Bacterial capsular oligosaccharide derivatives, their production method, pharmaceutical compositions, and uses

Abstract

The present application discloses bacterial capsular oligosaccharide derivatives and their preparation, pharmaceutical compositions and uses. The derivatives are represented by formula (I) and the details of the substituents are described in the specification. The derivatives have anti-inflammatory activity and are useful for the treatment of sepsis. TIFF2024537829000083.tif48169

Description

Related Applications

[0001] This application claims priority to a Chinese patent application for invention entitled "Bacterial Capsular Oligosaccharide Derivatives and Their Preparation Methods, Pharmaceutical Compositions, and Uses" filed on September 29, 2021, with application number 202111152832.1, the entire contents of which are incorporated herein by reference. [Technical Field]

[0002] The present specification relates to biopharmaceutical technology, in particular to bacterial capsular oligosaccharide derivatives, and their production methods, pharmaceutical compositions and uses. [Background technology]

[0003] Colwellia psychrerythraea 34H is a psychrophilic bacterium isolated from Arctic ocean sediments. Its capsular polysaccharide mimics antifreeze proteins and has good antifreeze activity, enabling it to adapt to low-temperature environments. In 2015, the capsular polysaccharide structure of Colwellia psychrerythraea 34H bacteria was reported. It is a glycosaminoglycan with amino acid modifications, and its main chain consists of a tetrasaccharide repeating unit of →4)-β-D-GlcA-(1→3)-β-D-GlcNAc-(1→2)-α-D-GalA-(1→3)-β-D-GalNAc-(1→), with one L-threonine attached to the carboxyl group of the galacturonic acid via an amide bond (Sara Carillo, et al., A Unique Capsular Polysaccharide Structure from the Psychrophilic Marine Bacterium Colwellia psychrerythraea 34H That Mimics Antifreeze (Glyco)proteins. J. Am. Chem. Soc. 2015, 137, 179). The disaccharide at the non-reducing end of this tetrasaccharide is a hyaluronic acid disaccharide, and the disaccharide at the reducing end has a novel structure that has not been reported before. However, no other activities of this glycan have been reported other than its antifreeze activity. [ka]

[0004] In 2019, the research team that discovered this glycan structure reported the synthesis of its tetrasaccharide threonine unit. The reported synthesis strategy involved assembling oligosaccharides from four monosaccharide blocks through protecting group manipulation and glycosylation, resulting in the synthesis of the oligosaccharide fragments of the capsular polysaccharide. The synthesis involved over 40 reaction steps from the monosaccharide blocks, with an overall yield of less than 0.028% (Giulia Vessella et al., Synthesis of the tetrasaccharide repeating unit of the cryoprotectant capsular polysaccharide from Colwellia psychrerythraea 34H. Org. Biomol. Chem., 2019, 17, 3129). Therefore, the development of a novel chemical synthesis method for the oligosaccharide fragments of the capsular polysaccharide is of great significance for facilitating medicinal chemistry research. Summary of the Invention

[0005] The following is a summary of the subject matter described herein, which does not limit the scope of protection of the claims.

[0006] In one aspect, the present application provides the use of a bacterial capsular oligosaccharide derivative of formula I or a pharmaceutically acceptable salt, solvate or prodrug thereof as an anti-inflammatory agent, [ka] In formula (I), R1 is OH, an unsubstituted or substituted C1-C6 alkoxy group, an unsubstituted or substituted C2-C6 alkenoxy group, an unsubstituted or substituted C2-C6 alkynyloxy group, an unsubstituted or substituted C1-C6 alkylthio group, an unsubstituted or substituted C1-C6 alkanoyloxy group, or an unsubstituted or substituted areneoxy group; R2 is OH, -N(H)-R 15 , N(R 16 )-R 17 , an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group, wherein R 15 is an amino acid residue that does not contain proline, and R 16 and R 17 together form a proline residue, R3 and R4 are each independently an unsubstituted or substituted C1-C6 alkanoyl group; R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 13 are each independently hydrogen, an unsubstituted or substituted C1-C6 alkanoyl group, or an unsubstituted or substituted C1-C6 alkyl group; R 14 is OH, an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group.

[0007] In a second aspect, the present application provides a method of preventing or treating inflammation, the method comprising administering to an individual in need thereof a therapeutically effective amount of a bacterial capsular oligosaccharide derivative or a pharmaceutically acceptable salt, solvate or prodrug thereof, wherein the derivative has formula I: [ka] In formula (I), R1 is OH, an unsubstituted or substituted C1-C6 alkoxy group, an unsubstituted or substituted C2-C6 alkenoxy group, an unsubstituted or substituted C2-C6 alkynyloxy group, an unsubstituted or substituted C1-C6 alkylthio group, an unsubstituted or substituted C1-C6 alkanoyloxy group, or an unsubstituted or substituted areneoxy group; R2 is OH, -N(H)-R 15 , N(R 16 )-R 17 , an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group, wherein R 15 is an amino acid residue that does not contain proline, and R 16 and R 17 together form a proline residue, R3 and R4 are each independently an unsubstituted or substituted C1-C6 alkanoyl group; R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 13 are each independently hydrogen, an unsubstituted or substituted C1-C6 alkanoyl group, or an unsubstituted or substituted C1-C6 alkyl group; R 14 is OH, an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group.

[0008] In a third aspect, the present application provides a method for producing the bacterial capsular oligosaccharide derivatives, the method comprising: a step of reacting a compound of formula (I-13) with a compound of formula (I-18) to obtain a compound (I-19), [ka] In the compounds of formula (I-13), formula (I-18), or formula (I-19), Ac is an acetyl group, Ph is a phenyl group, Bn is a benzyl group, Me is a methyl group, TFA is a trifluoroacetyl group, and Lev is an acetylpropionyl group.

[0009] In a fourth aspect, the present application provides a novel bacterial capsular oligosaccharide derivative represented by formula (I') or a pharmaceutically acceptable salt, solvate or prodrug thereof: [ka] In formula (I'), R1' is OH, an unsubstituted or substituted C1-C6 alkoxy group, an unsubstituted or substituted C2-C6 alkenoxy group, an unsubstituted or substituted C2-C6 alkynyloxy group, an unsubstituted or substituted C1-C6 alkylthio group, an unsubstituted or substituted C1-C6 alkanoyloxy group, or an unsubstituted or substituted areneoxy group; R2' is OH, -N(H)-R 15 , N(R 16 )-R 17 , an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group, wherein R 15 is an amino acid residue that does not contain proline, and R 16 and R 17 together form a proline residue, R3' and R4' are each independently an unsubstituted or substituted C1-C6 alkanoyl group; R5', R6', R7', R8', R9', R 10 ', R 11 ', R 12 ' and R 13 each ' is independently hydrogen, an unsubstituted or substituted C1-C6 alkanoyl group, or an unsubstituted or substituted C1-C6 alkyl group; R 14' is OH, an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group; In formula (I'), R1' is not an n-propoxy group or an allyloxy group.

[0010] In a fifth aspect, the present application provides a pharmaceutical composition comprising the novel bacterial capsular oligosaccharide derivatives described above.

[0011] In a sixth aspect, the present application provides the use of the above novel bacterial capsular oligosaccharide derivatives or pharmaceutical compositions thereof for anti-inflammatory activity.

