13> The compound represented by formula A-13 was synthesized according to the following synthetic procedure 3. [Synthetic Procedure 3] [Chemical Engineering 211] Example 10 1,2:5,6-bis-O-(1-methylethylidene)-3-O-(2-naphthylmethyl)-α-D-furanose (compound represented by formula C-2) [Chemical 212] A solution of sodium hydride (55.32 g, 1.38 mol, purity: 50-72%) in tetrahydrofuran (900 mL) was cooled to 0°C, and then a solution of 1,2:5,6-bis-O-(1-methylethylidene)-α-D-furanose (compound represented by formula C-1) (300.00 g, 1.15 mol) in tetrahydrofuran (1.05 L) was added dropwise over 1 hour. Subsequently, the temperature was raised to 25°C, and 1,3-dimethyl-2-imidazolidineone (150 mL) and 2-bromomethylnaphthalene (280.31 g, 1.27 mol) were added. After stirring at 25°C for 6 hours, the reaction was confirmed to be complete by HPLC, and anhydrous ethylenediamine (13.85 g, 230.52 mmol) was added, followed by stirring for 1 hour. The solution was then cooled to 0°C, and a 10% citric acid aqueous solution (1.2 L) was added over 1 hour. The reaction solution was diluted with heptane (3 L) to separate an organic layer and an aqueous layer. The organic layer was washed with water (900 mL) and concentrated under reduced pressure to a volume of 900 mL. Acetonitrile (3 L) was then added, and the solution was concentrated again to a volume of 900 mL to obtain an acetonitrile solution of the crude product 1,2:5,6-bis-O-(1-methylethylidene)-3-O-(2-naphthylmethyl)-α-D-furanose (the compound represented by formula C-2). This solution was used directly in the next step. Example 11 3-O-(2-naphthylmethyl)-D-glucopyranose (compound represented by formula C-3) [Chemical 213] Acetonitrile (1.5 L), water (600 mL), and concentrated hydrochloric acid (17.51 ​​g, 172.89 mmol) were added to a solution (900 mL) of the crude product represented by formula C-2 obtained in Example 10, and the mixture was stirred at 55°C for 18.5 hours. After the reaction was confirmed by HPLC, the reaction solution was cooled to 0°C, and the pH of the system was adjusted to 6.25 with 4 equivalence sodium hydroxide aqueous solution (43.22 mL). The reaction solution was diluted with heptane (900 mL) to separate the acetonitrile layer and the heptane layer. Ethyl acetate (2.4 L) and water (600 mL) were added to the acetonitrile layer, and the mixture was separated to obtain organic layer A and aqueous layer. A mixed solution of ethyl acetate (1.5 L) and tetrahydrofuran (1.5 L) was added to the aqueous layer again, and the mixture was separated to obtain organic layer B and aqueous layer. Organic layers A and B were mixed, washed with saturated brine (600 mL), and concentrated under reduced pressure to a volume of 1.5 L (crystallization was confirmed during the concentration stage). Ethyl acetate (4.5 L) was then added, and the mixture was concentrated again to a volume of 3 L. Ethyl acetate (1.5 L) and cyclopentyl methyl ether (1.5 L) were added to this suspension, and the mixture was stirred at 55°C for 1 hour. Heptane (3 L) was added dropwise over 1.5 hours, and the mixture was stirred for 1 hour, then cooled to 0°C. The precipitated crystals were then filtered and washed with a mixture of ethyl acetate (1.2 L) and heptane (600 mL) cooled to 0°C. The obtained crystals were dried under reduced pressure at 40°C to obtain 3-O-(2-naphthylmethyl)-D-pyranose (the compound represented by formula C-3) (356.95 g, yield 96.7%). 1 H-NMR (500 MHz, DMSO-d) 6) δ 7.85 - 7.90 (m, 4H), 7.59 (dd, J = 8.0, 1.5 Hz, 1H), 7.46 - 7.51 (m, 2H), 6.69 (d, J = 6.0 Hz, 1H), 5.12 (dd, J = 5.0, 3.0 Hz, 2H), 4.94 - 5.00 (m, 2H), 4.53 (t, J = 6.0 Hz, 1H), 4.35 (dd, J = 8.0, 6.5 Hz, 1H), 3.70 (ddd, J = 11.5, 5.0, 2.0 Hz, 1H), 3.45 - 3.50 (m, 1H), 3.25 - 3.31 (m, 2H), 3.11 - 3.16 (m, 2H). 13C-NMR (125 MHz, DMSO-d 6) δ 137.3, 132.8, 132.3, 127.6, 127.5, 127.4, 126.1, 126.0, 125.6, 125.5, 96.9, 85.4, 76.7, 74.8, 73.7, 69.9, 61.1. HRMS(ESI - [MH] - C 17 H 20 O 6: Calculated value: 320.1260; Experimental value: 319.1175. Example 12 2,4,6-Tri-O-acetylated-3-O-(2-naphthylmethyl)-D-glucopyranose (compound represented by formula C-5) [Chemical 214] Triethylamine (236.92 g, 2.34 mol) and 4-dimethylaminopyridine (0.29 g, 2.34 mmol) were added to a tetrahydrofuran (675 mL) solution of 3-O-(2-naphthylmethyl)-D-pyranose (compound represented by formula C-3) (150.00 g, 468.25 mmol). After cooling to 0°C, acetic anhydride (195.99 g, 1.92 mol) was added dropwise over 30 minutes. The mixture was then heated to 25°C and stirred for 3 hours. The reaction was confirmed to be complete by HPLC. The reaction solution was cooled to 10°C, and 1-methylpiperazine (60.97 g, 608.73 mmol) was added. After stirring at 35°C for 18 hours, the reaction was confirmed to be complete by HPLC and then cooled to 0°C. The pH was adjusted to 6.36 using 6 equivalence hydrochloric acid (480 mL), and then diluted with heptane (375 mL) to separate the organic and aqueous layers. The organic layer was washed with saturated sodium bicarbonate aqueous solution (450 mL) and water (450 mL), and then concentrated under reduced pressure to a volume of 450 mL. Ethyl acetate (2.25 L) was added, and the solution was concentrated again to a volume of 450 mL, and this process was repeated once more. Dichloromethane (2.25 L) was added to this solution, and the solution was concentrated to a volume of 450 mL, and this process was repeated once more to obtain a dichloromethane solution of the crude product 2,4,6-tri-O-acetylated-3-O-(2-naphthylmethyl)-D-glucopyranose (the compound represented by formula C-5). This solution was used directly in the next step. Furthermore, the step of converting the compound represented by formula C-3 to the compound represented by formula C-5 is carried out using a single-tank method. Example 13 2,4,6-Tri-O-acetylated-3-O-[(naphth-2-yl)methyl]-1-O-(2,2,2-trichloroacetylinimino)-D-glycerol-hexose pyranose (compound represented by formula C-6) [Chemical 215] To a solution (450 mL) of the crude product obtained in Example 12, consisting of 2,4,6-tri-O-acetylated-3-O-(2-naphthylmethyl)-D-glucopyranose (the compound represented by formula C-5), dichloromethane (450 mL) and trichloroacetonitrile (338.03 g, 2.34 mol) were added and the mixture was cooled to 0°C. Then, 1,8-diazabicyclo[5.4.0]-7-undecene (5.70 g, 37.46 mmol) was added dropwise. After stirring at 0°C for 14.5 hours, the reaction was confirmed to be complete by HPLC, and acetic acid (2.25 g, 37.46 mmol) was added. Silicone 60N (manufactured by Kanto Chemical, particle size: 40–50 μm, 150 g) was added to the solution, and the mixture was stirred for 1.5 hours before filtration. The silicone was washed with dichloromethane (1.5 L), and the filtrate was concentrated under reduced pressure to a volume of 450 mL. Then, dichloromethane (1.5 L) was added, and the solution was concentrated to a volume of 450 mL to obtain a dichloromethane solution of 2,4,6-tri-O-acetylated-3-O-[(naphthyl-2-yl)methyl]-1-O-(2,2,2-trichloroacetylino)-D-glycerol-hexose pyranose (the compound represented by formula C-6). This solution was used directly in the next step. Example 14 4-Methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-{2,4,6-tri-O-acetylglyl-3-O-[(naphthyl-2-yl)methyl]-β-D-glucopyranoside}-β-D-glucopyranoside (compound represented by formula C-8) [Chemical 216] To a solution (450 mL) of 2,4,6-tri-O-acetylated-3-O-[(naphth-2-yl)methyl]-1-O-(2,2,2-trichloroacetylimino)-D-glycerol-hexose pyranose (the compound represented by formula C-6), 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula C-7) (276.66 g, 468.25 mmol), dichloromethane (4.2 L), and molecular sieve 4A powder (below 10 μm, 83.00 g) obtained in Example 13, the mixture was added and cooled to -5°C. Trimethylsilane trifluoromethanesulfonate (10.41 g, 46.83 mmol) was added dropwise to the suspension over a period of 20 minutes, followed by stirring for 3 hours. After confirming the completion of the reaction by HPLC, triethylamine (23.69 g, 234.13 mmol) was added. The suspension was filtered, washed with ethyl acetate (2.8 L), and the filtrate was concentrated under reduced pressure to a volume of 1.4 L. Ethyl acetate (4.2 L) was then added, and the volume was concentrated to 1.4 L, and this process was repeated once more. Ethyl acetate (2.8 L) was added to this solution, and the solution was washed with saturated sodium bicarbonate aqueous solution (830 mL) and water (830 mL). The organic layer was concentrated under reduced pressure to a volume of 830 mL. 2-Propanol (4.2 L) was then added, and the solution was concentrated to a volume of 1.4 L. The suspension was then heated to 65°C. Ethyl acetate (830 mL) was added and stirred at 65 °C for 2 hours, followed by dropwise addition of 2-propanol (5.53 L) over 2 hours. The suspension was cooled to 0 °C, and the crystals were filtered and washed with 2-propanol (1.4 L) cooled to 0 °C. The obtained crystals were dried under reduced pressure at 40 °C to obtain the crude product 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-{2,4,6-tri-O-acetylglyl-3-O-[(naphthyl-2-yl)methyl]-β-D-glucopyranoside}-β-D-glucopyranoside (the compound represented by formula C-8) (355.34 g, yield 90.5%, based on the compound represented by formula C-3). Methyl isobutyl ketone (2.1 L) was added to the crude product represented by formula C-8 (350.00 g), dissolved at 50 °C, and then ethylcyclohexane (1.4 L) was added dropwise over 1 hour.Add 70.00 mg of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-di-dihydro-2H-isoindol-2-yl)-4-O-{2,4,6-tri-O-acetylgly-3-O-[(naphthyl-2-yl)methyl]-β-D-glucopyranoside}-β-D-glucopyranoside (the compound represented by formula C-8) and stir for 1 hour. After confirming the precipitation of crystals, add 4.9 L of ethylcyclohexane dropwise over 2 hours. Cool the suspension to room temperature and stir for 14.5 hours. Filter the precipitated crystals and wash them with a mixed solution of methyl isobutyl ketone (350 mL) and ethylcyclohexane (1.4 L). The obtained crystals were dried under reduced pressure at 40°C to obtain 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-di-dihydro-2H-isoindol-2-yl)-4-O-{2,4,6-tri-O-acetylglyl-3-O-[(naphthyl-2-yl)methyl]-β-D-glucopyranoside}-β-D-glucopyranoside (the compound represented by formula C-8) (331.74 g, yield 94.8%). 1 H-NMR (500 MHz, CDCl) 3) δ 7.81 - 7.84 (m, 4H), 7.69 (br, 1H), 7.65 (br, 3H), 7.46 - 7.51 (m, 2H), 7.28 - 7.36 (m, 6H), 7.00 (dd, J = 7.0, 1.5 Hz, 2H), 6.77 - 6.84 (m, 5H), 6.66 - 6.69 (m, 2H), 5.59, (d, J = 9.0 Hz, 1H), 5.09 - 5.15 (m, 2H), 4.82 (d, J = 12.5 Hz, 1H), 4.77 (d, J = 12.0 Hz, 1H), 4.71 - 4.77 (m, 2H), 4.60 (d, J = 8.0 Hz, 1H), 4.50 (d, J = 12.5 Hz, 1H), 4.45 (d, J = 13.0 Hz, 1H), 4.36 (dd, J = 11.0, 8.5 Hz, 1H), 4.28 (dd, J = 11.0, 8.5 Hz, 1H), 4.20 (dd, J = 12.5, 5.0 Hz, 1H), 4.10 (dd, J = 10.0, 8.5 Hz, 1H), 3.99 (dd, J = 12.0, 2.0 Hz, 1H), 3.80 (br, 2H), 3.69 (s, 3H), 3.58 - 3.62 (m, 2H), 3.44 (ddd, J = 10.0, 4.5, 2.5 Hz, 1H), 1.98 (s, 3H), 1.938 (s, 3H), 1.937 (s, 3H). 13 C-NMR(125 MHz, CDCl 3) δ 171.0, 169.5, 169.1, 155.6, 151.0, 138.7, 138.2, 135.5, 133.9, 133.4, 133.2, 128.7, 128.4, 128.23, 128.20, 128.06, 128.05, 127.9, 127.2, 126.5, 126.2, 125.7, 123.5, 118.9, 114.5, 100.7, 97.8, 80.6, 78.5, 76.8, 75.2, 74.8, 74.1, 73.8, 73.1, 72.1, 69.9, 67.8, 62.2, 55.78, 55.75, 21.1, 20.94, 20.85. HRMS(ESI + [M+H] + C 58 H 58 NO 16 Calculated value: 1024.3750; Experimental value: 1024.3706. The spectrum was confirmed to be consistent with the following literature: Org. Bio mol. Chem., 2018, 16, 4720-4727. Example 15 4-Methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-{3-O-[(naphthyl-2-yl)methyl]-β-D-glucopyranoside}-β-D-glucopyranoside (compound represented by formula C-9) [Chemical 217] A solution of 30.00 g (29.29 mmol) of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-{2,4,6-tri-O-acetylated-3-O-[(naphthyl-2-yl)methyl]-β-D-glucopyranoside}-β-D-glucopyranoside (the compound represented by formula C-8) in tetrahydrofuran (150 mL) was added with methanol (90 mL) and methyl trifluoroacetate (3.75 g, 29.29 mmol). The mixture was stirred at 25 °C for 10 min, followed by the addition of potassium terbutoxide (1 mol / L tetrahydrofuran solution) (14.7 mL, 14.65 mmol). The mixture was then heated to 55 °C and stirred for 2 hours. The reaction was then confirmed to be complete by HPLC. The reaction solution was cooled to 25°C, and acetic acid (1.76 g, 29.29 mmol) and ethyl acetate (300 mL) were added sequentially. The solution was washed twice with 1% sodium chloride aqueous solution (300 mL), and then concentrated under reduced pressure to a volume of 90 mL. Ethyl acetate (450 mL) was added, and the solution was concentrated again to a volume of 90 mL. Acetonitrile (450 mL) was then added, and the solution was concentrated to a volume of 90 mL, yielding an acetonitrile solution of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-{3-O-[(naphthyl-2-yl)methyl]-β-D-glucopyranoside}-β-D-glucopyranoside (the compound represented by formula C-9). This solution was used directly in the next step. Example 16 4-Methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylidene-3-O-[(naphth-2-yl)methyl]-β-D-glucopyranoside}-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (compound represented by formula C-10) [Chemical 218] To a solution (90 mL) of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-{3-O-[(naphthyl-2-yl)methyl]-β-D-glucopyranoside}-β-D-glucopyranoside (the compound represented by formula C-9), acetonitrile (210 mL), benzaldehyde dimethyl acetal (5.13 g, 33.69 mmol), and p-toluenesulfonic acid monohydrate (0.17 g, 0.88 mmol) were added, and the mixture was stirred at 25 °C for 30 minutes. Toluene (600 mL) was then added to the solution, and the mixture was concentrated to a volume of 300 mL. The reaction was confirmed to be complete by HPLC at this point. Then, 1-methylimidazole (12.03 g, 146.47 mmol) was added, and the solution was concentrated to a volume of 90 mL to obtain a toluene solution containing 1-methylimidazole of 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylidene-3-O-[(naphth-2-yl)methyl]-β-D-glucopyranoside}-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula C-10). This solution was then used directly in the next step. Example 17 4-Methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylidene-3-O-[(naphth-2-yl)methyl]-2-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside}-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula C-11 (where X...) 1 is a Tf-based group) [Chem. 219] Ethyl acetate (210 mL) was added to a solution (90 mL, containing 1-methylimidazole) of 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylidene-3-O-[(naphthyl-2-yl)methyl]-β-D-glucopyranoside}-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula C-10), obtained in Example 16, and the solution was cooled to 0°C. Trifluoromethanesulfonic anhydride (16.53 g, 58.59 mmol) was added dropwise to the solution over 1 hour, followed by stirring for 30 minutes. After confirming the completion of the reaction by HPLC, water (300 mL) was added, and the solution was separated into an organic layer and an aqueous layer. The organic layer was washed twice with water (300 mL) and once with a saturated sodium chloride aqueous solution (150 mL). The solution was then concentrated under reduced pressure to a volume of 90 mL. Ethyl acetate (300 mL) was added, and the solution was concentrated again to a volume of 90 mL to obtain 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylene-3-O-[(naphthyl-2-yl)methyl]-2-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside}-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (represented by formula C-11). 