[0012] In a seventh aspect, the present application provides the above novel bacterial capsular oligosaccharide derivatives or pharmaceutical compositions thereof for anti-inflammatory activity.

[0013] In an eighth aspect, the present application provides a method of administering the above-mentioned novel bacterial capsular oligosaccharide derivatives or pharmaceutical compositions thereof to an individual to prevent or treat inflammation. [Brief explanation of the drawings]

[0014] The drawings are intended to provide an understanding of the technical solution of the present application, are a part of the specification, and are used to interpret the technical solution of the present application together with the embodiments of the present application, but are not intended to limit the technical solution of the present application. [Figure 1] Figure 1 shows the effect of the present compound CP-1 / CP-2 on NO production in LPS-induced RAW264.7 cells, where NC represents the blank control group, compared with the LPS group, ****p<0.0001, n=3. [Figure 2] Figure 1 shows the effect of the present compound CP-1 / CP-2 on PGE2 production in LPS-induced RAW264.7 cells, where NC represents the blank control group, compared with the LPS group, ****p<0.0001, n=3. [Figure 3]Figure 1 shows the effects of the compounds CP-1 / CP-2 of the present invention on the release of IL-1β, IL-6, and TNF-α in LPS-induced RAW264.7 cells, where NC represents the blank control group, compared with the LPS group, ****p<0.0001, n=3. [Figure 4] Figure 1 shows the effect of the compounds CP-1 / CP-2 of the present invention on the expression of iNOS and COX-2 proteins in LPS-induced RAW264.7 cells. NC represents the blank control group, compared with the LPS group, *p<0.05, **p<0.001, n=3. [Figure 5] 1 shows the effect of the compound of the present invention, CP-1, on the survival rate in an LPS-induced mouse sepsis model. [Figure 6] 1 shows the inhibitory effect of the compound of the present invention, CP-1, on inflammatory factors in the serum of an LPS-induced mouse sepsis model. [Figure 7] 1 shows the inhibitory effect of the compound of the present invention, CP-Me, on inflammatory factors in the serum of an LPS-induced mouse sepsis model. [Figure 8] Male C57BL / 6 mice were divided into control group (a / e), LPS group (b / f), CP-1 group (c / g), and dexamethasone group (d / h). LPS was administered intraperitoneally for 24 hours, and then the histopathology of the mouse lungs was studied by HE staining (A). Inflammation was scored independently by three experimenters (B, n=6). DETAILED DESCRIPTION OF THE INVENTION

[0015] In an embodiment of the first or second aspect, the present application provides a bacterial capsular oligosaccharide derivative of formula I, or a pharmaceutically acceptable salt, solvate or prodrug thereof, for use as an anti-inflammatory agent or in a method for preventing or treating inflammation, [ka] In formula (I), R1 is OH, an unsubstituted or substituted C1-C6 alkoxy group, an unsubstituted or substituted C2-C6 alkenoxy group, an unsubstituted or substituted C2-C6 alkynyloxy group, an unsubstituted or substituted C1-C6 alkylthio group, an unsubstituted or substituted C1-C6 alkanoyloxy group, or an unsubstituted or substituted areneoxy group, and An alkynyloxy group, a substituted C1-C6 alkylthio group, a substituted C1-C6 alkanoyloxy group, and a substituted areneoxy group mean that one or more hydrogen atoms in a C1-C6 alkoxy group, a C2-C6 alkenoxy group, a C2-C6 alkynyloxy group, a C1-C6 alkylthio group, a C1-C6 alkanoyloxy group, or an areneoxy group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkoxy group, a halogen atom, a nitro group, a cyano group, an acetyl group, a propionyl group, and a phenyl group, R2 is OH, -N(H)-R 15 , N(R 16 )-R 17 , an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group, wherein R 15 is an amino acid residue that does not contain proline, and R 16 and R 17 together form a proline residue, and the substituted C1-C6 alkoxy group and substituted areneoxy group mean that one or more hydrogen atoms in the C1-C6 alkoxy group or areneoxy group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkoxy group, a halogen atom, a nitro group, a cyano group, and a phenyl group; R3 and R4 each independently represent an unsubstituted or substituted C1-C6 alkanoyl group, wherein the substituted C1-C6 alkanoyl group means that one or more hydrogen atoms in the C1-C6 alkanoyl group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkanoyl group, a halogen atom, a nitro group, a cyano group, an acetyl group, a propionyl group, and a phenyl group; R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 13 are each independently hydrogen, an unsubstituted or substituted C1-C6 alkanoyl group, or an unsubstituted or substituted C1-C6 alkyl group, wherein the substituted C1-C6 alkanoyl group or substituted C1-C6 alkyl group means that one or more hydrogen atoms in the C1-C6 alkanoyl group or C1-C6 alkyl group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkoxy group, a halogen atom, a nitro group, a cyano group, an acetyl group, a propionyl group, and a phenyl group, and optionally the phenyl group may be substituted with one or more groups selected from the group consisting of a C1-C4 alkoxy group and a nitro group; R 14 is OH, an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group, and the substituted C1-C6 alkoxy group and substituted areneoxy group mean that one or more hydrogen atoms in the C1-C6 alkoxy group or areneoxy group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkoxy group, a halogen atom, a nitro group, a cyano group, and a phenyl group.

[0016] In some embodiments of the first or second aspect, in formula (I), R1 is OH, an unsubstituted C1-C6 alkoxy group, a C1-C6 alkoxy group substituted with benzene, or an unsubstituted C2-C6 alkeneoxy group.

[0017] In some embodiments of the first or second aspect, in formula (I), R 1 is OH, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an allyloxy group, or a benzyloxy group.

[0018] In some embodiments of the first or second aspect, in formula (I), R2 is OH, —N(H)—R 15 , N(R 16 )-R 17 , an unsubstituted C1-C6 alkoxy group, or a C1-C6 alkoxy group substituted by benzene, where R 15 is an amino acid residue that does not contain proline, and R 16 and R 17 together form a proline residue.

[0019] In some embodiments of the first or second aspect, in formula (I), R2 is OH, a methoxy group, or —N(H)—R 15 or N(R 16 )-R 17 where R 15 is a glycine residue, an alanine residue, a valine residue, a leucine residue, an isoleucine residue, a methionine residue, a tryptophan residue, a serine residue, a tyrosine residue, a cysteine ​​residue, a phenylalanine residue, an asparagine residue, a glutamine residue, a threonine residue, an aspartic acid residue, a glutamic acid residue, a lysine residue, an arginine residue, or a histidine residue; R 16 and R 17 together form a proline residue.

[0020] In some embodiments of the first or second aspect, in formula (I) above, R2 is OH or a methoxy group.

[0021] In some embodiments of the first or second aspect, in formula (I), R2 is -N(H)-R 15 where R 15is a glycine residue, alanine residue, valine residue, leucine residue, isoleucine residue, methionine residue, tryptophan residue, serine residue, tyrosine residue, cysteine ​​residue, phenylalanine residue, asparagine residue, glutamine residue, threonine residue, aspartic acid residue, glutamic acid residue, lysine residue, arginine residue, or histidine residue.

[0022] In some embodiments of the first or second aspect, in formula (I), R2 is -N(H)-R 15 where R 15 is a threonine residue.

[0023] In some embodiments of the first or second aspect, the amino acid may be in the L- or D-form.

[0024] In some embodiments of the first or second aspect, in formula (I), R2 is -N(H)-R 15 where R 15 is an L-threonine residue.

[0025] In some embodiments of the first or second aspect, in formula (I), R3 and R4 are each independently an unsubstituted or substituted C1-C6 alkanoyl group, and the substituted C1-C6 alkanoyl group means that one or more hydrogen atoms in the C1-C6 alkanoyl group are substituted with a group selected from the group consisting of a halogen, a nitro group, a cyano group, an acetyl group, a propionyl group, and a phenyl group.

[0026] In some embodiments of the first or second aspect, in formula (I), R3 and R4 are each independently an acetyl group or a trifluoroacetyl group.

[0027] In some embodiments of the first or second aspect, in formula (I), R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 13are each independently a hydrogen atom, an unsubstituted C1-C6 alkanoyl group, a C1-C6 alkanoyl group substituted with benzene, or a substituted phenylmethyl group.

[0028] In some embodiments of the first or second aspect, in formula (I), R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 13 are each independently hydrogen, an acetyl group, a benzyl group, or a 4-methoxybenzyl group.

[0029] In some embodiments of the first or second aspect, in formula (I), R 14 is OH or an unsubstituted or substituted C1-C6 alkoxy group.

[0030] In some embodiments of the first or fourteenth aspect, in formula (I), R2 is OH or a methoxy group.

[0031] In some embodiments of the first or second aspect, in formula (I), R 1 is OH, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an allyloxy group, or a benzyloxy group.

[0032] R2 is OH, methoxy group or -N(H)-R 15 where R 15 is a threonine residue, R3 and R4 each independently represent an acetyl group or a trifluoroacetyl group; R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 13 are each independently hydrogen, an acetyl group, a benzyl group, or a 4-methoxybenzyl group, and R 14 is an OH or methoxy group.

[0033] In one embodiment of the first or second aspect, in formula (I), R1 is an n-propoxy group, an allyloxy group, or a benzyloxy group; R2 is OH or -N(H)-R 15 where R 15 is a threonine residue, R3 and R4 are each independently an acetyl group; R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 13 are each independently hydrogen, and R 14 is OH.

[0034] In one embodiment of the first or second aspect, in formula (I), R1 is OH; R2 is OH or -N(H)-R 15 where R 15 is a threonine residue, R3 and R4 are each independently an acetyl group; R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 13 are each independently hydrogen, and R 14 is OH.

[0035] In one embodiment of the first or second aspect, in formula (I), R1 is a methoxy group, R2 is OH or -N(H)-R 15 where R 15 is a threonine residue, R3 and R4 are each independently an acetyl group; R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 13 are each independently hydrogen, and R 14 is OH.

[0036] In one embodiment of the first or second aspect, in formula (I), R1 is an ethoxy group, R2 is OH or -N(H)-R 15 where R 15 is a threonine residue, R3 and R4 are each independently an acetyl group; R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 13 are each independently hydrogen, and R 14 is OH.

[0037] In one embodiment of the first or second aspect, in formula (I), R1 is an isopropoxy group, R2 is OH or -N(H)-R 15 where R 15 is a threonine residue, R3 and R4 are each independently an acetyl group; R5, R6, R7, R8, R9, R 10 , R 11 , R 12 and R 13 are each independently hydrogen, and R 14 is OH.

[0038] In some embodiments of the first or second aspect, the use of the bacterial capsular oligosaccharide derivatives described herein is for their anti-inflammatory activity or as a method for preventing or treating inflammation, and can suppress the production of nitric oxide and prostaglandin E2, and / or inhibit the expression of nitric oxide synthase and cyclooxidase 2 proteins, and / or reduce the release of interleukin-1β, interleukin-6, and tumor necrosis factor-α.

[0039] In some embodiments of the first or second aspect, the use of the bacterial capsular oligosaccharide derivatives or the method of preventing or treating inflammation according to the present application is to treat sepsis, wherein the sepsis includes pyosepsis.

[0040] Septicemia is a life-threatening clinical syndrome characterized by organ dysfunction due to the body's overreaction to infection. Clinically, it is common for bacteria to enter the bloodstream after surgery, wounds, or when the immune system is weakened, and then grow and multiply there, producing toxins that cause severe systemic infection. Symptoms include fever, severe toxic blood, skin rash, enlarged liver and spleen, and increased white blood cell count.

[0041] In some embodiments of the third aspect, the present application provides a method for producing the bacterial capsular oligosaccharide derivatives described above, the method comprising: The process includes the steps of reacting a compound of formula (I-13) with a compound of formula (I-18) to obtain compound (I-19), reacting a compound of formula (I-13-Me) with a compound of formula (I-18) to obtain compound (I-19-Me), reacting a compound of formula (I-13-Et) with a compound of formula (I-18) to obtain compound (I-19-Et), and reacting a compound of formula (I-13-Pr) with a compound of formula (I-18) to obtain compound (I-19-Pr). [ka] Here, in formula (I-13), formula (I-13-Me), formula (I-13-Et), formula (I-13-Pr), formula (I-18), formula (I-19), formula (I-19-Me), formula (I-19-Et), formula (I-19-Et) or formula (I-19-Pr), Ac is an acetyl group, Ph is a phenyl group, Bn is a benzyl group, Me is a methyl group, Et is an ethyl group, Pr is an isopropyl group, TFA is a trifluoroacetyl group, and Lev is an acetylpropionyl group.

[0042] In some embodiments of the third aspect, the compounds of formula (I-13), formula (I-13-Me), formula (I-13-Et), and formula (I-13-Pr) can be prepared using the following route: [ka] [ka] In the above pathway, the substituent PMB is a p-methoxybenzyl group and Tol is a p-tolyl group.

[0043] In some embodiments of the third aspect, the compound of formula (I-18) can be prepared starting from sodium hyaluronate using the following route: [ka]

[0044] In some embodiments of the third aspect, the method for producing a bacterial capsular oligosaccharide derivative further comprises obtaining a compound of formula (I-19), (I-19-Me), (I-19-Et) or (I-19-Pr), followed by selectively treating the Lev group, followed by an amidation reaction with a protected amino acid, and finally completely removing the protecting group to obtain a compound of formula (I) that is free of protecting groups; or alternatively, obtaining a compound of formula (I-19), (I-19-Me), (I-19-Et) or (I-19-Pr), followed by completely removing the protecting group to obtain a compound of formula (I) that is free of protecting groups. [ka]