1 is an ethyl acetate solution of Tf group. This is used directly in the next step. Example 18 4-Methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylene-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose}-2-(2-carboxybenzylamine)-2-deoxy-β-D-glucopyranoside (compound represented by formula C-13) [Chemical 220] The compound represented by formula C-11 (where X is a 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylene-3-O-[(naphth-2-yl)methyl]-2-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside obtained in Example 17) is a 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzyl-3-O-[(naphth-2-yl)methyl]-2-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside (where X is a 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylene-3-O-[(naphth-2-yl)methyl]-2-O-(trifluoromethanesulfonyl)-β-D-glucopyranoside) obtained in Example 17. Dimethyl sulfoxide (150 mL) and tetrabutylammonium acetate (17.67 g, 58.59 mmol) were added to a 90 mL solution of Tf-based methyl sulfoxide, and the mixture was heated to 30 °C and stirred for 17 hours. The reaction was then confirmed to be complete by HPLC. Toluene (150 mL) was added to the reaction mixture, and the solution was concentrated to 165 mL under reduced pressure. Methanol (45 mL) and 50% sodium hydroxide aqueous solution (3.52 g, 87.88 mmol) were added, and the mixture was stirred at 25 °C for 1.5 hours. After the reaction was confirmed to be complete by HPLC, ethyl acetate (450 mL) and water (300 mL) were added for separation. Water (300 mL) was added to the organic layer, and the mixture was cooled to 0 °C. The pH was adjusted to 2.73 using 6 equivalence hydrochloric acid with thorough stirring. Tetrahydrofuran (300 mL) was added to the separated organic layer, and the mixture was concentrated to 150 mL under reduced pressure. Add tetrahydrofuran (300 mL), concentrate again to a volume of 90 mL, and adjust the internal temperature to 45°C. Add tetrahydrofuran (60 mL), cool to 25°C, add 2-propanol (150 mL) and water (15 mL), and add 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylidene-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose}-2-(2-carboxybenzophenamine)-2-deoxy-β-D-glucopyranoside (the compound represented by formula C-13) (30 mg). Stir at 25°C for 14 hours. After confirming the precipitation of crystals, add 2-propanol (210 mL) dropwise over 1 hour, and cool to 0°C. After stirring for 2 hours, filter the precipitated crystals and wash them with 2-propanol (150 mL) cooled to 0°C. The obtained crystals were dried under reduced pressure at 40°C to obtain 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylene-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose}-2-(2-carboxybenzophenamine)-2-deoxy-β-D-glucopyranoside (the compound represented by formula C-13) (27.74 g, yield 94.3%, based on the compound represented by formula C-8). ※The step from the compound represented by formula C-12 to the compound represented by formula C-13 was performed using a single-tank method. ※Regarding seed crystals, a portion of the reaction solution was separated, concentrated, and the solid precipitated. *Regarding this reaction, the reaction proceeds well when using tetrabutylammonium acetate manufactured by Tokyo Chemical Industry Co., Ltd. (product code: T2694, purity: >90.0%) and Sigma-Aldrich Corporation (product code: 86849, purity: >90%). Furthermore, other manufacturers sometimes include excess acetic acid in their tetrabutylammonium acetate, in which case the reaction tends to be significantly delayed.As an alternative method, the same conversion reaction can be carried out using cesium acetate (details are described below). ※ The conversion of the compound represented by formula C-11 to the compound represented by formula C-12 can also be carried out under the conditions of cesium acetate (3 equivalents), dimethyl sulfoxide, 50°C, and 24 hours. Subsequently, by carrying out the same reaction (compound represented by formula C-12 to the compound represented by formula C-13) and post-treatment, the compound represented by formula C-13 was obtained. 1 H-NMR (500 MHz, CDCl) 3) δ 8.02 (dd, J = 6.0, 2.0 Hz, 1H), 7.69 - 7.83 (m, 4H), 7.38 - 7.49 (m, 12H), 7.32 - 7.34 (m, 2H), 7.16 - 7.29 (m, 8H), 6.97 (ddd, J = 9.0, 4.0, 2.5 Hz, 2H), 6.76 (ddd, J = 9.5, 3.5, 2.5 Hz, 2H), 5.51 (s, 1H), 5.40 (d, J = 6.0 Hz, 1H), 4.83 - 4.91 (m, 3H), 4.76 (d, J = 11.5 Hz, 1H), 4.55 (d, J = 0.5 Hz, 1H), 4.49 (d, J = 12.0 Hz, 1H), 4.36 (d, J = 12.0 Hz, 1H), 4.26 - 4.30 (m, 1H), 4.16 (t, J = 6.5 Hz, 1H), 4.05 - 4.09 (m, 2H), 3.99 (dd, J = 3.0, 0.5 Hz, 1H), 3.93 (t, J = 9.5 Hz, 1H), 3.80 - 3.86 (m, 2H), 3.71 (s, 3H), 3.65 - 3.69 (m, 1H), 3.56(t, J = 10.0 Hz, 1H), 3.51 (dd, J = 10.0, 3.5 Hz, 1H), 3.13(td, J = 9.5, 5.0 Hz, 1H). 13 C-NMR (125 MHz, CDCl) 3) δ 170.9, 168.4, 155.3, 151.4, 138.7, 138.0, 137.6, 136.2, 135.4, 133.4, 133.3., 132.2, 132.1, 130.7, 130.3, 129.2, 128.6, 128.49, 128.45, 128.11, 128.07, 128.0, 127.89, 127.87, 127.8, 126.8, 126.4, 126.3, 126.2, 125.8, 118.6, 114.7, 101.7, 100.4, 99.1, 78.3, 76.7, 76.4, 75.1, 73.7, 73.3, 72.5, 69.9, 69.4, 68.5, 67.0, 55.8, 54.4. HRMS(ESI + [M+H] + C 59 H 58 NO 14 Calculated value: 1004.3852; Experimental value: 1004.3873. Example 19 4-Methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylidene-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose}-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (compound represented by formula C-14) [Chemical 221] To a solution of 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylidene-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose}-2-(2-carboxybenzopyridine)-2-deoxy-β-D-glucopyranoside (the compound represented by formula C-13) (6.00 g, 5.98 mmol) in dichloromethane (30 mL), 1-hydroxybenzotriazole monohydrate (0.18 g, 1.20 mmol), N,N-diisopropylethylamine (0.85 g, 6.57 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.26 g, 6.57 mmol) were added and the mixture was heated to 40 °C and stirred for 31 hours. After confirming the completion of the reaction by HPLC, the reaction solution was cooled to 0°C, and ethyl acetate (90 mL) and water (60 mL) were added. Hydrochloric acid with a concentration of 6 equivalents was added to bring the pH to 7 with thorough stirring. The organic layer was separated from the aqueous layer, and the organic layer was washed with water (60 mL) and saturated saline solution (30 mL). The solution was concentrated under reduced pressure to a volume of 12 mL. Tetrahydrofuran (60 mL) was added, and the solution was concentrated again to a volume of 9 mL to obtain a tetrahydrofuran solution of the crude product 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylidene-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose}-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula C-14). Use it directly in the next step. Example 20 4-Methoxyphenyl 3,6-di-O-benzyl-4-O-{2-O-benzyl-4,6-O-benzylidene-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose}-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (compound represented by formula C-15) [Chem. 222] To a solution of the crude product 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{4,6-O-benzylene-3-O-[(naphthyl-2-yl)methyl]-β-D-mannopyranose}-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula C-14), N,N-dimethylacetamide (60 mL), benzyl bromide (1.53 g, 8.96 mmol), methyl trifluoroacetate (0.15 g, 1.20 mmol), and molecular sieve 4A (1.8 g) were added and the mixture was cooled to 0 °C. A solution of lithium tributoxide in tetrahydrofuran was then added (Note: This solution uses 2-methyl-2-propanol (0.66 g, 8.96 mmol) and tetrahydrofuran (2.4 g). A mixed solution of n-butyllithium (1.55 mol / L) was cooled to 0°C, and a hexane solution of 1.55 mol / L (5.78 mL, 8.96 mmol) was added and stirred for 30 minutes, followed by stirring for 3 hours. After the reaction was confirmed by HPLC, anhydrous ethylenediamine (0.18 g, 2.99 mmol) was added, and the mixture was stirred for 1 hour. Acetic acid (0.72 g, 11.95 mmol) was added to the solution and the mixture was filtered. Molecular sieve 4A was washed with ethyl acetate (90 mL), and water (60 mL) was added for separation. The organic layer was washed twice with water (60 mL) and concentrated under reduced pressure to a volume of 12 mL. Toluene (30 mL) was added, and the mixture was concentrated again to a volume of 12 mL. Toluene (18 mL) and silicone 60N (spherical, manufactured by Kanto Chemical, particle size: 40–50 μm) (9 g) were added, and the mixture was stirred at 25°C for 30 minutes. The suspension was filtered, and the silicone was washed with a mixed solution of toluene (191 mL) and ethyl acetate (19 mL). The filtrate was concentrated under reduced pressure to a volume of 9 mL to obtain a toluene solution of the crude product 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{2-O-benzyl-4,6-O-benzylidene-3-O-[(naphthyl-2-yl)methyl]-β-D-mannopyranose}-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula C-15). Example 21 4-Methoxyphenyl 3,6-di-O-benzyl-2-deoxy-4-O-{2,4-di-O-benzyl-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose}-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (compound represented by formula A-4) [Chemical 223] To a solution of the crude product obtained, 4-methoxyphenyl 3,6-di-O-benzyl-4-O-{2-O-benzyl-4,6-O-benzylidene-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose}-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula C-15), 5.50 g (5.48 mmol) was added. The solution was cooled to 0°C, and then borane-tetrahydrofuran complex (0.91 mol / L tetrahydrofuran solution) (18.06 mL, 16.43 mmol) and copper(II) trifluoroacetate (0.59 g, 1.64 mmol) were added. The solution was stirred for 3 hours. After confirming the completion of the reaction by HPLC, methanol (5.5 mL) was added, and the mixture was stirred for another 30 minutes. The solution was filtered, and molecular sieve 4A was washed with ethyl acetate (110 mL). Hydrochloric acid (55 mL) with a concentration of 0.5 equivalence was added, and the mixture was stirred for 30 minutes. After separating the organic layer from the aqueous layer, the organic layer was washed with hydrochloric acid (55 mL) with a concentration of 0.5 equivalence and saturated saline (27.5 mL). The solution was then concentrated and dried under reduced pressure. The compound was purified by silicone column chromatography (300 g silicone, hexane: ethyl acetate = 55:45 → 30:70) to obtain 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-4-O-{2,4-di-O-benzyl-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose}-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (represented by formula A-4) (4.94 g, yield 83.6%, HPLC area: 98.54%). 1 H-NMR (500 MHz, CDCl 3) δ 7.67 - 7.84 (m, 8H), 7.44 - 7.49 (m, 4H), 7.40 (dd, J = 8.0, 1.5 Hz, 1H), 7.21 - 7.33 (m, 13H), 6.87 - 6.93 (m, 5H), 6.82 (ddd, J = 9.5, 4.0, 2.5 Hz, 2H), 6.70 (ddd, J = 9.0, 4.0, 2.0 Hz, 2H), 5.64 (d, J = 8.5 Hz, 1H), 4.94 (d, J = 12.5 Hz, 1H), 4.91 (d, J = 10.0 Hz, 1H), 4.90 (s, 2H), 4.66 (s, 2H), 4.60 (d, J = 11.0 Hz, 1H), 4.59 (d, J = 12.0 Hz, 1H), 4.55 (s, 1H), 4.40 - 4.46 (m, 3H), 4.33 (dd, J = 11.0, 9.0 Hz, 1H), 4.06 (dd, J = 9.5, 8.5 Hz, 1H), 3.80 - 3.85 (m, 2H), 3.70 - 3.76 (m, 2H), 3.71 (s, 3H), 3.61 - 3.68 (m, 2H), 3.45 - 3.48 (m, 1H), 3.44 (dd, J = 9.5, 3.0 Hz, 1H), 3.23 (ddd, J = 9.5, 5.5, 2.5 Hz, 1H), 1.97 (br-t, 1H). 