[0045] In some embodiments of the fourth aspect, the present application provides novel bacterial capsular oligosaccharide derivatives having formula (I'), or pharmaceutically acceptable salts, solvates, or prodrugs thereof: [ka] In formula (I'), R1' is hydrogen, an unsubstituted or substituted C1-C6 alkoxy group, an unsubstituted or substituted C2-C6 alkenoxy group, an unsubstituted or substituted C2-C6 alkynyloxy group, an unsubstituted or substituted C1-C6 alkylthio group, an unsubstituted or substituted C1-C6 alkanoyloxy group, or an unsubstituted or substituted areneoxy group, wherein the substituted C1-C6 alkoxy group, substituted C2-C6 alkenoxy group, substituted C2-C6 The terms "6 alkynyloxy group, substituted C1-C6 alkylthio group, substituted C1-C6 alkanoyloxy group and substituted areneoxy group" mean that one or more hydrogen atoms in a C1-C6 alkoxy group, C2-C6 alkenoxy group, C2-C6 alkynyloxy group, C1-C6 alkylthio group, C1-C6 alkanoyloxy group or areneoxy group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkoxy group, a halogen atom, a nitro group, a cyano group, an acetyl group, a propionyl group and a phenyl group, R2' is OH, -N(H)-R 15 , N(R 16 )-R 17 , an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group, wherein R 15 is an amino acid residue that does not contain proline, and R 16 and R 17 together form a proline residue, and the substituted C1-C6 alkoxy group and substituted areneoxy group mean that one or more hydrogen atoms in the C1-C6 alkoxy group or areneoxy group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkoxy group, a halogen atom, a nitro group, a cyano group, and a phenyl group; R3' and R4' each independently represent an unsubstituted or substituted C1-C6 alkanoyl group, wherein the substituted C1-C6 alkanoyl group means that one or more hydrogen atoms in the C1-C6 alkanoyl group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkanoyl group, a halogen atom, a nitro group, a cyano group, an acetyl group, a propionyl group, and a phenyl group; R5', R6', R7', R8', R9', R 10 ', R 11 ', R 12 ' and R 13 each ' is independently hydrogen or an unsubstituted or substituted C1-C6 alkanoyl group, wherein the substituted C1-C6 alkanoyl group means that one or more hydrogen atoms in the C1-C6 alkanoyl group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkanoyl group, halogen, a nitro group, a cyano group, an acetyl group, a propionyl group, and a phenyl group; R 14 ' is OH, an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group, wherein the substituted C1-C6 alkoxy group and substituted areneoxy group mean that one or more hydrogen atoms in the C1-C6 alkoxy group or areneoxy group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkoxy group, a halogen atom, a nitro group, a cyano group, and a phenyl group; In formula (I'), R1' is not an n-propoxy group or an allyloxy group.

[0046] In some embodiments of the fourth aspect, in formula (I'), R 1' is OH, a methoxy group, an ethoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a t-butoxy group, or a benzyloxy group.

[0047] In some embodiments of the fourth aspect, in formula (I'), R1' is OH.

[0048] In some embodiments of the fourth aspect, in formula (I'), R1' is a methoxy group.

[0049] In some embodiments of the fourth aspect, in formula (I'), R1' is an ethoxy group.

[0050] In some embodiments of the fourth aspect, in formula (I'), R1' is an isopropoxy group.

[0051] In some embodiments of the fourth aspect, in formula (I′), R2′ is OH, —N(H)—R 15 , N(R 16 )-R 17 , an unsubstituted C1-C6 alkoxy group, or a C1-C6 alkoxy group substituted by benzene, where R 15 is an amino acid residue that does not contain proline, and R 16 and R 17 together form a proline residue.

[0052] In some embodiments of the fourth aspect, in formula (I′), R2′ is OH, a methoxy group, —N(H)—R 15 or N(R 16 )-R 17 where R 15 is a glycine residue, an alanine residue, a valine residue, a leucine residue, an isoleucine residue, a methionine residue, a tryptophan residue, a serine residue, a tyrosine residue, a cysteine ​​residue, a phenylalanine residue, an asparagine residue, a glutamine residue, a threonine residue, an aspartic acid residue, a glutamic acid residue, a lysine residue, an arginine residue, or a histidine residue; R 16 and R 17 together form a proline residue.

[0053] In some embodiments of the fourth aspect, in formula (I'), R2' is OH or a methoxy group.

[0054] In some embodiments of the fourth aspect, in formula (I′), R2′ is —N(H)—R 15 where R15 is a glycine residue, alanine residue, valine residue, leucine residue, isoleucine residue, methionine residue, tryptophan residue, serine residue, tyrosine residue, cysteine ​​residue, phenylalanine residue, asparagine residue, glutamine residue, threonine residue, aspartic acid residue, glutamic acid residue, lysine residue, arginine residue, or histidine residue.

[0055] In some embodiments of the fourth aspect, in formula (I′), R2′ is —N(H)—R 15 where R 15 is a threonine residue.

[0056] In some embodiments of the fourth aspect, the amino acid may be in the L- or D-form.

[0057] In some embodiments of the fourth aspect, in formula (I′), R2′ is —N(H)—R 15 where R 15 is an L-threonine residue.

[0058] In some embodiments of the fourth aspect, in formula (I'), R3' and R4' are each independently an unsubstituted or substituted C1-C6 alkanoyl group, and the substituted C1-C6 alkanoyl group means that one or more hydrogen atoms in the C1-C6 alkanoyl group are substituted with a group selected from the group consisting of a halogen, a nitro group, a cyano group, an acetyl group, a propionyl group, and a phenyl group.

[0059] In some embodiments of the fourth aspect, in formula (I'), R3' and R4' are each independently an acetyl group or a trifluoroacetyl group.

[0060] In some embodiments of the fourth aspect, in formula (I′), R5′, R6′, R7′, R8′, R9′, R 10 ', R 11 ', R 12 ' and R 13Each ' is independently hydrogen, an unsubstituted C1-C6 alkanoyl group, a C1-C6 alkanoyl group substituted with benzene, or a substituted phenylmethyl group.

[0061] In some embodiments of the fourth aspect, in formula (I′), R5′, R6′, R7′, R8′, R9′, R 10 ', R 11 ', R 12 ' and R 13 Each ' is independently hydrogen, an acetyl group, a benzyl group, or a 4-methoxybenzyl group.

[0062] In some embodiments of the fourth aspect, in formula (I′), R 14 ' is OH or an unsubstituted or substituted C1-C6 alkoxy group.

[0063] In some embodiments of the fourth aspect, in formula (I′), R 14 ' is an OH or methoxy group.

[0064] In some embodiments of the fourth aspect, in formula (I'): R 14 'OH , a methoxy group, an ethoxy group, or an isopropoxy group; R2' is OH, a methoxy group, or -N(H)-R 15 where R 15 is a threonine residue, R3′ and R4′ are each independently an acetyl group or a trifluoroacetyl group; R5', R6', R7', R8', R9', R 10 ', R 11 ', R 12 ' and R 13 ' are each independently hydrogen, an acetyl group, a benzyl group, or a 4-methoxybenzyl group, and R 14 ' is an OH or methoxy group.