13 C-NMR(125 MHz, CDCl 3) δ 155.6, 151.1, 138.9, 138.64, 138.56, 138.0, 135.9, 134.0, 133.5, 133.2, 131.8, 128.7, 128.6, 128.4, 128.3, 128.20, 128.19, 128.15, 128.1, 120.04, 128.01, 127.9, 127.7, 127.6, 127.3, 126.4, 126.3, 126.1, 125.8, 123.6, 119.0, 114.6, 101.2, 98.0, 82.6, 79.0, 77.2, 75.9, 75.4, 75.3, 75.2, 75.1, 74.8, 74.7, 73.8, 72.1, 68.7, 62.6, 55.82, 55.78, 34.4, 30.5. HRMS(ESI - )[M+HCO 2] - C 67 H 64 NO 15 Calculated value: 1122.4281; Experimental value: 1122.4285. Implementation Example 22 [Chemistry 224] A toluene solution (equivalent to 78.4 mmol) of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-4-O-{2,4-di-O-benzyl-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose}-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (represented by formula A-4) (65.0 g, 60.3 mmol) and 2-O-acetylated-3,4,6-tri-O-benzyl-1-O-(2,2,2-trichloroacetylimino)-D-mannosyranose (represented by formula A-3) was added to a 1 L 4-diameter flask and dissolved in 650 mL of toluene. Molecular sieve 4A powder (below 10 μm, 13.0 g) was then added. Trimethylsilane trifluoromethanesulfonate (2.7 mL, 15.1 mmol) was added dropwise over 15 minutes at -15°C under nitrogen atmosphere, and the mixture was stirred for 30 minutes at the same temperature. After confirming the completion of the reaction by HPLC, triethylamine (4.2 mL, 30.2 mmol) was added, and the mixture was heated to room temperature. The reaction solution was filtered through diatomaceous earth and washed with acetonitrile (195 mL). The filtrate was concentrated under reduced pressure, and acetonitrile (650 mL) was added to the concentrated residue, followed by the addition of reverse-phase silica gel 120RP-18 (manufactured by Kanto Chemical, particle size: 40–50 μm, 97.5 g). Water (130 mL) was added dropwise over 30 minutes to adsorb the target compound onto the solid phase, followed by filtration. The solid phase was washed with acetonitrile / water (3 / 1, 326 mL) (the filtrate was discarded), and the target compound was desorbed using an acetonitrile (585 mL)-ethyl acetate (65 mL) solution. The filtrate was concentrated under reduced pressure to obtain 4-methoxyphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-3-O-[(naphthyl-2-yl)methyl]-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (represented by formula A-5) (70.5 g, single-isomeric yield 94%). 1 H-NMR (CDCl) 3) σ 7.85 - 7.80 (m, 1H), 7.78 (d, J = 8.6 Hz, 1H), 7.74 - 7.58 (m, 5H), 7.50 - 7.43 (m, 5H), 7.39 (dd, J = 8.6, 1.7 Hz, 1H), 7.32 - 7.02 (m, 30H), 6.92 - 6.89 (m, 2H), 6.78 - 6.76 (m, 2H), 6.71 - 6.62 (m, 5H), 5.59 (d, J = 8.6 Hz, 1H), 5.36 (dd, J = 2.9, 2.3 Hz, 1H), 5.00 - 4.90 (m, 4H), 4.87 (d, J = 12.6 Hz, 1H), 4.79 (d, J = 11.5 Hz, 1H), 4.66 - 4.50 (m, 7H), 4.43 (dd, J = 11.5, 2.3 Hz, 1H), 4.40 - 4.34 (m, 3H), 4.28 (dd, J = 10.3, 8.6 Hz, 1H), 4.22 (d, J = 11.5 Hz, 1H), 4.08 (dd, J = 9.7, 9.2 Hz, 1H), 3.94 (dd, J = 9.2, 9.2 Hz, 1H), 3.89 - 3.83 (m, 3H), 3.83 - 3.58 (m, 10H), 3.55 - 3.50 (m, 1H), 3.42 (dd, J = 9.2, 2.9 Hz, 1H), 3.37 - 3.31 (m, 1H), 1.90 (s, 3H). 13 C-NMR(CDCl 3) σ 167.0, 155.3, 150.8, 138.8, 138.7, 138.51, 138.49, 138.4, 138.0, 137.9, 135.6, 133.6, 133.2, 132.9, 131.6, 128.44, 128.41, 128.32, 128.26, 128.22, 128.19, 128.12, 127.86, 127.81, 127.75, 127.71, 127.69, 127.63, 127.56, 127.44, 127.37, 127.27, 127.0, 126.3, 126.2, 125.9, 125.7, 123.2, 118.7, 114.3, 101.9, 98.3, 97.6, 82.7, 79.6, 77.8, 76.6, 75.04, 74.98, 74.91, 74.89, 74.75, 74.4, 74.3, 74.1, 74.0, 73.4, 73.3, 71.70, 71.65, 71.3, 68.8, 68.6, 68.3, 67.1, 55.6, 55.5, 20.9. HRMS(ESI + )[M+HNEt 3] + C 101 H 109 N 2O 19 + Calculated value: 1654.7653; Experimental value: 1654.7618. [α] D 20 =+31.589(c 1.002, CDCl 3). Implementation Example 23 [Chemical Engineering 225] 4-Methoxyphenyl 2-O-acetylglucan-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula A-5) (44.0 g, 28.3 mmol) was added to a 1 L 4-bore flask, followed by dichloromethane (228 mL), 1,1,1,3,3,3-hexafluoro-2-propanol (163 mL), and water (14 mL). Under nitrogen atmosphere at 2°C, a solution of [bis(trifluoroacetoxy)iodide]benzene (25.9 g, 56.6 mmol) in dichloromethane (80 mL) and trifluoroacetic acid (6.9 mL, 84.9 mmol) was added, and the mixture was stirred for 8 hours at the same temperature. After confirming the completion of the reaction by HPLC, a solution of sodium bicarbonate (18.7 g) in water (228 mL) was added and stirred for 5 minutes, followed by the addition of a solution of sodium sulfite (11.7 g) in water (228 mL). After stirring for 5 minutes, the mixture was allowed to stand, and the dichloromethane layer was separated. The obtained organic layer was concentrated to 97.5 mL under reduced pressure, and then ethyl acetate (325 mL) and sodium chloride (23.4 g) in water (211 mL) solutions were added, respectively. After stirring for 5 minutes, the mixture was allowed to stand, and the organic layer was separated. The obtained organic layer was concentrated to 97.5 mL under reduced pressure, and then toluene (890 mL) was added, followed by further concentration to 97.5 mL under reduced pressure. Toluene (164 mL) and dichloromethane (65 mL) were added, followed by the addition of silicone 60N (manufactured by Kanto Chemical, particle size: 40–50 μm, 130 g), allowing the target analyte to adsorb onto the silicone before filtration. The sample was then washed with a dichloromethane (130 mL)-toluene (520 mL) solution (filtrate was discarded), and the target analyte was desorbed from the solid phase using an ethyl acetate (220 mL)-dichloromethane (455 mL) solution. The filtrate was concentrated under reduced pressure, and toluene (228 mL) was added. The solution was then concentrated to 97.5 mL under reduced pressure to obtain a toluene solution of 2-O-acetylglucan-3,4,6-tris-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-3-O-[(naphthyl-2-yl)methyl]-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-D-glucose pyranose (the compound represented by formula A-6). This solution was used directly in the next step. 1 H-NMR (CDCl) 3) σ 7.85 - 7.80 (m, 1H), 7.78 (d, J = 8.6 Hz, 1H), 7.72 (s, 1H), 7.70 - 7.64 (m, 1H), 7.63 (brs, 2H), 7.48 - 7.43 (m, 4H), 7.39 (dd, J = 8.6, 1.7 Hz, 1H), 7.33 - 7.10 (m, 30H), 6.92 - 6.87 (m, 2H), 6.77 - 6.66 (m, 3H), 5.38 (dd, J = 3.4, 1.7 Hz, 1H), 5.23 (dd, J = 8.6, 8.6 Hz, 1H), 4.97 - 4.86 (m, 4H), 4.84 (d, J = 12.6 Hz, 1H), 4.79 (d, J = 10.9 Hz, 1H), 4.63 (d, J = 11.5 Hz, 1H), 4.60 - 4.48 (m, 7H), 4.46 (d, J = 11.5 Hz, 1H), 4.37 (dd, J = 12.0, 3.4 Hz, 1H), 4.32 (dd, J = 10.9, 8.6 Hz, 1H), 4.23 (d, J = 10.9 Hz, 1H), 4.06 (dd, J = 9.2, 9.2 Hz, 1H), 4.01 (dd, J = 10.9, 9.2 Hz, 1H), 3.92 (dd, J = 9.2, 3.4 Hz, 1H), 3.89 - 3.74 (m, 6H), 3.72 - 3.65 (m, 2H), 3.64 - 3.57 (m, 2H), 3.48 (dd, J = 10.9, 1.1 Hz, 1H), 3.42 - 3.34 (m, 2H), 2.68 (dd, J = 9.2, 1.1 Hz, 1H), 1.95 (s, 3H). 13 C-NMR(CDCl 3) σ 170.2, 167.9, 138.85, 138.79, 138.6, 138.5, 138.4, 138.0, 137.8, 135.6, 133.6, 133.2, 132.9, 131.6, 128.55, 128.50, 128.33, 128.24, 128.20, 128.16, 127.9, 127.80, 127.75, 127.69, 127.66, 127.62, 127.54, 127.45, 127.36, 127.33, 126.97, 126.22, 126.17, 125.9, 125.6, 123.2, 101.1, 97.9, 92.9, 82.6, 78.6, 78.0, 76.1, 74.9, 74.8, 74.4, 74.15, 74.13, 74.0, 73.5, 73.2, 71.7, 71.6, 71.3, 68.8, 68.7, 68.4, 67.0, 57.6, 20.9. HRMS(ESI + )[M+HNEt 3] + C 94 H 103 N 2O 18 + Calculated value: 1548.7234; Experimental value: 1548.7237. [α] D 20 =+32.528(c 1.006, CDCl 3). Implementation Example 24 [Chemical Engineering 226] A toluene solution of 2-O-acetylglucan-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-D-glucose pyranose (represented by formula A-6) obtained in Example 23 was added to a 1L 4-bore flask, along with dichloromethane (260 mL) and molecular sieve 4A powder (below 10 μm, 21.8 g), and the mixture was cooled to 0°C. 1,8-diazabicyclo[5.4.0]undec-7-ene (5.08 mL, 34.0 mmol) and 2,2,2-trifluoro-N-phenyliminoacetyl chloride (5.25 mL, 31.1 mmol) were added under nitrogen atmosphere at the same temperature and stirred for 5 hours. The reaction solution was filtered through a neutral silicone mat filled with dichloromethane (silicone 60N, manufactured by Kanto Chemical, particle size: 40–50 μm, 130 g). The silicone pad was washed with 10% ethyl acetate / dichloromethane (1760 mL, 220 mL aliquots each time). The main fraction was concentrated under reduced pressure, and toluene (228 mL) was added and concentrated to 97.5 mL under reduced pressure to obtain a toluene solution of 2-O-acetylglucan-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-3-O-[(naphthyl-2-yl)methyl]-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-1-O-(2,2,2-trifluoro-N-phenylacetylino)-D-glucose pyranose (the compound represented by formula A-7). Use this solution directly in the next step. 1 H-NMR (CDCl) 3) σ 7.85 - 7.80 (m, 1H), 7.78 (d, J = 8.6 Hz, 1H), 7.72 (s, 1H), 7.70 - 7.64 (m, 3H), 7.50 - 7.43 (m, 4H), 7.39 (dd, J = 8.6, 1.7 Hz, 1H), 7.33 - 7.08 (m, 30H), 7.06 - 7.01 (m, 1H), 6.88 (d, J = 6.9 Hz, 2H), 6.70 - 6.60 (m, 4H), 5.35 (dd, J = 2.9, 1.7 Hz, 1H), 4.97 - 4.88 (m, 4H), 4.84 (d, J = 13.2 Hz, 1H), 4.79 (d, J = 10.9 Hz, 1H), 4.65 - 4.49 (m, 7H), 4.43 (dd, J = 11.5, 4.0 Hz, 1H), 4.36 (dd, J = 12.0, 7.4 Hz, 1H), 4.22 (d, J = 11.5 Hz, 1H), 4.11 - 4.04 (m, 1H), 3.93 (dd, J = 9.7, 9.7 Hz, 1H), 3.89 - 3.83 (m, 2H), 3.82 - 3.69 (m, 4H), 3.64 (dd, J = 10.9, 4.0 Hz, 1H), 3.52 (dd, J = 10.9, 1.1 Hz, 1H), 3.39 (dd, J = 9.7, 2.9 Hz, 1H), 3.33 - 3.28 (m, 1H), 1.89 (s, 3H). 13 C-NMR (CDCl 3) σ 170.0, 167.4, 143.0, 138.8, 138.7, 138.5, 138.4, 138.0, 137.6, 135.6, 133.7, 133.2, 133.0, 131.5, 128.56, 128.53, 128.4, 128.32, 128.30, 128.26, 128.22, 128.19, 128.14, 128.12, 127.90, 127.86, 127.81, 127.74, 127.72, 127.69, 127.54, 127.46, 127.38, 127.28, 127.0, 126.3, 126.2, 126.0, 125.6, 124.3, 123.3, 119.3, 101.8, 98.2, 82.6, 79.0, 77.8, 76.2, 75.5, 75.0, 74.91, 74.89, 74.7, 74.5, 74.3, 74.1, 74.0, 73.4, 73.3, 71.7, 71.7, 71.3, 68.8, 68.3, 68.0, 67.0, 54.7, 20.8. HRMS(ESI + )[M+HNH 3] + C 96 H 91 F 3N 3O 18 + Calculated value: 1635.6591; Experimental value: 1635.6549. [α] D 20 =+62.169(c 1.002,CDCl 3). Implementation Example 25 [Chemical Engineering 227] A toluene solution of 2-O-acetylglucosinolate-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-3-O-[(naphth-2-yl)methyl]-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-1-O-(2,2,2-trifluoro-N-phenylacetylino)-D-glucose pyranose (the compound represented by formula A-7) obtained in Example 24, and toluene (488 21.55 g (36.2 mmol) of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (represented by formula A-8) was added to a 1 L 4-bore flask, and molecular sieve 4A powder (14.6 g) was added. Trimethylsilane trifluoromethanesulfonate (545 μL, 2.83 mmol) was added dropwise at -15 °C for 5 minutes under nitrogen atmosphere, and the mixture was stirred at the same temperature for 1 hour. After confirming the completion of the reaction by HPLC, triethylamine (1.67 mL, 11.32 mmol) was added, and the mixture was heated to room temperature. The reaction solution was filtered and washed with acetonitrile (160 mL). The filtrate was concentrated to 97.5 mL under reduced pressure, and acetonitrile (650 mL) was added, followed by further concentration to 97.5 mL under reduced pressure. Add acetonitrile (488 mL) and reverse-phase silica gel 120RP-18 (manufactured by Kanto Chemical, particle size 40–50 μm, 130 g). Add water (146 mL) dropwise over 30 minutes to adsorb the target compound onto the solid phase, then filter. Wash with acetonitrile (536 mL)-water (146 mL) (filtrate discarded), and desorb the target compound using acetonitrile (975 mL)-ethyl acetate (244 mL). Concentrate the filtrate under reduced pressure, and perform two azeotropic distillations with toluene (325 mL) to achieve a final volume of 97.5%. mL, thereby obtaining a toluene solution of 4-methoxyphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-3-O-[(naphthyl-2-yl)methyl]-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula A-9). Take a portion of this solution (90 mL, based on the compound represented by formula A-4: 26.1 mmol) for the next step. 1H-NMR(CDCl 3) σ 7.86 - 7.81 (m, 1H), 7.81 - 7.75 (m, 2H), 7.74 - 7.60 (m, 7H), 7.56 - 7.44 (m, 5H), 7.40 (dd, J = 8.6, 1.1 Hz, 1H), 7.28 - 7.05 (m, 35H), 6.95 - 6.91 (m, 2H), 6.91 - 6.88 (m, 2H), 6.78 - 6.62 (m, 8H), 6.61 - 6.55 (m, 2H), 5.42 (d, J = 8.6 Hz, 1H), 5.33 (dd, J = 2.9, 1.7 Hz, 1H), 5.23 (d, J = 8.0 Hz, 1H), 4.98 (d, J = 12.6 Hz, 1H), 4.94 - 4.85 (m, 4H), 4.82 (d, J = 13.2 Hz, 1H), 4.76 (d, J = 10.9 Hz, 1H), 4.65 - 4.29 (m, 16H), 4.25 - 4.12 (m, 5H), 4.04 (dd, J = 10.3, 8.0 Hz, 1H), 3.95 (dd, J = 9.2, 9.2 Hz, 1H), 3.89 - 3.80 (m, 3H), 3.77 (d, J = 9.2 Hz, 1H), 3.73 (d, J = 10.9 Hz, 1H), 3.70 - 3.65 (m, 1H), 3.64 (s, 3H), 3.63 - 3.57 (m, 2H), 3.53 - 3.46 (m, 2H), 3.44 - 3.35 (m, 4H), 3.30 - 3.23 (m, 2H), 1.83 (s, 3H). 13 C-NMR (CDCl 3) σ 169.8, 168.1, 167.4, 155.2, 150.8, 138.9, 138.71, 138.68, 138.55, 138.48, 138.36, 137.9, 135.6, 133.8, 133.6, 133.2, 133.0, 131.8, 131.6, 131.5, 128.5, 128.34, 128.32, 128.29, 128.26, 128.20, 128.17, 128.12, 128.10, 127.89, 127.85, 127.80, 127.77, 127.69, 127.65, 127.52, 127.47, 127.44, 127.36, 127.29, 127.28, 126.90, 126.87, 126.3, 126.2, 126.0, 125.7, 123.5, 123.2, 123.1, 118.5, 114.2, 102.1, 98.2, 97.4, 97.1, 82.7, 80.0, 77.8, 76.6, 75.9, 74.9, 74.8, 74.63, 74.61, 74.56, 74.49, HRMS(ESI) + )[M+HNEt 3] + C 129 H 134 N 3O 25 + Calculated value: 2125.9334; Experimental value: 2125.9267. [α] D 20 =+30.098(c 1.008, CDCl 3). Implementation Example 26 [Chemical Engineering 228] A toluene solution (90 mL, compound A-4 reference: 26.1) of 4-methoxyphenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-3-O-[(naphthyl-2-yl)methyl]-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (compound represented by formula A-9) obtained in Example 25 was prepared. Add 1 mmol) of tetrahydrofuran (165 mL), methanol (75 mL), and methyl trifluoroacetate (2.76 mL, 27.8 mmol) to a 1 L 4-inch flask. Add tetrahydrofuran (13.9 mL, 13.9 mmol), methanol (75 mL), and methyl trifluoroacetate (2.76 mL, 27.8 mmol) at room temperature under nitrogen. After stirring for 5 minutes, add 1 M potassium tert-butoxide solution in tetrahydrofuran (13.9 mL, 13.9 mmol) and stir at 40 °C for 1 hour. After confirming the completion of the reaction by HPLC, cool to room temperature. Add acetic acid (1.11 mL, 19.4 mmol), then add ethyl acetate (330 mL) and water (270 mL). Add triethylamine to pH 7, then add sodium chloride (2.7 g) and stir for 5 minutes. After standing, separate the layers and wash the obtained organic layer twice with water (270 mL). Concentrate the organic layer to 90 mL under reduced pressure, add toluene (300 mL), concentrate again to 90 mL under reduced pressure, add toluene (300 mL), and concentrate again to 90 mL under reduced pressure. mL, thereby obtaining a toluene solution of 4-methoxyphenyl 3,4,6-tris-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-3-O-[(naphthyl-2-yl)methyl]-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula A-10). The solution was used directly in the next step. 1 H-NMR (CDCl) 3) σ 7.85 - 7.81 (m, 1H), 7.79 (d, J = 8.6 Hz, 1H), 7.78 - 7.72 (m, 2H), 7.72 - 7.60 (m, 6H), 7.59 - 7.54 (m, 1H), 7.50 - 7.44 (m, 4H), 7.41 (dd, J = 8.6, 1.1 Hz, 1H), 7.31 - 7.13 (m, 32H), 7.10 - 7.05 (m, 2H), 6.97 - 6.93 (m, 2H), 6.90 - 6.86 (m, 2H), 6.78 - 6.67 (m, 8H), 6.61 - 6.56 (m, 2H), 5.43 (d, J = 8.6 Hz, 1H), 5.25 (d, J = 8.0 Hz, 1H), 4.99 - 4.86 (m, 4H), 4.83 (d, J = 12.6 Hz, 1H), 4.71 (d, J = 10.9 Hz, 1H), 4.64 (d, J = 12.0 Hz, 1H), 4.61 (d, J = 12.0 Hz, 1H), 4.56 (d, J = 6.9 Hz, 1H), 4.53 - 4.39 (m, 7H), 4.39 - 4.31 (m, 5H), 4.30 (d, J = 11.5 Hz, 1H), 4.25 - 4.14 (m, 4H), 4.05 (dd, J = 9.7, 8.6 Hz, 1H), 3.94 - 3.88 (m, 2H), 3.86 - 3.80 (m, 2H), 3.76 - 3.68 (m, 3H), 3.68 - 3.59 (m, 5H), 3.57 - 3.35 (m, 7H), 3.31 - 3.25 (m, 2H), 2.15 (d, J = 4.0 Hz, 1H). 13 C-NMR (CDCl 3) σ 168.2, 167.5, 155.2, 150.8, 138.91, 138.88, 138.6, 138.52, 138.47, 138.38, 128.32, 128.0, 137.9, 135.7, 133.9, 133.6, 133.3, 133.0, 131.8, 131.6, 131.4, 128.5, 128.29, 128.23, 128.19, 128.13, 128.0, 127.92, 127.87, 127.82, 127.79, 127.76, 127.70, 127.56, 127.53, 127.46, 127.36, 127.31, 127.28, 126.9, 126.3, 126.2, 126.0, 125.7, 123.5, 123.2, 123.1, 118.6, 114.2, 101.9, 99.7, 97.4, 97.1, 82.7, 79.7, 79.6, 76.7, 75.9, 75.3, 74.9, 74.8, 74.73, 74.68, 74.63, 74.5, 74.4, 74.2, 74.1, 73.2, 73.2, 72.6, 71.8, 71.3, 71.2, 68.9, 68.13, 68.07, 67.8, 66.6, 56.5, 55.6, 55.5. HRMS(ESI + )[M+HNEt 3] + C 127 H 132 N 3O 24 + Calculated value: 2083.9229; Experimental value: 2083.9150. [α] D 20 =+27.776(c 1.007, CDCl 3). Implementation Example 27 [Chemistry 229] In a toluene solution of 4-methoxyphenyl 3,4,6-tris-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-3-O-[(naphthyl-2-yl)methyl]-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula A-10) obtained in Example 26, dichloromethane (450 A toluene solution (118.2 g, 36.2 mmol) of 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-1-O-(2,2,2-trifluoro-N-phenylacetylimino)-β-D-glucopyranose (represented by formula A-11) was added to a 1 L 4-bore flask, and molecular sieve 4A powder (below 10 μm, 15.0 g) was added. Tributyl dimethyl silane trifluoromethanesulfonate (2.4 mL, 10.4 mmol) was added dropwise at -78°C for 5 minutes under nitrogen atmosphere, and the mixture was stirred at the same temperature for 10 hours. Triethylamine (4.6 mL, 33.2 mmol) was added, and the mixture was heated to room temperature. The reaction solution was filtered through diatomaceous earth and washed with acetonitrile (150 mL). The filtrate was concentrated to 150 mL under reduced pressure, and acetonitrile (600 mL) was added, followed by further concentration to 150 mL under reduced pressure. Acetonitrile (600 mL) and silicone 120RP-18 (manufactured by Kanto Chemical, particle size: 40–50 μm, 135 g) for reverse phase were added. Water (120 mL) was added dropwise over 30 minutes to allow the target analyte to adsorb onto the solid phase, followed by filtration. The solid phase was washed with acetonitrile (900 mL)-water (135 mL) (the washing solution was discarded), and the target analyte was desorbed from the solid phase using an acetonitrile (840 mL)-ethyl acetate (210 mL) solution.The eluent was concentrated under reduced pressure, and toluene (300 mL) was added. The solution was then concentrated to 90 mL under reduced pressure to obtain 4-methoxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranose-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-3-O-[(naphthyl-2-yl)] A toluene solution of [methyl]-β-D-mannopyranoside-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula A-12). The solution is used directly in the next step. 1 H-NMR (CDCl) 3) σ 7.84 - 7.73 (m, 4H), 7.70 - 7.57 (7H), 7.55 - 7.03 (m, 68H), 6.99 - 6.89 (m, 11H), 6.88 - 6.83 (m, 1H), 6.82 - 6.67 (m, 7H), 6.67 - 6.62 (m, 2H), 6.62 - 6.56 (m, 3H), 5.42 (d, J = 8.6 Hz, 1H), 5.23 (d, J = 8.6 Hz, 1H), 5.02 (d, J = 8.6 Hz, 1H), 4.95 - 4.89 (m, 3H), 4.86 - 4.79 (m, 5H), 4.77 - 4.66 (m, 4H), 4.64 - 4.08 (m, 30H), 4.06 - 3.98 (m, 3H), 3.91 - 3.68 (m, 9H), 3.65 (s, 3H), 3.58 (d, J = Hz, 1H), 3.54 - 3.32 (m, 13H), 3.32 - 3.27 (m, 1H), 3.22 - 3.16 (m, 3H), 2.84 (dd, J = 10.9, 5.7 Hz, 1H). 13 C-NMR (CDCl) 3) σ 168.4, 168.2, 167.4, 155.2, 150.8, 139.1, 139.02, 139.99, 138.93, 138.8, 138.7, 138.52, 138.48, 138.38, 138.32, 138.06, 138.01, 135.6, 133.7, 133.61, 133.56, 133.3, 133.2, 132.9, 131.8, 131.6, 131.4, 128.54, 128.50, 128.39, 128.34, 128.17, 128.13, 128.10, 128.00, 127.96, 127.89, 127.82, 127.78, 127.67, 127.64, 127.62, 127.59, 127.51, 127.48, 127.46, 127.41, 127.39, 127.29, 127.20, 127.05, 127.01, 126.9, 126.7, 126.3, 126.2, 125.9, 125.7, 123.5, 123.2, 123.1, 123.0, 118.6, 114.2, 102.9, 102.7, 97.8, 97.4, 97.0, 96.9, 83.1, 82.5, 80.4, 79.9, 77.7, 77.4, 76.9, 76.6, 75.7, 75.3, 75.1, 75.0, 74.8, 74.7, 74.6, 74.52, 74.46, 74.0, 73.95, 73.85, 73.7, 73.4, 73.2, 73.0, 72.9, 72.58, 72.55, 72.52, 72.48, 72.0, 71.9, 69.8, 69.7, 68.2, 3, 68.20, 68.06, 68.03, 67.0, 56.6, 55.6, 55.5 HRMS(ESI + )[M+HNEt 3] + C 191 H 175 N 4O 35 + Calculated value: 3078.3350; Experimental value: 3078.3200. [α] D 20 =+9.276(c 1.002,CDCl 3). Example 28-1 [Chemical 230] The 4-methoxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyrano-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyrano-(1→6)-2,4-di-O-benzyl-3-O-[(naphthyl-2-yl)] obtained in Example 27 A toluene solution (equivalent to 64.2 mmol) of methyl]-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (represented by formula A-12) was added to a 3L 4-bore flask, followed by the addition of 1,1,1,3,3,3-hexafluoro-2-propanol (1337 mL) and water (133.7 mL). After cooling the reaction solution to approximately -30°C, 17.48 g (77.0 mmol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone was added and the mixture was stirred for 38 hours. Once the reaction was confirmed to be complete, a sodium sulfite (4.04 g, 32.1 mmol)-water (95.6 mL) solution was added to terminate the reaction, and the mixture was heated to room temperature over 1 hour. Dichloromethane (1910 mL) and sodium bicarbonate (38.2 g)-sodium sulfite (38.2 g)-water (1910 mL) solutions were added separately and stirred for 5 minutes. After standing, the mixture was separated, and the organic layer was concentrated to 573 mL under reduced pressure. Toluene (955 mL) was added to the residue, and the mixture was concentrated to 573 mL under reduced pressure. Ethyl acetate (955 mL) and sodium chloride (95.5 g)-water (860 mL) solutions were added and stirred for 5 minutes. After settling, the liquid was separated. The organic layer was concentrated to 382 mL under reduced pressure, and acetonitrile (1910 mL) was added. The solution was then concentrated again to 382 mL under reduced pressure. Acetonitrile (1528 mL) and silicone 120RP-18 (manufactured by Kanto Chemical, particle size 40–50 μm, 573 g) for reverse phase mixing were added to the residue. Water (1242 mL) was added dropwise over 30 minutes to allow the target analyte to adsorb onto the solid phase, followed by filtration. The solid phase was washed with acetonitrile (1337 mL)-water (573 mL) (the washing solution was discarded), and then washed with methanol (955 mL). Subsequently, the target analyte was desorbed from the solid phase using an acetonitrile (6876 mL)-tetrahydrofuran (764 mL) solution.The eluent was concentrated under reduced pressure and then dried to obtain the crude product 4-methoxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranose-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4 -Di-O-benzyl-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (compound represented by formula A-13) 167 g. The crude product was purified by fractional HPLC to obtain 4-methoxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranose-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)- 2,4-Di-O-benzyl-β-D-mannopyranose-(1→4)-3,6-Di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula A-13) 96 g (gross yield of the compound represented by formula C-13 is 36.1%). 1 H-NMR (CDCl) 3) σ 7.75 (d, J = 8.0 Hz, 1H), 7.69 - 7.40 (10H), 7.55 - 7.10 (m, 54H), 7.06 - 6.97(5H), 6.97 - 6.89 (m, 8H), 6.88 - 6.84 (m, 1H), 6.82 - 6.73 (m, 5H), 6.72 - 6.67 (m, 2H), 6.62 - 6.56 (m, 5H), 5.42 (d, J = 8.6 Hz, 1H), 5.22 (d, J = 8.0 Hz, 1H), 5.03 (d, J = 12.0 Hz, 1H), 4.99 (d, J = 8.6 Hz, 1H), 4.92 (d, J = 10.9 Hz, 1H), 4.87 - 4.79 (m, 5H), 4.75 (d, J = 11.5 Hz, 1H), 4.70 (d, J = 12.0 Hz, 1H), 4.67 (d, J = 12.0 Hz, 1H), 4.63 (d, J = 6.3 Hz, 1H), 4.61 (d, J = 6.9 Hz, 1H), 4.60 - 3.97 (m, 30H), 3.88 (d, J = 2.9 Hz, 1H), 3.84 (d, J = 12.0 Hz, 1H), 3.82 - 3.67 (m, 5H), 3.66 - 3.60 (m, 5H), 3.54 - 3.33 (m, 14H), 3.27 - 3.23 (m, 1H), 3.20 (d, J = 10.9 Hz, 1H), 3.15 - 3.09 (m, 2H), 2.83 - 2.78 (m, 1H), 2.27 - 2.21 (m, 1H). 13 C-NMR(CDCl 3) σ 168.4, 168.2, 167.4, 167.3, 155.2, 150.8, 139.1, 139.0, 138.9, 138.8, 138.7, 138.51, 138.49, 138.44, 138.38, 138.37, 138.35, 138.26, 138.0, 137.7, 133.8, 133.6, 122.49, 133.41, 133.36, 131.8, 131.4, 128.6, 128.52, 128.49, 128.39, 128.34, 128.30, 128.2, 128.14, 128.10, 128.06, 128.0, 127.85, 127.82, 127.7, 127.69, 127.65, 127.56, 127.53, 127.48, 127.38, 127.33, 127.26, 127.1, 127.0, 126.9, 126.7, 123.5, 123.2, 123.09, 123.05, 122.98, 118.5, 114.2, 102.9, 102.6, 97.8, 97.4, 97.0, 96.9, 82.5, 80.5, 79.9, 78.5, 77.8, 77.4, 76.9, 76.7, 75.87, 75.80, 75.2, 75.0, 74.79, 74.77, 74.62, 74.59, 74.48, 74.41, 74.2, 74.0, 73.9, 73.6, 73.4, 73.0, 72.9, 72.7, 72.62, 72.56, 72.0, 69.8, 68.24, 68.20, 68.1, 67.8, 67.2, 56.6, 55.6, 55.5, 53.4. HRMS (ESI) + )[M+HNEt 3] + C 172 H 183 N 4O 35 + Calculated value: 2938.2725; Experimental value: 2938.2516. [α] D 20 =+14.385(c 1.005, CDCl 3). Example 28-2: The compound represented by formula A-13 was purified using a method based on the following procedure. As shown below, this purification method allows for the acquisition of the compound represented by formula A-13 in high purity without HPLC separation purification. [Chemical 231] Methoxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(2-carboxybenzophenamine)-β-D-glucopyranose-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-β-D-mannopyranose-( Synthesis of (1→4)-3,6-di-O-benzyl-2-deoxy-2-(2-carboxybenzophenamine)-β-D-glucopyranoside (1→4)-3,6-di-O-benzyl-2-deoxy-2-(2-carboxybenzophenamine)-β-D-glucopyranoside tri(R)-(+)-1-(1-naphthyl)ethylamine salt (the compound represented by formula A-14) [Chemistry 232] 4-Methoxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranose-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-β-D-pyranose Mannose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (compound represented by formula A-13) (25.00) 8.82 mmol (72.2 PA%) g of silica gel was dissolved in dichloromethane (250 mL). The silica gel (62.5 g, Chromatorex SMB100-20 / 45 manufactured by Fuji Silysia) was then passed through the solvent. Dissolution was performed using a diisopropyl ether / dichloromethane mixed solvent (7 / 93, 1000 mL) (125 mL fractions were distilled during both the passing and dissolution operations, and the solution was recovered). Purity was determined by HPLC, and the selected fractions were mixed and concentrated to 38 mL. Tetrahydrofuran (125 mL) was added to the concentrate, and after concentrating to 38 mL, tetrahydrofuran (100 mL), methanol (38 mL), and sodium hydroxide aqueous solution (4 M, 16.5 mL, 7.5 equivalents) were added dropwise. The mixture was heated to 45 °C and stirred for 1 hour. After confirming the reaction was complete, the mixture was cooled to 0°C and neutralized by adding hydrochloric acid (6 M, 11 mL, 7.5 equivalents) dropwise at below 10°C. Ethyl acetate (250 mL) and 3% saline solution (250 mL) were added, and the pH of the aqueous layer was adjusted to below 2.0 with hydrochloric acid (6 M) while stirring. The aqueous layer was removed by separation, and the obtained organic layer was washed with 3% saline solution (250 mL). The organic layer was concentrated to 38 mL, and ethyl acetate (250 mL) was added and concentrated to 38 mL. Ethyl acetate (138 mL), (R)-(+)-1-(1-naphthyl)ethylamine (5.28 g, 3.5 equivalents), and seed crystals (0.03 g) were added to the concentrate. The mixture was stirred at 25°C for at least 12 hours and then cooled to 0°C. Heptane (88 mL) was added dropwise over 1 hour, and the mixture was stirred for 2 hours. The precipitated crystals were then filtered to obtain wet crystals (purity 92.9 PA%). Ethyl acetate (125 mL) was added to the obtained wet crystals, and the mixture was stirred at 35°C for 30 minutes. The mixture was then cooled to 25°C and stirred for 12 hours. The slurry was cooled to 0°C over 1 hour, and heptane (75 mL) was added dropwise over a period of more than 1 hour.After stirring at 0°C for 2 hours, the precipitated crystals were filtered and dried under reduced pressure to obtain 4-methoxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(2-carboxybenzophenamine)-β-D-glucopyranose-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6) )-2,4-di-O-benzyl-β-D-mannopyranose-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(2-carboxybenzoylamine)-β-D-glucopyranoside tri(R)-(+)-1-(1-naphthyl)ethylamine salt (the compound represented by formula A-14) (18.93 g, yield 63.1%, purity 97.2 PA%). The powder X-ray crystallization analysis of the obtained crystals is shown below. <Measuring Instrument> Powder X-ray crystallography analysis apparatus: Rigaku <Measurement Conditions> Wavelength: Cuka / 1.541862 Å Goniometer: MiniFlex 300 / 600 Scan speed: CONTINUOUS Scan speed / counting time: 10.00 Step size: 0.02 deg Scan axis: 2θ / θ Scan range: 3.00~40.00 deg Filter: K-beta (×1) Rotation: <Powder X-ray crystallography analysis line graph of compound A-14> [Chem. 233] The transformation from the compound represented by formula A-14 to the compound represented by formula