[0065] In one embodiment of the fourth aspect, in formula (I'), R1' is OH, R2' is OH; R3′ and R4′ are each independently an acetyl group; R5', R6', R7', R8', R9', R 10 ', R 11 ', R 12 ' and R 13 ' are each independently hydrogen, and R 14 ' is OH, That is, formula (I') is compound CP-1. [ka]

[0066] In one embodiment of the fourth aspect, in formula (I'), R1' is OH, R2' is -N(H)-R 15 where R 15 is a threonine residue, R3′ and R4′ are each independently an acetyl group; R5', R6', R7', R8', R9', R 10 ', R 11 ', R 12 ' and R 13 ' are each independently hydrogen, and R 14 ' is OH, That is, formula (I') is compound CP-2. [ka]

[0067] In one embodiment of the fourth aspect, in formula (I'), R1' is a methoxy group, R2' is OH; R3′ and R4′ are each independently an acetyl group; R5', R6', R7', R8', R9', R 10 ', R 11 ', R 12 ' and R13 ' are each independently hydrogen, and R 14 ' is OH, That is, formula (I') is the compound CP-Me. [ka]

[0068] In one embodiment of the fourth aspect, in formula (I'), R1' is an ethoxy group, R2' is OH; R3′ and R4′ are each independently an acetyl group; R5', R6', R7', R8', R9', R 10 ', R 11 ', R 12 ' and R 13 ' are each independently hydrogen, and R 14 ' is OH, That is, formula (I') is the compound CP-Et. [ka]

[0069] In one embodiment of the fourth aspect, in formula (I'), R1' is an isopropoxy group, R2' is OH; R3′ and R4′ are each independently an acetyl group; R5', R6', R7', R8', R9', R 10 ', R 11 ', R 12 ' and R 13 ' are each independently hydrogen, and R 14 ' is OH, That is, formula (I') is the compound CP-Pr. [ka]

[0070] In some embodiments of the fifth aspect, the present application provides a pharmaceutical composition comprising the novel bacterial capsular oligosaccharide derivative. The pharmaceutical composition according to the present invention may be in the form of a formulation for oral or non-gastrointestinal administration, and the dosage may be 0.1 to 5000 mg / dose / day.

[0071] In some embodiments of the first, second, sixth, seventh, or eighth aspects, the novel bacterial capsular oligosaccharide derivatives or pharmaceutical compositions thereof according to the present application have anti-inflammatory activity or can be used in methods for preventing or treating inflammation, by suppressing the production of nitric oxide and prostaglandin E2, and / or inhibiting the expression of nitric oxide synthase and cyclooxidase 2 proteins, and / or reducing the release of interleukin-1β, interleukin-6, and tumor necrosis factor-α.

[0072] In some embodiments of the first, second, sixth, seventh, or eighth aspects, the novel bacterial capsular oligosaccharide derivatives or pharmaceutical compositions thereof according to the present application have anti-inflammatory activity or can be used in methods for preventing or treating inflammation, by suppressing the production of nitric oxide and prostaglandin E2, and / or inhibiting the expression of nitric oxide synthase and cyclooxidase 2 proteins, and / or reducing the release of interleukin-1β, interleukin-6, and tumor necrosis factor-α.

[0073] In some embodiments of the first, second, sixth, seventh, or eighth aspect, the use of the novel bacterial capsular oligosaccharide derivative or pharmaceutical composition thereof according to the present application is the treatment of sepsis, or the method for preventing or treating inflammation is the treatment of sepsis, wherein the sepsis includes pyosepsis.

[0074] Other features and advantages of the present application will be set forth in the description which follows, and in part will be obvious from the description, or may be learned by the practice of the present application. Other advantages of the present application will be realized and obtained by the embodiments set forth in the description and drawings.

[0075] Specific Embodiments In order to make the purpose, technical solution and advantages of the present application clearer, the following detailed description of the embodiments of the present invention is provided, and the features of the embodiments can be arbitrarily combined with each other unless there is a conflict.

[0076] Abbreviation Ac is an acetyl group. PE is petroleum ether. EtOAc is ethyl acetate. CDCl3 is deuterated chloroform. DCM is dichloromethane. MeOH is methanol. TLC is thin layer chromatography. IL-1β is interleukin-1β. IL-6 is interleukin-6. TNF-α is tumor necrosis factor-α. LPS is lipopolysaccharide. PEG2 is prostaglandin E2. NO is nitric oxide. iNOS is the human nitric oxide synthase. COX-2 is cyclooxidase 2. Dex is dexamethasone.

[0077] Example 1 Synthesis of p-tolyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranose [ka] Peracetylgalactose (5.0 g, 12.8 mmol) and p-trithiophenol (1.75 g, 14.1 mmol, 1.1 equiv.) were dissolved in dichloromethane (50.0 mL), cooled to 0°C, and boron trifluoride ethyl etherate (4.0 mL, 32.0 mmol, 2.5 equiv.) was added. The mixture was allowed to react at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed successively with saturated sodium bicarbonate and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography (petroleum ether / EtOAc 2:1) to give a white solid (5.76 g, 99%). f = 0.22 (petroleum ether / EtOAc 2:1); 1 H NMR (400 MHz, CDCl3, TMS) δ 7.41 (2H, d, aromatic, J = 8.1 Hz), 7.13 (2H, d, aromatic, J = 7.9 Hz ), 5.41 (1H, d, H-4, J = 2.9 Hz), 5.22 (1H, t, H-2, J = 10.0 Hz), 5.04 (1H, dd, H-3, J = 3.3 Hz, J = 10.0 Hz), 4.65 (1H, d, H-1, J = 9.9 Hz), 4.19 (1H, dd, H-6a, J = 6.9 Hz, J = 11.3 Hz), 4.11 (1H, dd, H-6b, J = 6.4 Hz, J = 11.4 Hz), 3.91 (1H, t, H-5, J = 6.9 Hz), 2.35 (3H, s, CH3of STol), 2.12 (3H, s, COCH3), 2.10 (3H, s, COCH3), 2.04 (3H, s, COCH3), 1.97 (3H, s, COCH3); 13 C NMR (100 MHz, CDCl3, TMS) δ 170.4, 170.2, 170.0, 169.4, 138.5, 133.2, 129.6, 128.6, 87.0, 74.4, 72.0, 67.3, 67.2, 61.6, 21.2, 20.9, 20.7, 20.6, 20.5.

[0078] Synthesis of p-tolyl 4,6-O-benzenemethylene-1-thio-β-D-galactopyranose [ka] p-Tolyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranose (5.0 g, 11.0 mmol) was dissolved in methanol (50.0 mL), and the pH of the reaction mixture was adjusted to 9-10 with sodium methanol. The mixture was then reacted at room temperature for 1 hour. The reaction mixture was neutralized to pH 7 using IR-120 cation exchange resin, filtered, and the resin was washed with methanol. The filtrate was concentrated. The concentrated crude product and (+)-camphorsulfonic acid (1.28 g, 5.5 mmol, 0.5 equiv.) were dissolved in anhydrous acetonitrile (70.0 mL). Benzaldehyde dimethyl acetal (2.48 mL, 16.5 mmol, 1.5 equiv.) was added, and the mixture was reacted at room temperature overnight. After the reaction was confirmed to be complete by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction, and the reaction solution was concentrated under reduced pressure and purified by column chromatography (DCM / MeOH 30:1) to obtain a white solid (3.87 g, two-step yield 94%). f = 0.40 ( DCM / MeOH 20:1); 1 H NMR (400 MHz, CDCl3, TMS) δ 7.55 (2H, d, aromatic, J = 8.1 Hz), 7.40-7.34 (5H, m, aromatic), 7.08 (2H, d, aromatic, J = 8.1 Hz), 5.44 (1H, s), 4.39 (1H, d, J = 9.1 Hz), 4.31 (1H, dd, J = 1.0 Hz, J = 12.4 Hz), 4.07 (1H, d, J = 1.6 Hz), 3.93 (1H, dd, J = 1.4 Hz, J = 12.4 Hz), 3.60 (2H, d, J = 6.6 Hz), 3.39 (1H, s), 3.09 (1H, d, J = 7.6 Hz), 3.07 (1H, s), 2.34 (3H, s, CH3of STol); 13C NMR (100 MHz, CDCl3, TMS) δ 138.3, 137.8, 134.2, 129.7, 129.3, 128.2, 127.0, 126.7, 101.3, 87.0, 75.5, 73.6, 69.9, 69.3, 21.3.