A-13 [Chemistry 234] 4-Methoxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(2-carboxybenzophenamine)-β-D-glucopyranose-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2,4-di-O-benzyl-β-D-mannopyranose 18.00 g of glycoside (1→4)-3,6-di-O-benzyl-2-deoxy-2-(2-carboxybenzoxylamine)-β-D-glucopyranoside (1→4)-3,6-di-O-benzyl-2-deoxy-2-(2-carboxybenzoxylamine)-β-D-glucopyranoside tri(R)-(+)-1-(1-naphthyl)ethylamine salt (represented by formula A-14) (90 mL) was added to cyclopentyl methyl ether. The mixture was washed three times with 1 M hydrochloric acid aqueous solution (180 mL) and then with 5% saline solution (90 mL). The resulting organic layer was concentrated to 18 mL, and cyclopentyl methyl ether (90 mL) was added. The mixture was then concentrated to 18 mL under reduced pressure. Add tetrahydrofuran (90 mL) and carbonyl diimidazole (6.86 g, 8 equivalents) to the concentrate. Stir at 35°C for 1 hour to confirm the completion of the reaction (except for the ring-closing reaction of phthalimide, confirming the product after the imidazole carbonylation of the hydroxyl group). Add water (9 mL) and trifluoroacetic acid (12.1 g, 20 equivalents). Heat to 60°C and stir for 20 hours to confirm the deimidazole carbonylation. Cool to room temperature. Add ethyl acetate (90 mL) and water (90 mL) and separate the layers. Wash the organic layer sequentially with 5% sodium bicarbonate solution (90 mL) and water (90 mL). Concentrate the obtained organic layer to 18 mL under reduced pressure. Add toluene (90 mL), concentrate to 18 mL, and then add dichloromethane (162 mL). The dichloromethane solution was passed through silicone (36 g, Chromatorex SMB100-20 / 45 manufactured by Fuji Silysia). Dissolution was performed using a diisopropyl ether / dichloromethane mixed solvent (7 / 93, 720 mL) (90 mL fractions were distilled during both the passing and dissolution processes, and the solution was recovered). The purity of the fraction was determined by HPLC, and the selected fractions were mixed and concentrated to 18 mL. Cyclopentyl methyl ether (90 mL) was added to the concentrate, and the solution was concentrated to 36 mL. Then, the solution was added dropwise over a stirring period of at least 30 minutes to isopropanol (630 mL) cooled to 0°C.After stirring at 0°C for 2 hours, the slurry was filtered, washed with isopropanol (180 mL) at 0°C, and the resulting powder was dried under reduced pressure to obtain 4-methoxyphenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranose-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranose-(1→6)-2 ,4-Di-O-benzyl-β-D-mannopyranose-(1→4)-3,6-Di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside-(1→4)-3,6-Di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula A-13) (14.1 g, yield 93%, purity 97.0 PA%). [Analytical Conditions] Column: Xbridge phenyl 3.5 μm, 4.6 ×150 mm (Waters) Wavelength: 220 nm Oven: 40℃ Dissolution solution: (A) 10 mM AcONH 4. Aqueous solution, (B) acetonitrile gradient: 0 min (B) concentration 85% 30 min (B) concentration 100% 30.01 min (B) concentration 85% 35 min (B) concentration 85% Flow rate: 1 mL / min Injection: 5 μL HRMS (ESI) + )[M+NH 4] + C 172 H 168 N 3O 35 Calculated value: 2852.1718; Experimental value: 2852.1694 1 H-NMR (500 MHz, CDCl 3) δ σ 7.75 (d, J = 8.0 Hz, 1H), 7.69 - 7.40 (10H), 7.55 - 7.10 (m, 54H), 7.06 - 6.97 (5H), 6.97 - 6.89 (m, 8H), 6.88 - 6.84 (m, 1H), 6.82 - 6.73 (m, 5H), 6.72 - 6.67 (m, 2H), 6.62 - 6.56 (m, 5H), 5.42 (d, J = 8.6 Hz, 1H), 5.22 (d, J = 8.0 Hz, 1H), 5.03 (d, J = 12.0 Hz, 1H), 4.99 (d, J = 8.6 Hz, 1H), 4.92 (d, J = 10.9 Hz, 1H), 4.87 - 4.79 (m, 5H), 4.75 (d, J = 11.5 Hz, 1H), 4.70 (d, J = 12.0 Hz, 1H), 4.67 (d, J = 12.0 Hz, 1H), 4.63 (d, J = 6.3 Hz, 1H), 4.61 (d, J = 6.9 Hz, 1H), 4.60 - 3.97 (m, 30H), 3.88 (d, J = 2.9 Hz, 1H), 3.84 (d, J = 12.0 Hz, 1H), 3.82 - 3.67 (m, 5H), 3.66 - 3.60 (m, 5H), 3.54 - 3.33 (m, 14H), 3.27 - 3.23 (m, 1H), 3.20 (d, J = 10.9 Hz, 1H), 3.15 - 3.09 (m, 2H), 2.83 - 2.78 (m, 1H), 2.27 - 2.21 (m, 1H) 13 C-NMR (125 MHz, CDCl 3) δ 168.4, 168.2, 167.4, 167.3, 155.2, 150.8, 139.1, 139.0, 138.9, 138.8, 138.7, 138.51, 138.49, 138.44, 138.38, 138.37, 138.35, 138.26, 138.0, 137.7, 133.8, 133.6, 122.49, 133.41, 133.36, 131.8, 131.4, 128.6, 128.52, 128.49, 128.39, 128.34, 128.30, 128.2, 128.14, 128.10, 128.06, 128.0, 127.85, 127.82, 127.7, 127.69, 127.65, 127.56, 127.53, 127.48, 127.38, 127.33, 127.26, 127.1, 127.0, 126.9, 126.7, 123.5, 123.2, 123.09, 123.05, 122.98, 118.5, 114.2, 102.9, 102.6, 97.8, 97.4, 97.0, 96.9, 82.5, 80.5, 79.9, 78.5, 77.8, 77.4, 76.9, 76.7, 75.87, 75.80, 75.2, 75.0, 74.79, 74.77, 74.62, 74.59, 74.48, 74.41, 74.2, 74.0, 73.9, 73.6, 73.4, 73.0, 72.9, 72.7, 72.62, 72.56, 72.0, 69.8, 68.24, 68.20, 68.1, 67.8, 67.2, 56.6, 55.6, 55.5, 53.4 Example 29 Regarding the desylation reaction of the compound represented by formula C-8 in Example 15 above, and the compound represented by formula C-9, a comparative experiment was conducted using the reaction conditions shown in the table below. Items 1-3 are comparative examples, and items 4 and 5 are embodiments of the present invention. [Chemistry 235] [Table 1] • If NaOMe is used, the ring-opening reaction proceeds completely due to the influence of moisture in the reagent (Item 1). • Under acidic conditions, although the ring-opening of the phthalimide group can be inhibited, the reaction rate is slow and decomposition occurs (Item 2). • When using t-BuOK, approximately 85% of the target compound is formed, but approximately 8% of the ring-opening compound is formed as a byproduct due to the influence of moisture in the reagent and solvent (Item 3). • CF was added. 3CO At 2Me, the reaction almost completely inhibits the ring-opening phase and ends. t-BuOK and LHMDS, as bases, yielded similar results (items 4 and 5). Example 30 The de-2-naphthylmethylation reaction of a compound represented by formula A-12, containing 15 benzyl groups and 1 2-naphthylmethyl group, was carried out as shown in the table below, under the previous conditions (CH 2Cl 2-H 2O)(Project 1) and the method of the present invention (HFIP-H) The analysis was performed using HPLC (Projects 2 and 3) to calculate the peak area ratio of the target compound (represented by Formula A-13) and the debenzylated matrix as the excess reactant. The results are shown in the table below. [Chemistry 236] [Table 2] • Item 1 showed moderate selectivity with the debenzylidene matrix under the conditions of the previous method. • Item 2 showed improved selectivity by using HFIP. • Item 3 achieved the best results by using HFIP at further low temperatures. Example 31: De-2-naphthylmethylation of the compound represented by formula A-4, which contains four benzyl groups and one 2-naphthylmethyl group, is shown in the table below, based on previous conditions (CH). 2Cl 2-H 2O)(Project 1), Method of the Invention (HFIP-H) The reaction was carried out under 2O (Item 2), acidic conditions (Item 3), and hydrogenation conditions (Item 4). The area ratio of the target compound (represented by Formula A-4' below) was calculated by HPLC analysis. The results are shown in the table below. [Chemistry 237] [Table 3] • Project 1: The reaction proceeded in moderate to high yields under the conditions of the previous method. • Project 2: The reaction was further improved by using HFIP. • Project 3: The HCl / HFIP conditions reported in the paper (J. Org. Chem. 2015, 80, 8796-8806) were applied, but the reaction became more complicated, resulting in low yields. • Project 4: De-benzyl group desorption was also observed when hydrogenation conditions were used, resulting in low yields. Example 32: De-2-naphthylmethylation of the compound represented by formula A-10, which contains 9 benzyl groups and 1 2-naphthylmethyl group, as shown in the table below, based on previous conditions (CH). 2Cl 2-H 2O)(Project 1) and the method of the present invention (HFIP-H) The reaction was carried out in 2O)(Project 2), and the area ratio of the target compound (represented by formula A-10' below) was calculated by HPLC analysis. The results are shown in the table below. [Chemistry 238] [Table 4] Example 33 <Separation and Purification of Compounds Represented by Formula A-8 and Formula A-9> The following examples illustrate the separation and purification of the sugar acceptors used in the synthesis of tetrasaccharides, namely the compounds represented by Formula A-8 and Formula A-9. The compounds represented by Formula A-8, as sugar acceptors, and the compounds represented by Formula A-9, as tetrasaccharides, exhibit very similar polarities in cis-phase silicone column chromatography, for example, having the same Rf value under hexane-ethyl acetate conditions, a typical column solvent system, making separation difficult. By utilizing the invention of this invention, monosaccharides and tetrasaccharides with very similar polarities can be easily separated in silicone. The experimental procedure is as follows. First, after the reaction, triethylamine was added to the solution to terminate the reaction, followed by filtration through a molecular sieve, concentration, and then addition of acetonitrile. Octadecyl-modified silica gel was added to the solution, followed by water to adsorb the compound represented by formula A-9 (a tetrasaccharide). HPLC analysis of the filtrate showed that the compound represented by formula A-9 (a tetrasaccharide) was adsorbed, and thus the compound represented by formula A-8 (a monosaccharide) remained in the filtrate. After washing with any amount of acetonitrile-water, the compound represented by formula A-8 (a tetrasaccharide) was extracted using acetonitrile and toluene. The purification results for the compound represented by formula A-8 are shown in Tables 1 and 2 below. [Chemistry 239] [Table 5] <Synthesis of the Compound Represented by Formula D-3> The compound represented by formula D-3 was synthesized according to the following synthetic procedure Z. [Synthetic Procedure Z] [Chemistry 240] Example 34 4-Methoxyphenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (compound represented by formula F-1) [Chemical 241] (Step Z-1) To a solution of 50.0 g (83.94 mmol) of 4-methoxyphenyl 3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula A-8) in ethyl acetate (200 mL), triethylamine (11.04 g, 109.12 mmol), dimethylaminopyridine (0.31 g, 2.52 mmol), and acetic anhydride (11.10 g, 109.12 mmol) were added, and the mixture was stirred at 20 °C for 4 hours. After confirming the completion of the reaction by HPLC, ethanol (500 mL) and water (150 mL) were added dropwise. The slurry was stirred for 1 hour, and the precipitated crystals were filtered. The filtered crystals were washed with a mixture of ethanol and water (150 / 50 mL) and dried under reduced pressure at 40°C to obtain 4-methoxyphenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (represented by formula F-1) as white crystals (49.0 g, yield 91%). 1 H-NMR (500 MHz, CDCl) 3) δ 7.85 - 7.60 (m, 4H), 7.24 - 7.34 (m, 5H), 7.04 - 7.00 (m, 2H), 6.96 - 6.87 (m, 3H), 6.84 (dt, J = 9.0, 3.0 Hz, 2H), 6.67 (dt, J = 8.5, 2.5 Hz, 2H), 5.66 (t, J = 4.0 Hz, 1H), 5.22 - 5.18 (m, 1H), 4.64 (d, J = 12.0 Hz, 1H), 4.55 - 4.48 (m, 4H), 4.36 (d, J = 12.0 Hz, 1H), 3.90 - 3.84 (m, 1H), 3.68 (s, 3H), 3.68 - 3.64 (m, 2H), 1.98 (s, 3H). 13 C-NMR (125 MHz, CDCl) 3) δ 169.6, 155.3, 150.6, 137.8, 137.5, 133.9, 128.2, 128.0, 127.7, 127.7, 127.5, 127.4, 123.3, 118.4, 114.3, 97.4, 76.8, 73.9, 73.7, 73.5, 72.2, 69.4, 55.4, 55.3, 20.8. HRMS(ESI + [M+H] + C 37 H 36 NO Calculated value of 9: 638.2385; Experimental value: 638.2401. Example 35 4-O-acetylated-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-D-glucopyranoside (compound represented by formula F-2) [Chemical 242] (Step Z-2) At temperatures below 25°C, [bis(trifluoroacetoxy)iodide]benzene (46.3 g, 107.58 mmol) was added to a solution of 4-methoxyphenyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-β-D-glucopyranoside (the compound represented by formula F-1) (49.0 g, 76.84 mmol) in dichloromethane (392 mL), hexafluoro-2-propanol (245 mL), and water (25 mL). The mixture was stirred at the same temperature for 4 hours. After confirming the completion of the reaction by HPLC, ethyl acetate (1225 mL) was added, and the mixture was cooled in an ice bath. Then, water (490 mL) containing dissolved sodium bicarbonate (24.5 g) and sodium sulfite (24.5 g) was added, and the mixture was separated to obtain the organic layer. The obtained organic layer was washed again with 490 mL of water containing dissolved sodium bicarbonate (24.5 g) and sodium sulfite (24.5 g), and then washed with 20% saline solution (245 g). The obtained organic layer was concentrated to 490 mL under reduced pressure (crystallization was confirmed during concentration), and heptane (735 mL) was added dropwise. The obtained slurry was cooled to 0℃~5℃ and stirred at the same temperature for 1 hour. The precipitated crystals were then filtered. The filtered crystals were washed with a mixture of ethyl acetate and heptane (39 / 118 mL) at 0-5°C and dried under reduced pressure at 40°C to obtain 4-O-acetylglucanol (represented by formula F-2) as white crystals (37.5 g, yield 92%). 1 H-NMR (400 MHz, CDCl) 3) δ 7.71 - 7.65 (m, 4H), 7.34 - 7.26 (m, 5H), 7.01 - 6.87 (m, 5H), 5.36 (dd, J = 8.0, 8.0 Hz, 1H), 5.13 (dd, J = 8.4, 10.0 Hz, 1H), 4.59 (d, J = 12.4 Hz, 1H), 4.54 (s, 2H), 4.50 (dd, J = 8.4, 10.4 Hz, 1H), 4.33 (d, J = 12.4 Hz, 1H), 4.17 (dd, J = 8.4, 10.4 Hz, 1H), 3.79 (ddd, J = 8.4, 5.2, 4.8 Hz, 1H), 3.61 - 3.53 (m, 2H), 3.41 (d, J = 8.0 Hz, 1H), 1.93 (s, 3H). 