[0079] Synthesis of p-tolyl 3-O-benzyl-4,6-O-benzenemethylene-1-thio-β-D-galactopyranose [ka] p-Tolyl 4,6-O-benzenemethylene-1-thio-β-D-galactopyranose (3.50 g, 9.35 mmol) and dibutyltin oxide (2.79 g, 11.2 mmol, 1.2 equiv.) were dissolved in anhydrous toluene (50 mL) and reacted at 120 °C for 8 hours. The mixture was cooled to room temperature, concentrated under reduced pressure to remove the solvent, and the resulting intermediate was dried in vacuo for 1 hour. The intermediate and tetrabutylammonium bromide (4.52 g, 14.0 mmol, 1.5 equiv.) were dissolved in anhydrous toluene (30 mL), and benzyl bromide (1.66 mL, 14.0 mmol, 1.5 equiv.) were added. The mixture was reacted at 60 °C for 12 hours. After the completion of the reaction was detected by TLC, the reaction solution was diluted with ethyl acetate, washed successively with 1M hydrochloric acid and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography (Toluene / EtOAc 9:1) to give a white solid (4.08 g, 94%). f = 0.30 (petroleum ether / EtOAc 2:1); 1H NMR (400 MHz, CDCl3, TMS) δ 7.57 (2H, d, aromatic, J = 8.1 Hz), 7.26-7.41 (10H, m, aromatic), 7.05 (2H, d, aromatic, J = 8.1 Hz), 5.41 (1H, s, PhCH), 4.71 (2H, d, PhCH2, J = 2.0 Hz), 4.46 (1H, d, H-1, J = 9.4 Hz), 4.34 (1H, dd, H-6a, J = 1.6 Hz, J = 12.3 Hz), 4.12 (1H, d, H-4, J = 3.3 Hz), 3.96 (1H, dd, H-6b, J = 1.7 Hz, J = 12.3 Hz), 3.87 (1H, t, H-2, J = 9.4 Hz), 3.50 (1H, dd, H-3, J = 3.3 Hz, J = 9.3 Hz), 3.43 (1H, d, H-5, J = 0.9 Hz), 2.45 (1H, s, OH), 2.33 (3H, s, CH3of STol); 13 C NMR (100 MHz, CDCl3, TMS) δ 138.4, 138.0, 137.9, 134.4, 129.7, 129.0, 128.5, 128.1, 128.0, 126.6, 126.5, 101.2, 87.1, 80.2, 73.3, 71.7, 70.0, 69.4, 67.1, 21.2. ESI-Q-TOF (positive mode) calculated value C 27 H 32 NO5S + [M+NH4] + m / z 482.2001, measured value 482.1999.

[0080] Synthesis of p-tolyl 2-Op-methoxybenzyl-3-O-benzyl-4,6-O-benzenemethylene-1-thio-β-D-galactopyranose [ka] p-Tolyl 3-O-benzyl-4,6-O-benzenemethylene-1-thio-β-D-galactopyranose (2.60 g, 5.60 mmol) was dissolved in anhydrous N,N-dimethylformamide (50 mL). Sodium hydride (60%, 448 mg, 11.2 mmol, 2.0 equiv.) was added batchwise under ice-bath conditions, followed by p-methoxybenzyl chloride (1.52 mL, 11.2 mmol, 2.0 equiv.). The mixture was then cooled to room temperature and stirred for 2 hours. After TLC showed the reaction was complete, the mixture was quenched by adding an appropriate amount of methanol dropwise. The reaction mixture was diluted with ethyl acetate, and the organic phase was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography (petroleum ether / EtOAc 3:1) to give a white solid (3.18 g, 97%). f = 0.38 (petroleum ether / EtOAc 2:1); 1 H NMR (400 MHz, CDCl3, TMS) δ 7.61-7.59,7.51-7.50,7.35-7.25,6.98-6.96,6.86-6.84 (18H, m, aromatic), 5.43 (1H, s, PhCH), 4.67 (2H, s, 2PhCH2), 4.63 (2H, s, 2PhCH2), 4.52 (1H, d, H-1, J = 9.4 Hz),4.28 (1H, d, H-6a, J = 12.1 Hz), 4.07 (1H, d, H-4, J = 2.9 Hz), 3.89 (1H, s, H-6b), 3.82 (1H, t, H-2, J = 9.2 Hz), 3.74 (3H, s, OCH3), 3.56 (1H, dd, H-3, J = 2.4 Hz,J = 8.8 Hz),3.26 (1H, s, H-5),2.26 (3H, s, CH3of STol); 13C NMR (100 MHz, CDCl3, TMS) δ 159.4, 138.4, 138.2, 137.7, 133.4, 131.0, 129.9, 129.8, 129.1, 129.0, 128.5, 128.2, 127.9, 126.8, 113.9, 101.3, 86.7, 81.6, 75.3, 75.2, 73.7, 69.8, 69.5, 55.4, 21.3. ESI-Q-TOF (positive mode) calculated value C 35 H 40 NO6S + [M+NH4] + m / z 602.2576, observed value 602.2583.

[0081] Synthesis of p-tolyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-1-thio-β-D-galactopyranose [ka] Under argon gas protection, p-tolyl 2-Op-methoxybenzyl-3-O-benzyl-4,6-O-benzenemethylene-1-thio-β-D-galactopyranose (2.0 g, 3.42 mmol) was dissolved in anhydrous dichloromethane (30.0 mL). 1 M borane tetrahydrofuran solution (17.1 mL, 17.1 mmol, 5.0 equiv.) was added under ice bath conditions. After stirring for 10 minutes, trifluoromethanesulfonic acid trimethylsilylate (93 μL, 0.51 mmol, 0.15 equiv.) was added dropwise. The mixture was then allowed to warm to room temperature and react for 2 hours. After TLC showed completion of the reaction, an appropriate amount of triethylamine was added to quench the reaction. Methanol was added dropwise until hydrogen gas evolution ceased. The mixture was concentrated under reduced pressure and purified by column chromatography (petroleum ether / EtOAc 4:1) to give a white solid (1.81 g, 90%). f = 0.26 (petroleum ether / EtOAc 2:1); 1H NMR (400 MHz, CDCl3, TMS) δ 7.46-7.44, 7.34-7.29, 7.01-6.99, 6.85-6.83 (18H, m, aromatic), 4.94 (1H, d, J = 11.7 Hz), 4.73 (3H, m), 4.66 (1H, d, J = 10.0 Hz), 4.61 (1H, d, J = 11.5 Hz), 4.56 (1H, d, J = 9.4 Hz), 3.89 (1H, t, J = 9.4 Hz), 3.83-3.78 (2H, m), 3.76 (3H, s), 3.57-3.50 (2H, m), 3.39 (1H, t, J = 6.0 Hz), 2.26 (3H, s); 13 C NMR (100 MHz, CDCl3, TMS) δ 159.4, 138.5, 138.3, 137.4, 132.1, 130.6, 130.2, 130.1, 129.7, 128.6, 128.4, 128.2, 127.8, 127.6, 113.8, 88.0, 84.3, 78.9, 77.2, 75.3, 74.3, 73.5, 73.0, 62.2, 55.4, 21.2; ESI-Q-TOF (positive mode) calculated value C 35 H 42 NO6S + [M+NH4] + m / z 604.2733, found 604.2737.