13 C-NMR (100 MHz, CDCl) 3) δ 169.8, 168.1, 137.7, 137.7, 134.0, 131.6, 128.4, 128.2, 128.0, 127.8, 127.7, 127.5, 123.4, 116.2, 92.9, 73.9, 73.7, 73.5, 72.2, 69.3, 57.1, 20.9. HRMS(ESI - [MH] - C 30 H 28 NO Calculated value of 8: 530.1820; Experimental value: 530.1841. Example 36: 4-O-acetylated-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-O-[2,2,2-trifluoro-N-phenylacetylino]-β-D-glucopyranoside (the compound represented by formula D-3) [Chemical 243] (Step Z-3) 4-O-acetylated-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-D-glucopyranoside (the compound represented by formula F-2) (20.0 g, 37.63 mmol) was added to a 500 mL round-bottom flask, along with 200 mL of dichloromethane and 10.0 g of molecular sieve 4A powder (below 10 μm). Under nitrogen atmosphere and at 0 °C, N-methylimidazolium (3.40 g, 41.39 mmol) and 2,2,2-trifluoro-N-phenyliminoacetyl chloride (8.20 g, 39.51 mmol) were added sequentially, and the mixture was stirred at the same temperature for 18 hours. After confirming the reaction was complete by HPLC, the reaction solution was filtered and washed with 100 mL of dichloromethane. The filtrate was filtered through a neutral silicone pad filled with dichloromethane (Silicone 60N, manufactured by Kanto Chemical, particle size: 40–50 μm, 60 g), with 100 mL aliquots collected each time. The silicone pad was washed with dichloromethane (400 mL, 100 mL aliquots each time) and ethyl acetate / dichloromethane (1:4, 400 mL, 100 mL aliquots each time), and the selected fraction was concentrated to a volume of 40 mL. Add toluene (200 mL), concentrate again to a volume of 40 mL, then add toluene (200 mL) and concentrate again to a volume of 40 mL to obtain a toluene solution of the crude product 4-O-acetylated-3,6-di-O-benzyl-2-deoxy-2-(1,3-dioxy-1,3-dihydro-2H-isoindol-2-yl)-O-[2,2,2-trifluoro-N-phenylacetylino]-β-D-glucopyranoside (the compound represented by formula D-3). Use this solution directly in the next step. <Synthesis of the Compound Represented by Formula D-7> The compound represented by formula D-7 was synthesized according to the following synthetic procedure V. [Synthetic Procedure V] [Chemistry 244] First, the compound represented by formula G-1 was synthesized according to the following synthetic procedure W. [Synthetic Procedure W] [Chemistry 245] Example 37 Allyl α-D-galactofuranoside (compound represented by G-0) [Chemical 246] D-galactofuranose (20.00 g, 111.01 mmol) was added to a 500 mL four-necked flask, followed by allyl alcohol (200.0 mL). The reaction mixture was then added at room temperature under a nitrogen atmosphere to the TsOH·H₂O mixture. 2.11 g (11.10 mmol) of triethylamine was added and the mixture was heated to 70 °C and stirred for 24 hours. The reaction solution was cooled to 40 °C, and 1.69 g (16.65 mmol) of triethylamine was added and stirred for 5 minutes. The reaction solution was then concentrated under reduced pressure to a volume of 100 mL. 200 mL of nBuOH was added dropwise to the concentrate over 30 minutes and stirred at room temperature for 1 hour. The reaction solution was then concentrated under reduced pressure to a volume of 80 mL and stirred overnight at room temperature. The suspension was filtered, and the crystals were washed with 40 mL of nBuOH at 0 °C and dried under reduced pressure at 40 °C to obtain allyl α-D-galactofuranoside (represented by compound G-0) as white crystals (8.41 g, yield 34.4%). 1 H-NMR(500 MHz, METHANOL-D4) δ 5.97 (qd, J = 11.2, 5.7 Hz, 1H), 5.33 (dd, J = 17.2, 1.7 Hz, 1H), 5.17 (dd, J = 10.6, 1.4 Hz, 1H), 4.22 (dd, J = 13.2, 5.2 Hz, 1H), 4.04 (dd, J = 13.0, 6.0 Hz, 1H), 3.88 (d, J = 1.7 Hz, 1H), 3.82 - 3.66 (m, 5H). 13 C-NMR(125 MHz, METHANOL-D4) δ 62.74, 69.36, 70.21, 71.08, 71.51, 72.49, 99.46, 117.47, 135.69. MS(ESI)m / z: 221(M+H) + 219 (MH) - . Example 38 Prop-2-en-1-yl 4,6-O-benzyl-α-D-galactofuranoside (compound represented by formula G-1) [Chemical 247] Acetonitrile (5.0 mL), benzaldehyde dimethyl acetal (5.18 g, 34.1 mmol), and para-TsOH·H under a nitrogen atmosphere were added. 2O (431.9 mg, 2.27 mmol) was added to a 100 mL round-bottom flask, followed by the addition of allyl α-D-galactofuranoside (5.00 g, 22.7 mmol) dropwise. The solution was heated to 40 °C and stirred for 30 minutes. Then, triethylamine (344.6 mg, 3.41 mmol) was added and stirred for 5 minutes, followed by the dropwise addition of isopropanol (75 mL) at 40 °C. The reaction mixture was concentrated to 25 mL under reduced pressure and stirred overnight at 0 °C. The suspension was then filtered, and the resulting crystals were washed with isopropanol (5 mL) cooled to 0 °C and dried under reduced pressure at 40 °C to obtain propyl-2-en-1-yl 4,6-O-benzyl-α-D-galactofuranoside (represented by formula G-1) as white crystals (5.35 g, yield 76.3%). 1 H-NMR(500 MHz, METHANOL-D4) δ 7.53 - 7.52 (dd, J = 7.5, 2.0 Hz, 2H), 7.34 (m, 3H), 5.98 (qd, J = 11.1, 5.4 Hz, 1H), 5.59 (s, 1H), 5.35 (d, J = 18.9 Hz, 1H), 5.19 (d, J = 10.3 Hz, 1H), 4.95 (d, J = 4.0 Hz, 1H), 4.26 (d, J = 3.4 Hz, 1H), 4.22 (dd, J = 13.2,5.2 Hz, 1H), 4.13 (s, 2H), 4.08(q, J = 6.5 Hz, 1H), 3.92 (ddd, J = 24.1, 10.3, 3.4 Hz, 2H), 3.74 (s, 1H). 13 C-NMR(125 MHz, METHANOL-D4) δ 64.60, 69.70, 70.03, 70.08, 70.34, 78.07, 100.22, 102.28, 117.58, 127.54, 129.02, 129.86, 135.59, 139.77. MS(ESI)m / z: 309 (M+H) + 307 (MH) - . Example 39 Prop-2-en-1-yl 2,3-di-O-benzoyl-4,6-O-benzyl-α-D-galactofuranoside (compound represented by formula G-2) [Chemical 248] (Step V-1) Benzoyl chloride (47.87 g, 340.54 mmol) was added dropwise to a pyridine (150 mL) solution of prop-2-en-1-yl 4,6-O-benzyl-α-D-galactofuranoside (represented by formula G-1) (30.0 g, 97.30 mmol) at temperatures below 40 °C, and the mixture was stirred at the same temperature for 2 hours. After confirming the completion of the reaction by HPLC, the mixture was cooled to 20 °C-30 °C, ethanol (450 mL) was added, followed by water (300 mL) dropwise over 30 minutes. After stirring the slurry at 20℃-30℃ for 1 hour, the precipitated crystals were filtered. The filtered crystals were washed with a mixture of ethanol and water (75 / 75 mL) and dried under reduced pressure at 40℃ to obtain prop-2-en-1-yl 2,3-di-O-benzoyl-4,6-O-benzyl-α-D-galactofuranoside (the compound represented by formula G-2) as white crystals (47.9 g, yield 95%). 1 H-NMR (500 MHz, CDCl) 3) δ 8.03 - 7.98 (m, 4H), 7.55 - 7.46 (m, 4H), 7.40 - 7.30 (m, 7H), 5.90 - 5.78 (m, 2H), 5.82 (s, 1H), 5.57 (s, 1H), 5.42 (d, J = 1.7 Hz, 1H), 5.31 (dd, J = 17.2, 1.7 Hz, 1H), 5.15 (dd, J = 1.7, 10.5 Hz, 1H), 4.66 (s, 2H), 4.33 (d, J = 12.5 Hz, 1H), 4.26 (dd, J = 12.5, 4.5 Hz, 1H), 4.12 (dd, J = 12.5, 1.0 Hz, 1H), 4.08 (dd, J = 6.5, 13.5 Hz, 1H), 3.95 (s, 1H). 13 C-NMR (125 MHz, CDCl) 3) δ 166.1, 165.8, 137.5, 133.4, 133.2, 133.1, 129.8, 129.7, 129.5, 129.4, 128.8, 128.3, 128.1, 126.1, 117.5, 100.6, 96.2, 74.2, 69.3, 69.1, 68.7, 68.6, 62.4. HRMS(ESI + [M+H] + C 30 H 29 O 8: Calculated value of 517.1857; Experimental value: 517.1880. Example 40 Prop-2-en-1-yl 2,3-di-O-benzoyl-α-D-galactofuranoside (compound represented by formula G-3) [Chem. 249] (Step V-2) A solution of propen-2-en-1-yl 2,3-di-O-benzoyl-4,6-O-benzyl-α-D-galactofuranoside (the compound represented by formula G-2) (47.1 g, 91.18 mmol) in acetonitrile (377 mL) was heated to 45°C. Water (24 mL) and concentrated hydrochloric acid (9.2 g, 91.18 mmol) were added, and the mixture was stirred at the same temperature for 30 minutes. Water (353 mL) was added dropwise over 3 hours at 45°C–50°C, followed by stirring for another 30 minutes. After confirming the reaction was complete by HPLC, sodium acetate (11.22 g, 136.78 mmol), ethyl acetate (942 mL), and water (471 mL) were added. The mixture was cooled to below 25°C, and the layers were separated to obtain the organic layer. The obtained organic layer was washed twice with water (471 mL) and then further washed with 20% saline solution (236 mL). The organic layer was concentrated to 141 mL under reduced pressure, toluene (707 mL) was added, and the solution was concentrated again to 141 mL under reduced pressure. Toluene (236 mL) was added to the obtained concentrate, and the solution was concentrated to 141 mL under reduced pressure. The concentrate was cooled to 0℃~5℃, and a slurry containing neutral silicone (silicone 60N, manufactured by Kanto Chemical, particle size: 40~50 μm, 141 g) containing toluene was added and cooled to 0℃~5℃. The mixture was stirred at the same temperature for 15 minutes to allow the product to be adsorbed onto the silicone, and then filtered. The silica gel solid phase containing the product was washed with toluene (942 mL) at 0–5 °C (the filtrate from the toluene washing was discarded). The target compound was then desorbed from the silica gel using cyclopentyl methyl ether (707 mL) to obtain a cyclopentyl methyl ether solution of prop-2-en-1-yl 2,3-di-O-benzoyl-α-D-galactofuranoside (the compound represented by formula G-3) (quantitative value 36.2 g, quantitative yield 93%). This solution was used in the next step. Example 41 5-Acetamide-3,5-dideoxy-D-glycerol-D-galacto-2-pyranonesulfonate methyl ester monohydrate (compound represented by formula G-5) [Chem. 250] (Step V-3) Add sulfuric acid (1.0 g, 10.20 mmol) to a methanol (321 mL) solution of 5-acetylamine-3,5-dideoxy-D-glycerol-D-galacto-2-pyranonelactone acid (the compound represented by formula G-4) (40.1 g, 129.66 mmol) and methyl orthoformate (15.60 mL, 142.59 mmol), heat to 40°C and stir for 3 hours. After confirming the reaction is complete by HPLC, cool to 25°C, add dimethylacetylamine (40 mL), and concentrate to 160 mL under reduced pressure. Adjust the temperature of the concentrate to 15°C, add water (20 mL) and ethyl acetate (722 mL), stir at 25°C for 1 hour, cool the slurry to 0°C–5°C, and stir at the same temperature for 2 hours. The precipitated crystals were filtered, and the separated crystals were washed with ethyl acetate (80 mL) at 0℃~5℃ and dried under reduced pressure at 40℃ to obtain methyl 5-acetylamine-3,5-dideoxy-D-glycerol-D-galacto-2-pyranone methyl ester monohydrate (represented by formula G-5) as white crystals (41.1 g, yield 93%). 1 H-NMR (500 MHz, CD) 3OD) δ 4.07 - 3.98 (m, 2H), 3.85 - 3.77 (m, 2H), 3.78 (s, 3H), 3.72 - 3.68 (m, 1H), 3.62 (dd, J = 10.9, 5.7 Hz, 1H), 3.48 (dd, J = 9.2, 1.1 Hz, 1H), 2.22 (dd, J = 12.9, 4.9 Hz, 1H), 2.02 (s, 3H), 1.89 (dd, J = 12.6, 11.5 Hz, 1H). 13 C-NMR (125 MHz, CD 3OD) δ 175.2, 175.1, 171.8, 96.6, 72.1, 72.0, 71.6, 70.1, 67.9, 64.8, 54.4, 54.3, 53.2, 40.7, 22.7, 22.7. HRMS(ESI + [M+H] + C 12 H 22 NO Calculated value of 9: 324.1289; Experimental value: 324.1288. Example 42 Methyl 5-acetamide-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycerol-D-galacto-2-pyranoneranone (compound represented by formula G-6) [Chem. 251] (Step V-4) The temperature of an acetonitrile (403 mL) slurry of methyl 5-acetylamine-3,5-dideoxy-D-glycerol-D-galacto-2-pyranonesulfonate monohydrate (the compound represented by formula G-5) (40.3 g, 118.07 mmol) was adjusted to 25°C. Acetic anhydride (60.27 g, 590.36 mmol) and p-toluenesulfonic acid monohydrate (1.12 g, 5.89 mmol) were added, and the mixture was stirred at 25°C for 24 hours. Subsequently, the reaction mixture was cooled to 15°C, and acetic anhydride (12.05 g, 118.03 mmol) was added. The mixture was stirred at the same temperature for 47 hours. After confirming the completion of the reaction by HPLC, methanol (40 mL) was added, the temperature was adjusted to 25°C, and the mixture was stirred at the same temperature for 2 hours. Next, sodium acetate (0.97 g, 11.82 mmol) was added, and the mixture was stirred at the same temperature for 1 hour. The reaction solution was concentrated to 120 mL under reduced pressure, cooled to 0-5°C, and then ethyl acetate (403 mL) and water (161 mL) were added. Triethylamine was added while stirring at 0-5°C to adjust the pH to 7.0. The organic layer obtained by separation was washed twice with 10% saline (121 mL) and concentrated to 200 mL under reduced pressure. Ethyl acetate (605 mL) was added to the concentrate, and the mixture was concentrated again to 200 mL under reduced pressure. Ethyl acetate (40 mL) was added to the concentrate, seed crystals were inoculated, and the mixture was stirred at 25°C for 4 hours. Then, heptane (302 mL) was added dropwise over 30 minutes. After stirring the slurry at 25°C for 2 hours, the precipitated crystals were filtered. The filtered crystals were washed with a mixture of ethyl acetate and heptane (67 / 135 mL) and dried under reduced pressure at 35°C to obtain methyl 5-acetamide-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycerol-D-galacto-2-pyranone methyl ester (represented by formula G-6) as white crystals (44.1 g, yield 76%). 1 H-NMR (500 MHz, CDCl) 3) δ 6.28 (d, J = 10.3 Hz, 1H), 5.41 (dd, J = 4.6, 2.3 Hz, 1H), 5.28 - 5.23 (m, 1H), 5.21 - 5.14 (m, 1H), 5.09 (s, 1H), 4.62 (dd, J = 12.3, 2.6 Hz, 1H), 4.28 (dd, J = 10.3, 2.3 Hz, 1H), 4.21 - 4.11 (m, 1H), 4.04 (dd, J = 12.3, 8.3 Hz, 1H), 3.85 (s, 3H), 2.24 - 2.20 (m, 2H), 2.16 (s, 3H), 2.12 (s, 3H), 2.03 (s, 3H), 2.01 (s, 3H), 1.91 (s, 3H). 