[0082] Synthesis of p-tolyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-1-thio-β-D-galactopyranose [ka] p-Tolyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-1-thio-β-D-galactopyranose (1.80 g, 3.07 mmol) was dissolved in anhydrous dichloromethane (30 mL), and levulinic acid (713 mg, 6.14 mmol, 2.0 equiv), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.18 g, 6.14 mmol, 2.0 equiv), and a catalytic amount of 4-dimethylaminopyridine were added sequentially. The reaction was allowed to proceed at room temperature for 3 hours. After completion of the reaction was confirmed by TLC, the reaction mixture was diluted with dichloromethane, and the organic phase was washed with saturated sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography (petroleum ether / EtOAc 3:1) to give a white solid (12.3 g, 92%). f = 0.30 (petroleum ether / EtOAc 2:1); 1 H NMR (400 MHz, CDCl3, TMS) δ 7.47-7.45, 7.38-7.29, 7.02-7.00, 6.86-6.84 (18H, m, aromatic), 4.98 (1H, d, J = 11.4 Hz, PhCH2), 4.75 (3H, m, PhCH2), 4.67 (1H, d, J = 9.8 Hz, PhCH2), 4.63 (1H, d, J = 11.4 Hz, PhCH2), 4.55 (1H, d, J = 9.6 Hz, H-1), 4.27 (1H, m, H-6a), 4.15 (1H, m, H-6b), 3.89 (2H, m, H-2, H-4), 3.78 (3H, s, OCH3), 3.59-3.55 (2H, m, H-3, H-5), 2.71-2.68, 2.51-2.47 (4H, m, CH2of Lev), 2.29 (3H, s, PhCH3), 2.14 (3H, s, CH3CO); 13C NMR (100 MHz, CDCl3, TMS) δ 206.5, 159.3, 138.5, 138.3, 137.3, 132.2, 130.6, 130.2, 130.0, 129.6, 128.5, 128.3, 128.1, 127.8, HRMS (ESI-MS) Calculated value C 40 H 44 NaO8S + [M+Na] + m / z 707.2649, measured value 707.2635.

[0083] Synthesis of 2-deoxy-2-trifluoroacetylamino-1,3,4,6-tetra-O-acetyl-β-D-galactopyranose [ka] Peracetylgalactosamine (5.0 g, 12.8 mmol) was dissolved in anhydrous pyridine (100 mL), trifluoroacetic anhydride (9.02 mL, 64.0 mmol, 5.0 equiv.) was added, and the mixture was heated to 135 °C and reacted for 1 hour. After the completion of the reaction was detected by TLC, an appropriate amount of methanol was added to quench the reaction. The reaction solution was diluted with dichloromethane, and the organic phase was washed successively with 1 M hydrochloric acid solution and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH 60:1) to obtain a white solid (5.0 g, 88%). f = 0.34(DCM / MeOH 30:1); 1H NMR (400 MHz, CDCl3, TMS) δ 7.19 (1H, d, J = 9.4 Hz, NHAc), 5.80 (1H, d, H-1, J = 8.9 Hz), 5.42 (1H, d, H-4, J = 3.0 Hz), 5.20 (1H, d, H-3, J = 3.2 Hz, J = 11.3 Hz), 4.50 (1H, m, H-2), 4.21-4.07 (3H, m, H-5, H-6a, H-6b), 2.20 (3H, s, CH3CO), 2.14 (3H, s, CH3CO), 2.06 (3H, s, CH3CO), 2.03 (3H, s, CH3CO); 13 C NMR (100 MHz, CDCl3, TMS) δ 170.8, 170.7, 170.2, 169.6, 157.7 (q, J = 37.4 Hz, COCF3), 117.0 (q, J = 285.1 Hz, COCF3), 92.3, 72.0, 69.9, 66.2, 61.4, 50.2, 20.6, 20.5, 20.4. ESI-Q-TOF (positive mode) calculated value C 16 H 24 F3N2O 10 + [M+NH4] + m / z 461.1383, measured 461.1381.

[0084] Synthesis of p-tolyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-1-thio-β-D-galactopyranose [ka] 2-Deoxy-2-trifluoroacetylamino-1,3,4,6-tetra-O-acetyl-β-D-galactopyranose (5.0 g, 11.3 mmol) and p-trithiophenol (2.1 g, 17.0 mmol, 1.5 equiv.) were dissolved in anhydrous dichloromethane (100 mL). Boron trifluoride ethyl ether complex (4.28 mL, 33.9 mmol, 3.0 equiv.) was added dropwise in an ice bath, and the mixture was allowed to react overnight at room temperature. After completion of the reaction was confirmed by TLC, the mixture was quenched with an appropriate amount of triethylamine. The reaction mixture was diluted with dichloromethane, and the organic phase was washed successively with saturated sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give a yellow syrup (5.68 g, 99%). f =0.24 (petroleum ether / EtOAc 2:1) and used directly in the next reaction.

[0085] Synthesis of benzyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-β-D-galactopyranose [ka] Under argon gas protection, p-tolyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-1-thio-β-D-galactopyranose (5.68 g, 11.2 mmol) and 4 Å molecular sieves were dissolved in anhydrous dichloromethane (100 mL), and benzyl alcohol (2.33 mL, 22.4 mmol, 2.0 equiv.) was added. The mixture was stirred at room temperature for 2 hours, then cooled to -40°C. N-iodosuccinimide (3.53 g, 15.7 mmol, 1.4 equiv.) was added, and the mixture was stirred for 15 minutes. Trifluoromethanesulfonic acid (300 μL, 3.36 mmol, 0.3 equiv.) was added dropwise, and the mixture was allowed to react with stirring for 3 hours. After the completion of the reaction was detected by TLC, it was quenched by adding an appropriate amount of triethylamine, filtered through molecular sieves with diatomaceous earth, the cake was washed several times with dichloromethane, the filtrates were combined, concentrated under reduced pressure and purified by column chromatography (petroleum ether / EtOAc 2:1) to give a white solid (5.06 g, 92%).f = 0.19 (petroleum ether / EtOAc 2:1); 1 H NMR (400 MHz, CDCl3, TMS) δ 7.35-7.26 (5H, m, aromatic), 7.01 (1H, br s, NHAc), 5.36 (1H, d, J = 3.0 Hz), 5.20 (1H, dd, J = 11.5 Hz, J = 3.3 Hz), 4.89 (1H, d, J = 12.1 Hz), 4.63 (1H, d, J = 8.4 Hz), 4.61 (1H, d, J = 12.3 Hz), 4.29-4.13 (3H, m), 3.93 (1H, t, J = 6.8 Hz), 2.15 (3H, s), 2.06 (3H, s), 1.92 (3H, s); 13 C NMR (100 MHz, CDCl3, TMS) δ 170.7, 170.6, 170.4, 157.5 (q, J = 37.1 Hz, COCF3), 136.4, 128.5, 128.2, 127.9, 115.6 (q, J = 286.2 Hz, COCF3), 99.0, 70.8, 70.7, 69.7, 66.6, 61.7, 51.5, 20.6, 20.5, 20.4; ESI-Q-TOF (positive mode) calculated value C 21 H 28 F3N2O9 + [M+NH4] + m / z 509.1747, observed value 509.1747.