13 C-NMR (125 MHz, CDCl) 3) δ 171.5, 171.1, 170.8, 170.3, 170.2, 168.9, 94.9, 72.1, 71.4, 69.1, 68.3, 62.5, 53.2, 49.1, 36.1, 23.0, 21.0, 20.8, 20.7, 20.7. HRMS(ESI + [M+H] + C 20 H 30 NO 13 Calculated value: 492.1712; Experimental value: 492.1712. Example 43: Methyl 5-acetamide-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-O-(2,2,2-trifluoro-N-phenylacetylino)-D-glycerol-β-D-galacto-2-pyranoneranone (the compound represented by formula G-7) [Chemical 252] (Step V-5) The temperature of a slurry of methyl 5-acetylamine-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycerol-D-galacto-2-pyranonerandone ester (represented by formula G-6) (44.0 g, 89.53 mmol) and molecular sieve 4A powder (particle size less than 10 μm) (22 g) in dichloromethane (352 mL) was adjusted to 20°C. After stirring at the same temperature for 30 minutes, 2,2,2-trifluoro-N-phenyliminoacetyl chloride (26.02 g, 125.35 mmol) was added. Then, N-methylimidazole (11.03 g, 134.33 mmol) was added dropwise, and the mixture was stirred at 20°C for 7.5 hours. After confirming the reaction was complete by HPLC, the reaction solution was filtered and washed with dichloromethane (88 mL) to obtain the filtrate. The obtained filtrate was cooled to 0°C, and 440 mL of cold water was added. Triethylamine was added while stirring at 0°C–5°C to adjust the pH to 7.5. After stirring at 0°C–5°C for 30 minutes, the mixture was separated. The obtained organic layer was washed twice with 440 mL of cold water and then washed with cooled 20% saline solution (220 mL). The solution was concentrated to 88 mL under reduced pressure. Ethyl acetate (440 mL) was added to the concentrate, and the solution was concentrated again to 88 mL under reduced pressure. Tertiary butyl methyl ether (308 mL) was added to the concentrate, seed crystals were inoculated, and the solution was stirred at 20°C for 4 hours. Heptane (264 mL) was added dropwise to the obtained slurry solution over 1 hour. After stirring at the same temperature for 2 hours, the precipitated crystals were filtered. The filtered crystals were washed with a mixture of tert-butyl methyl ether and heptane (132 / 88 mL) and dried under reduced pressure at 35°C to obtain methyl 5-acetamide-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-O-(2,2,2-trifluoro-N-phenylacetylimino)-D-glycerol-β-D-galacto-2-pyranone methyl ester (represented by formula G-7) (39.5 g, yield 67%) as white crystals. 1 H-NMR (500 MHz, CDCl) 3) δ 7.30 - 7.24 (m, 2H), 7.09 (t, J = 7.4 Hz, 1H), 6.72 (d, J = 8.0 Hz, 2H), 5.76 (d, J = 9.7 Hz, 1H), 5.48 - 5.45 (m, 1H), 5.30 (td, J = 10.9, 4.8 Hz, 1H), 5.15 - 5.10 (m, 1H), 4.60 (dd, J = 12.6, 2.3 Hz, 1H), 4.30 (q, J = 10.3 Hz, 1H), 4.23 (dd, J = 10.3,2.3 Hz, 1H), 4.11 (dd, J = 12.3 Hz, 7.7 Hz, 1H), 3.81 (s, 3H), 2.79 (dd, J = 13.5, 4.9 Hz, 1H), 2.21 - 2.15 (m, 1H), 2.16 (s, 3H), 2.10 (s, 3H), 2.07 (s, 3H), 1.90 (s, 3H), 1.75 (s, 3H). 13 C-NMR(125 MHz, CDCl 3) δ 171.0, 170.7, 170.4, 170.2, 170.1, 165.3, 142.6, 141.0(q, 2 J C-F =36.0 Hz), 128.8, 124.6, 119.0, 115.1(q, 1 J C-F =284.4 Hz), 99.7, 73.6, 71.9, 68.3, 68.0, 62.4, 53.1, 48.6, 35.6, 23.0, 20.8, 20.8, 20.7, 20.3. HRMS(ESI + )[M+NH 4] + C 28 H 37 F 3N 3O 13 Calculated value: 680.2273; Experimental value: 680.2314. Example 44 4,7,8,9-Tetra-O-acetyl-5-[acetyl(tert-butoxycarbonyl)amino]-3,5-dideoxy-2-O-(2,2,2-trifluoro-N-phenylacetylimino)-D-glycerol-β-D-galacto-2-pyranone methyl ester (compound represented by formula G-8) [Chemical 253] (Step V-6) To a solution of methyl 5-acetylamine-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-O-(2,2,2-trifluoro-N-phenylacetylimino)-D-glycerol-β-D-galacto-2-pyranonesulfonate (39.0 g, 58.86 mmol) in tetrahydrofuran (390 mL), add ditert-butyl dicarbonate (27.05 g, 123.94 mmol) and dimethylaminopyridine (1.80 g, 14.73 mmol), and heat to reflux. After stirring under reflux for 30 minutes, confirm the end of the reaction by HPLC, and concentrate the reaction solution to 117 mL under reduced pressure. Add toluene (195 mL) to the concentrate, and concentrate again to 117 mL under reduced pressure. The concentrate was filtered using a silicone-filled funnel (Silicone 60N, manufactured by Kanto Chemical, particle size: 40–50 μm, 117 g, wet-filled with toluene), and washed with a toluene-ethyl acetate mixture (8 / 2) (975 mL) to obtain the filtrate. The obtained filtrate was concentrated under reduced pressure (until the weight reached 59 g), and cyclopentyl methyl ether (23 mL) was added. The temperature of the solution was adjusted to 20°C, and heptane (156 mL) was added dropwise over 15 minutes, while stirring at the same temperature for 1 hour. After confirming the precipitation of crystals, heptane (312 mL) was added dropwise over 1 hour. The precipitated crystals were filtered, and the separated crystals were washed with heptane (78 mL) and dried under reduced pressure at 35°C to obtain methyl 4,7,8,9-tetra-O-acetylated-5-[acetylated(tert-butoxycarbonyl)amino]-3,5-dideoxy-2-O-(2,2,2-trifluoro-N-phenylacetylinimino)-D-glycerol-β-D-galacto-2-pyranone methyl ester (represented by formula G-8) (37.0 g, yield 82%) as white crystals. 1 H-NMR (500 MHz, CDCl) 3) Note) It was detected as a mixture of ca.1 / 4 isomers. Major isomers: δ 7.27 (t, J = 8.9 Hz, 2H), 7.09 (t, J = 7.2 Hz, 1H), 6.73 (d, J = 8.0 Hz, 2H), 5.75 - 5.65 (m, 1H), 5.31 (d, J = 4.6 Hz, 1H), 5.18 - 5.14 (m, 1H), 5.15 (d, J = 6.0 Hz, 2H), 4.54 (dd, J = 12.0, 2.0 Hz, 1H), 4.08 (dd, J = 12.6, 6.9 Hz, 1H), 3.84 (s, 3H), 2.90 (dd, J = 13.7, 5.2 Hz, 1H), 2.39 (s, 3H), 2.25 (dd, J = 13.7, 11.2 Hz, 1H), 2.09 (s, 3H), 2.07 (s, 3H), 1.99 (s, 3H), 1.77 (s, 3H), 1.62 (s, 9H). Minor isomers: δ 6.76 (d, J = 8.0 Hz, 2H), 5.85 - 5.80 (m, 1H), 5.29 - 5.25 (m, 1H), 5.22 - 5.19 (m, 1H), 4.44 (d, J = 11.0 Hz, 1H), 4.15 - 4.11 (m, 1H), 3.03 (dd, J = 14.0, 5.0 Hz, 1H). 2.41 (s, 3H), 2.12 (s, 3H), 2.00 (s, 3H), 1.88 (s, 3H), 1.74 (s, 3H), 1.54 (s, 9H). 13 C-NMR (125 MHz, CDCl) 3) Mixture: δ 173.7, 170.4, 170.2, 170.0, 169.9, 165.4, 151.7, 142.8, 128.7, 124.5, 119.1, 100.6, 85.2, 72.8, 71.3, 67.7, 65.9, 62.0, 53.1, 52.0, 36.7, 27.9, 27.7, 26.6, 20.8, 20.7, 20.6, 20.3. HRMS(ESI + )[M+NH 4] + C 33 H 45 F 3N 3O 15 Calculated value: 780.2797; Experimental value: 780.2801. Example 45 Prop-2-en-1-yl 2,3-di-O-benzoyl-6-O-{4,7,8,9-tetra-O-acetylgluco-5-[acetylgluco-(tert-butoxycarbonyl)amino]-3,5-dideoxy-1-methyl-D-glycerol-α-D-galacto-2-pyranonesulosyl}-α-D-galactofuranose (compound represented by formula G-9) [Chemical 254] (Step V-7) A cyclopentyl methyl ether solution of prop-2-en-1-yl 2,3-di-O-benzoyl-α-D-galactofuranyl glycoside (represented by formula G-3) (quantitative value 31.46 g, 73.43 mmol) was concentrated to 105 mL under reduced pressure and then added to a cyclopentyl methyl ether solution (175 mL) of methyl 4,7,8,9-tetra-O-acetylated-5-[acetylated(tert-butoxycarbonyl)amino]-3,5-dideoxy-2-O-(2,2,2-trifluoro-N-phenylacetylinimino)-D-glycerol-β-D-galacto-2-pyranone methyl ester (represented by formula G-8) (35.0 g, 45.89 mmol). Next, cyclopentyl methyl ether was added to the obtained mixed solution to adjust the total volume to 350 mL (a mixed solution of cyclopentyl methyl ether of the compounds represented by formula G-3 and formula G-8). In another container, cyclopentyl methyl ether (525 mL) and molecular sieve 4A powder (particle size less than 10 μm) (17.5 g) were added. After cooling to -60°C, trimethylsilane trifluoromethanesulfonate (4.2 mL, 23.24 mmol) was added. For this solution, the mixed solution of cyclopentyl methyl ether of the compounds represented by formula G-3 and formula G-8 was added dropwise over 4.5 hours with thorough stirring at -60°C, and stirred at the same temperature for 2 hours. After confirming the completion of the reaction by HPLC, triethylamine (4.5 mL, 32.12 mmol) was added, and the reaction solution was heated to 0°C. Subsequently, diatomaceous earth 545 (35.00 g) was added, and the reaction solution was filtered and washed with cyclopentyl methyl ether (175 mL). Water (350 mL) was added to the filtrate, and the mixture was separated. Then, 0.5 N hydrochloric acid water (350 mL) was added to the organic layer, and the mixture was stirred at 20°C for 2 hours. After confirming the decomposition of byproducts by HPLC, the organic layer was obtained by separation. The organic layer was washed with water (350 mL) and 20% saline (175 mL), and concentrated to 70 mL under reduced pressure. Toluene (700 mL) was added to the concentrate, and the mixture was concentrated to 70 mL under reduced pressure. Toluene (700 mL) and neutral silicone (silicone 60N, manufactured by Kanto Chemical, particle size: 40–50 μm, 158 g) were added to the concentrate again, and the mixture was stirred at 20°C for 30 minutes. After the product is adsorbed onto the silicone, it is filtered. The silicone solid phase containing the product is washed with toluene (1575 mL) (the filtrate from the toluene washing is discarded). The target analyte is then desorbed from the silicone using ethyl acetate (875 mL).The obtained ethyl acetate solution was concentrated to 70 mL under reduced pressure, and toluene (175 mL) was added. The solution was then concentrated again to 70 mL under reduced pressure to obtain a toluene solution of prop-2-en-1-yl 2,3-di-O-benzoyl-6-O-{4,7,8,9-tetra-O-acetylgluco-5-[acetylgluco-(tert-butoxycarbonyl)amino]-3,5-dideoxy-1-methyl-D-glycerol-α-D-galacto-2-pyranoneliosyl}-α-D-galactofuranoside (the compound represented by formula G-9). This solution was used in the next step. Example 46 Prop-2-en-1-yl 6-O-{5-acetaminophen-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-methyl-D-glycerol-α-D-galacto-2-pyranonesyl}-2,3-di-O-benzoyl-α-D-galactofuranoside (compound represented by formula G-10) [Chemical 255] (Step V-8) To a toluene solution of prop-2-en-1-yl 2,3-di-O-benzoyl-6-O-{4,7,8,9-tetra-O-acetylgluco-5-[acetylgluco-(tert-butoxycarbonyl)amino]-3,5-dideoxy-1-methyl-D-glycerol-α-D-galacto-2-pyranonelitoyl}-α-D-galactofuranylglycoside (the compound represented by formula G-9), dichloromethane (525 mL) and copper(II) trifluoromethanesulfonate (8.30 g, 22.95 mmol) were added, and the mixture was heated to 40°C and stirred at the same temperature for 2 hours. After confirming the completion of the reaction by HPLC, the mixture was cooled to 25°C and concentrated to 70 mL under reduced pressure. Ethyl acetate (525 mL) was added to the concentrate, and the mixture was washed three times with 5% saline solution (350 mL). Heptane (263 mL) was then added to the organic layer, and the mixture was washed four times with 20% methanol-water solution (525 mL). After HPLC confirmation that the β-excimer of compound 8, a byproduct of the glycosylation reaction, had been removed by the aqueous layer, the organic layer was concentrated to 70 mL under reduced pressure. Add 525 mL of isopropyl acetate to the concentrate and concentrate to 350 mL under reduced pressure to obtain an isopropyl acetate solution of propyl-2-en-1-yl 6-O-{5-acetaminophen-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-methyl-D-glycerol-α-D-galacto-2-pyranonelitoyl}-2,3-di-O-benzoyl-α-D-galactofuranoside (the compound represented by formula G-10). Use this solution for the next step. Example 47 Prop-2-en-1-yl 4-O-acetyl-2,3-di-O-benzoyl-6-O-[4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-(diacetylamino)-1-methyl-D-glycerol-α-D-galacto-2-nonylpyranose]-α-D-galactofuranose (compound represented by formula G-11) [Chemical 256] (Step V-9) To a solution of isopropyl acetate of propen-1-yl 6-O-{5-acetylamine-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-methyl-D-glycerol-α-D-galacto-2-pyranone-sacchariyl}-2,3-di-O-benzoyl-α-D-galactofuranylglycoside (the compound represented by formula G-10), add p-toluenesulfonic acid monohydrate (0.88 g, 4.62 mmol), heat to reflux temperature (internal temperature around 90°C), and stir at the same temperature for 3 hours. After confirming the reaction is complete by HPLC, cool to 25°C, add triethylamine (0.95 mL, 6.85 mmol), and concentrate to 70 mL under reduced pressure. Add toluene (350 mL) to the concentrate, and concentrate again to 70 mL under reduced pressure. Add toluene (630 mL) to the concentrate, then add neutral silicone (silicone 60N, manufactured by Kanto Chemical, particle size: 40-50 μm, 123 g), and stir at the same temperature for 30 minutes to allow the product to be adsorbed onto the silicone before filtration. The silica gel solid phase containing the product was washed with toluene (1925 mL) and a toluene / ethyl acetate mixture (97 / 3, 1400 mL) (the filtrate from the washing was discarded). The target compound was then desorbed from the silica gel solid phase containing the product using ethyl acetate (1050 mL). The resulting ethyl acetate solution was concentrated under reduced pressure to obtain a white foamy solid, prop-2-en-1-yl-4-O-acetylglyl-2,3-di-O-benzoyl-6-O-[4,7,8,9-tetra-O-acetylglyl-3,5-dideoxy-5-(diacetylglylamino)-1-methyl-D-glycerol-α-D-galacto-2-pyranone-yl]-α-D-galactofuranylglycoside (the compound represented by formula G-11) (30.1). g, yield 67% (based on compound G-8) (containing 0.42 equivalents of toluene (approximately 4% by weight)). 1 H-NMR (500 MHz, CDCl) 3) δ 7.99 (d, J = 8.4 Hz, 2H), 7.88 (dd, J = 8.4, 1.4 Hz, 2H), 7.53 - 7.47 (m, 2H), 7.37 (dt, J = 14.7, 6.9 Hz, 4H), 5.90 - 5.82 (m, 1H), 5.82 (dd, J = 10.9, 3.4 Hz, 1H), 5.73 (d, J = 2.9 Hz, 1H), 5.58 (dd, J = 10.9, 4.0 Hz, 1H), 5.51 (td, J = 10.6, 5.0 Hz, 1H), 5.35 - 5.30 (m, 3H), 5.17 - 5.15 (m, 2H), 4.94 (dd, J = 10.3, 1.7 Hz, 1H), 4.38 - 4.27 (m, 3H), 4.20 - 4.13 (m, 2H), 4.08 (dd, J = 13.2, 5.7 Hz, 1H), 3.94 (dd, J = 10.3, 6.3 Hz, 1H), 3.82 (s, 3H), 3.50 (dd, J = 9.7, 7.4 Hz, 1H), 2.73 (dd, J = 13.2, 5.2 Hz, 1H), 2.37 (s, 3H), 2.31 (s, 3H), 2.19 (s, 3H), 2.15 (s, 3H), 2.14 (s, 3H), 2.03 (s, 3H), 1.97 (s, 3H), 1.86 (dd, J = 13.2, 10.9 Hz, 1H). 13 C-NMR(125 MHz, CDCl 3) δ 174.5, 173.6, 170.5, 170.1, 169.9, 169.8, 169.6, 167.3, 166.0, 165.5, 133.5, 133.3, 133.1, 129.8, 129.5, 129.4, 128.4, 128.3, 117.5, 98.6, 95.5, 77.2, 69.8, 68.9, 68.6, 68.6, 68.3, 68.3, 67.5, 67.0, 66.7, 62.4, 61.8, 57.0, 52.9, 38.7, 27.9, 25.9, 21.0, 20.9, 20.7, 20.7, 20.6. HRMS(ESI + [M+H] + C 47 H 56 NO 22 Calculated value: 986.3288; Experimental value: 986.3277. Regarding the obtained compound, the spectrum was confirmed to be consistent with the following literature: J. Org. Chem. 2016, 81, 10600-10616. Example 48 4-O-acetyl-2,3-di-O-benzoyl-6-O-[4,7,8,9-tetra-O-acetyl-3,5-dideoxy-5-(diacetylamino)-1-methyl-D-glycerol-α-D-galacto-2-nonylpyranose]-D-galactofuranose (compound represented by formula G-12) [Chemical 257] (Step V-10) A methanol solution (290 mL) of propen-2-en-1-yl4-O-acetylglyl-2,3-di-O-benzoyl-6-O-[4,7,8,9-tetra-O-acetylglyl-3,5-dideoxy-5-(diacetylglylamino)-1-methyl-D-glycerol-α-D-galacto-2-pyranone-yl]-α-D-galactofuranylglycoside (the compound represented by formula G-11) (29.00 g, 29.41 mmol), 1,3-dimethylbarbituric acid (9.19 g, 58.86 mmol), and triphenylphosphine (2.31 g, 8.81 mmol) was repeatedly purged with nitrogen five times under reduced pressure for degassing. Then, palladium(II) acetat...

Claims

1. A method for manufacturing an oligosaccharide, the oligosaccharide being represented by the following formula A-13, the method comprising: (Step I-1) The step of generating the compound represented by formula A-7, which includes the step of generating the compound represented by formula A-5 by forming an α-1,6-glycosidic bond between the compound represented by formula A-3 and the compound represented by formula A-4; (Step I-2) The step of generating the compound represented by formula A-10, which includes the step of generating the compound represented by formula A-9 by forming a β-1,4-glycosidic bond between the compound represented by formula A-7 and the compound represented by formula A-8; (Step I-3) The step of generating the oligosaccharide represented by formula A-13, which includes the step of generating the compound represented by formula A-12 by forming a β-1,2-glycosidic bond between the compound represented by formula A-10 and the compound represented by formula A-11.

2. The method of claim 1, wherein step I-2 above includes: The compound represented by formula A-9 above is generated by reacting the compound with a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid.

3. The method of claim 2, wherein the alkyl ester of the perfluorocarboxylic acid is methyl trifluoroacetate, ethyl trifluoroacetate, propyl trifluoroacetate, isopropyl trifluoroacetate, butyl trifluoroacetate, methyl pentafluoropropionate, ethyl pentafluoropropionate, propyl pentafluoropropionate, isopropyl pentafluoropropionate, methyl heptafluorobutyrate, ethyl heptafluorobutyrate, propyl heptafluorobutyrate, isopropyl heptafluorobutyrate, butyl heptafluorobutyrate, methyl nonafluoropentanoate, ethyl nonafluoropentanoate, propyl nonafluoropentanoate, isopropyl nonafluoropentanoate, butyl nonafluoropentanoate, methyl undecanohexanoate, ethyl undecanohexanoate, propyl undecanohexanoate, isopropyl undecanohexanoate, or butyl undecanohexanoate.

4. The method of claim 2, wherein the strong base is selected from the group consisting of sodium, lithium, and potassium salts of metal amides; sodium, lithium, potassium, cesium, and barium salts of C1-C20 alkoxides; sodium hydride, potassium hydride, lithium hydride, butyllithium, potassium carbonate, sodium carbonate, cesium carbonate, lithium carbonate, potassium phosphate, sodium phosphate, cesium phosphate, lithium phosphate, diazabicycloundecene (DBU), diazabicyclononene (DBN), and 1,1,3,3-tetramethylguanidine (TMG); and combinations thereof.

5. The method of claim 2, wherein the strong base is potassium terbutoxide, sodium terbutoxide, lithium terbutoxide, or LHMDS (lithium bis(trimethylsilane)amino).

6. The method of claim 1, wherein steps I-3 above include: By reacting the compound represented by formula A-12 with DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone) in a mixed solvent of fluorinated alcohol and water, the 2-naphthylmethyl group in the compound represented by formula A-12 is deactivated, thereby generating the oligosaccharide shown in formula A-13.

7. The method of claim 1, wherein the compound represented by formula A-11 above is manufactured by steps including steps Y-1 and Y-2: (Step Y-1) the step of generating the compound represented by formula B-4 below, which includes generating the compound represented by formula B-3 below by forming a β-1,4-glycosidic bond between the compound represented by formula B-1 below and the compound represented by formula B-2 below; (Step Y-2) the step of generating the compound represented by formula B-5 below by adding lithium third butoxide or lithium third pentanol to a solvent containing the compound represented by formula B-4 above and benzyl halide or benzyl sulfonate, thereby protecting the hydroxyl groups present in the compound represented by formula B-4 above with benzyl groups.

8. The method of claim 7 further includes the step of purifying the compound represented by formula B-5 by: opening the phthalimide group in the compound represented by formula B-5, and then reacting it with cinconidine to generate a crystalline compound represented by formula B-6; separating the crystalline compound represented by formula B-6 from the non-crystalline substance, and adding an acidic aqueous solution and a solvent to remove cinconidine from the compound represented by formula B-6 to generate a compound represented by formula B-7; and then closing the ring-opened phthalimide group in the compound represented by formula B-7 to purify the compound represented by formula B-5.

9. The method of claim 1, further comprising the step of purifying the compound represented by formula A-13 by: opening the phthalimide group in the compound represented by formula A-13, and then forming a salt with (R)-(+)-1-(1-naphthyl)ethylamine, thereby generating a crystalline compound represented by formula A-14; after separating the crystalline compound represented by formula A-14 from the non-crystalline substance, adding an acidic aqueous solution and a solvent to remove the (R)-(+)-1-(1-naphthyl)ethylamine in the compound represented by formula A-14, thereby generating a compound represented by formula A-15; and then closing the ring-opened phthalimide group in the compound represented by formula A-15 to purify the compound represented by formula A-13.

10. A method for manufacturing an oligosaccharide, the oligosaccharide being represented by the following formula D-13, the method comprising the following steps: (Step II-1) a step of generating a compound represented by the following formula D-2, comprising: by means of The process involves: (Step II-2) generating a compound represented by formula D-1 by forming an α-1,3-glycosidic bond between the oligosaccharide represented by formula A-13 and the compound represented by formula A-3; (Step II-3) generating a compound represented by formula D-5, wherein the step of generating a compound represented by formula D-5 includes forming a β-1,2-glycosidic bond between the compound represented by formula D-2 and the compound represented by formula D-3 to generate a compound represented by formula D-4; and (Step II-4) generating a compound represented by formula D-5 by forming a protecting group selected from aryloxycarbonyl (COOAr), acetyl (Ac), 2,2,2-trichloroethoxycarbonyl (Troc), and phthalimide (Pht) on the compound represented by formula D-5. The amine group in the compound represented is protected to generate the compound represented by the following formula D-6 (where R5 is an aryloxycarbonyl (COOAr), acetyl (Ac), or 2,2,2-trichloroethoxycarbonyl (Troc), and R6 is a hydrogen atom, or R5 and R6 together with the nitrogen atoms they are bonded to form a phthalimide group), or by removing the acetyl (Ac) group from the compound represented by the following formula D-4, the compound represented by the following formula D-6 is generated (where R5 and R6 together with the nitrogen atoms they are bonded to form a phthalimide group); (Step II-3) The step of generating the compound represented by formula D-11 (where M+ is a sodium ion, lithium ion, potassium ion, or a protonated triethylamine cation) includes forming a β-1,4-glycosidic bond between the compound represented by formula D-6 and the compound represented by formula D-7 to generate the compound represented by formula D-8. The compound represented by formula D-8 (where R5 is an aryloxycarbonyl (COOAr), acetyl (Ac), or 2,2,2-trichloroethoxycarbonyl (Troc), and R6 is a hydrogen atom, or R5 and R6 together with the nitrogen atom they are bonded to form a phthalimide group) is then subjected to the removal of the protecting groups of the amine and alcohol groups on the compound represented by formula D-8, thereby generating the compound represented by formula D-9 (where M+ is a sodium ion, lithium ion, potassium ion, or a protonated triethylamine cation); (Step II-4) The oligosaccharide represented by formula D-13 is generated by reacting the compound represented by formula D-11 with the compound represented by formula D-12.

11. The method of claim 10, wherein step II-1 above includes: The compound represented by formula D-1 is reacted with a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid to produce the compound represented by formula D-2.

12. The method of claim 11, wherein the alkyl ester of the perfluorocarboxylic acid is methyl trifluoroacetate, ethyl trifluoroacetate, propyl trifluoroacetate, isopropyl trifluoroacetate, butyl trifluoroacetate, methyl pentafluoropropionate, ethyl pentafluoropropionate, propyl pentafluoropropionate, isopropyl pentafluoropropionate, methyl heptafluorobutyrate, ethyl heptafluorobutyrate, propyl heptafluorobutyrate, isopropyl heptafluorobutyrate, butyl heptafluorobutyrate, methyl nonafluoropentanoate, ethyl nonafluoropentanoate, propyl nonafluoropentanoate, isopropyl nonafluoropentanoate, butyl nonafluoropentanoate, methyl undecanohexanoate, ethyl undecanohexanoate, propyl undecanohexanoate, isopropyl undecanohexanoate, or butyl undecanohexanoate.

13. The method of claim 11, wherein the strong base is selected from the group consisting of sodium, lithium, and potassium salts of metal amides; sodium, lithium, potassium, cesium, and barium salts of C1-C20 alkoxides; sodium hydride, potassium hydride, lithium hydride, butyllithium, potassium carbonate, sodium carbonate, cesium carbonate, lithium carbonate, potassium phosphate, sodium phosphate, cesium phosphate, lithium phosphate, diazabicycloundecene (DBU), diazabicyclononene (DBN), and 1,1,3,3-tetramethylguanidine (TMG); and combinations thereof.

14. The method of claim 11, wherein the strong base is potassium terbutoxide, sodium terbutoxide, lithium terbutoxide, or LHMDS (lithium bis(trimethylsilane)amino).

15. The method of claim 10, wherein step II-3 above includes: The compound represented by formula D-6 is generated by protecting the amine group in the compound represented by formula D-5 with an aryloxycarbonyl group (COOAr).

16. The method of claim 10, wherein the compound represented by formula D-12 above is obtained by a purification method comprising the steps of: adding the following compound represented by formula E-1 (where R7 is a hydrogen atom, methyl, or methoxy) to a solution containing crude compound represented by formula D-12 above, to generate the following crystalline compound represented by formula E-2 (where R7 is a hydrogen atom, methyl, or methoxy); and isolating the crystalline compound and then extracting the compound represented by formula D-12 above from the isolated crystalline compound.

17. The method of claim 10 further includes the following steps: generating a crystalline compound represented by the following formula D-5-FMA by forming a salt with fumaric acid, and then separating and purifying the crystalline compound represented by the above formula D-5-FMA from the non-crystalline substance.

18. A method for producing a compound represented by formula A-10, comprising the step of reacting a compound represented by formula A-9 with a strong base in the presence of an alkyl ester of a perfluorocarboxylic acid.

19. The method of claim 18, wherein the alkyl ester of the perfluorocarboxylic acid is methyl trifluoroacetate, ethyl trifluoroacetate, propyl trifluoroacetate, isopropyl trifluoroacetate, butyl trifluoroacetate, methyl pentafluoropropionate, ethyl pentafluoropropionate, propyl pentafluoropropionate, isopropyl pentafluoropropionate, methyl heptafluorobutyrate, ethyl heptafluorobutyrate, propyl heptafluorobutyrate, isopropyl heptafluorobutyrate, butyl heptafluorobutyrate, methyl nonafluoropentanoate, ethyl nonafluoropentanoate, propyl nonafluoropentanoate, isopropyl nonafluoropentanoate, butyl nonafluoropentanoate, methyl undecanohexanoate, ethyl undecanohexanoate, propyl undecanohexanoate, isopropyl undecanohexanoate, or butyl undecanohexanoate.

20. The method of claim 18, wherein the strong base is selected from sodium, lithium, and potassium salts of metal amides; sodium, lithium, potassium, cesium, and barium salts of C1-C20 alkoxides; sodium hydride, potassium hydride, lithium hydride, butyllithium, potassium carbonate, sodium carbonate, cesium carbonate, lithium carbonate, potassium phosphate, sodium phosphate, cesium phosphate, lithium phosphate, diazabicycloundecene (DBU), diazabicyclononene (DBN), and 1,1,3,3-tetramethylguanidine (TMG); and combinations thereof.

21. The method of claim 18, wherein the strong base is potassium terbutoxide, sodium terbutoxide, lithium terbutoxide, or LHMDS (lithium bis(trimethylsilane)amino).

22. A method for manufacturing an oligosaccharide of formula A-13, comprising the steps of reacting a compound represented by formula A-12 with DDQ (2,3-dichloro-5,6-dicyano-p-benzoquinone) in a mixed solvent of fluoroalcohol and water, thereby de-dissociating the 2-naphthylmethyl group in the compound represented by formula A-12.

23. A method for generating a compound represented by formula D-8 (where R5 is an aryloxycarbonyl (COOAr), acetyl (Ac), or 2,2,2-trichloroethoxycarbonyl (Troc), and R6 is a hydrogen atom, or R5 and R6 together with the nitrogen atoms to which they are bonded form a phthalimide group), comprising the steps of: generating a compound represented by formula D-6 (where R5 is an aryloxycarbonyl (COOAr), acetyl (Ac), or 2,2,2-trichloroethoxycarbonyl (Troc), and R6 is a hydrogen atom, or R5 and R6 together with the nitrogen atoms to which they are bonded form a phthalimide group), and then subjecting the compound represented by formula D-6 to a β-1,4-glycosidic bond with a compound represented by formula D-7, thereby generating the compound represented by formula D-8.

24. The method of claim 23, wherein R5 is an aryloxycarbonyl group (COOAr).

25. The method of claim 23, comprising: By removing the protecting groups of the amine group and the acetylated protecting groups of the alcohol in the compound represented by formula D-8 above, the compound represented by formula D-9 is generated (where M+ is a sodium ion, lithium ion, potassium ion, or a protonated triethylamine cation).

26. An oligosaccharide represented by the following formula A-13 or D-13: .

27. A compound selected from the group consisting of compounds represented by the formulas A-5, A-6, A-7, A-9, A-10, A-11, A-12, A-14, A-15, D-1, D-2, D-4, D-5, D-5-FMA, D-6, D-8, D-9, D-10 and D-11: (In the compounds represented by formulas D-6 and D-7, R5 is an aryloxycarbonyl (COOAr), acetyl (Ac), or 2,2,2-trichloroethoxycarbonyl (Troc), and R6 is a hydrogen atom, or R5 and R6 together with the nitrogen atom to which they are bonded form a phthalimide group; in the compounds represented by formulas D-9, D-10 and D-11, M+ is a sodium ion, a lithium ion, a potassium ion, or a protonated triethylamine cation).

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