[0086] Synthesis of benzyl 2-deoxy-2-trifluoroacetylamino-β-D-galactopyranose [ka] Benzyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-β-D-galactopyranose (2.50 g, 5.09 mmol) was dissolved in methanol (50.0 mL), and an appropriate amount of sodium methanol was added to adjust the pH to 9-10. The reaction was allowed to proceed with stirring at room temperature for 2 hours. After the completion of the reaction was detected by TLC, the reaction solution was neutralized to pH 7 by adding cationic resin, filtered, and the filtrate was concentrated under reduced pressure to dryness, yielding a yellow syrup. f =0.45 (DCM / MeOH 30:1) and used directly in the next reaction.

[0087] Synthesis of benzyl 2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, benzyl 2-deoxy-2-trifluoroacetylamino-β-D-galactopyranose (1.80 g, 4.93 mmol) and (+)-camphorsulfonic acid (572 mg, 2.46 mmol, 0.5 equiv.) were dissolved in anhydrous acetonitrile (50.0 mL), and benzaldehyde dimethyl acetal (1.11 mL, 7.40 mmol, 1.5 equiv.) was added. The temperature was raised to 40 °C and the reaction was carried out overnight. After the reaction was confirmed to be complete by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The reaction solution was concentrated under reduced pressure and purified by column chromatography (petroleum ether / EtOAc 2:1) to obtain the compound as a white solid (2.03 g, 91%). f = 0.30 (petroleum ether / EtOAc 1:1); 1H NMR (400 MHz, DMSO-d6) δ 9.26 (1H, d, NH, J = 9.0 Hz), 7.52-7.49, 7.42-7.26 (10H, m, aromatic), 5.63 (1H, s, PhCH), 5.25 (1H, d, OH, J = 6.4 Hz), 4.82 (1H, d, PhCH2, J = 12.5 Hz), 4.58 (1H, d, H-1, J = 8.3 Hz), 4.55 (1H, d, PhCH2, J = 12.3 Hz), 4.17-4.09 (3H, m, H-4, H-6a, H-6b), 3.95 (1H, m, H-2), 3.82 (1H, m, H-3), 3.57 (1H, s, H-5); 13 C NMR (100 MHz, DMSO-d6) δ 157.0 (q, J = 35.6 Hz, COCF3), 138.9, 138.3, 129.2, 128.6, 128.4, 128.0, 127.6, 126.8, 116.5 (q, J = 287.0 Hz, COCF3), 100.6, 100.3, 75.5, 70.4, 69.0, 66.7, 53.2; HRMS (ESI-MS) calculated value C 22 H 22 NNaO6F3 + [M+Na] + m / z 476.1291, observed value 476.1292.

[0088] Benzyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, p-tolyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-1-thio-β-D-galactopyranose (680 mg, 0.99 mmol, 1.5 equiv.) and benzyl 2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (300 mg, 0.66 mmol) were dissolved in anhydrous dichloromethane / N,N- The mixture was dissolved in dimethylformamide (10.0 mL / 2.0 mL), 4Å molecular sieves (1.0 g) were added, and the mixture was stirred at room temperature for 2 hours. After cooling to 0 ° C, N-iodosuccinimide (297 mg, 1.32 mmol, 2.0 equiv.) and silver trifluoromethanesulfonate (51 mg, 0.20 mmol, 0.3 equiv.) were added sequentially. The mixture was stirred at 0 ° C for 2 hours, then the temperature was gradually raised to room temperature and the mixture was allowed to react overnight. After detecting the completion of the reaction by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The molecular sieves were removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure and purified by column chromatography (DCM / MeOH 100:1) to obtain compound I-12 (555 mg, 83%) as a white solid. f = 0.28 (DCM / MeOH 30:1); 1 H NMR (600 MHz, CDCl3, TMS) δ 7.55, 7.44, 7.34-7.25, 6.92, 6.63 (25H, m, aromatic, NH), 5.56 (1H, s, PhCH), 5.23 (1H, d, H-1 Gal , J = 3.5 Hz), 4.94 (2H, m, PhCH2), 4.87 (1H, d, H-1 GalNAc , J = 8.3 Hz), 4.80 (1H, d, PhCH2, J = 11.8 Hz), 4.63 (2H, m, PhCH2), 4.54 (1H, d, PhCH2, J = 11.5 Hz), 4.45-4.38 (5H, m, H-2 GalNAc , H-4 GalNAc , H-6a GalNAc , PhCH2), 4.17 (1H, dd, H-3 GalNAc, J = 3.5 Hz, J = 10.9 Hz), 4.16-4.12 (2H, m, H-6a Gal , H-6b GalNAc ), 4.07 (1H, dd, H-6b Gal , J = 7.8 Hz, J = 11.7 Hz), 4.03 (1H, dd, H-2 Gal , J = 3.5 Hz, J = 9.9 Hz), 3.84 (1H, dd, H-3 Gal , J = 2.7 Hz, J = 9.9 Hz), 3.80 (1H,m,H-4). Gal ), 3.75 (3H, s, OCH3), 3.73 (1H, m, H-5 Gal ), 3.51 (1H, s, H-5 GalNAc ), 2.83-2.78, 2.63-2.58, 2.52-2.49, 2.40-2.34 (4H, m, CH2of Lev), 2.04 (3H, s, CH3CO); 13 C NMR (150 MHz, CDCl3, TMS) δ 208.9, 172.4, 158.8, 157.1 (q, J = 24.2 Hz, COCF3); 128.3, 128.2(2C), 127.9, 127.7(2C), 127.6, 127.5, 126.4, 115.9 (q, J = 191.2 Hz, COCF3); 74.9, 74.5, 73.7, 71.4, 71.3, 70.6, 70.1, 69.4, 66.5, 64.5, 55.2, 52.4, 37.9, 29.7, 27.8; HRMS (ESI-MS) SpecificationC 55 H 58 NNaO 14 F3 + [M+Na] + m / z 1036.3702;

[0089] Benzyl 3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Benzyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-β-D-galactopyranose-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (340 mg, 0.34 mmol) was dissolved in dichloromethane / water (6.0 mL / 0.6 mL), and 2,3-dichloro-5,6-dicyano-p-benzoquinone (154 mg, 0.68 mmol, 2.0 equiv.) was added in batches. The mixture was allowed to react at room temperature for 1 hour. After completion of the reaction was confirmed by TLC, the reaction mixture was diluted with dichloromethane, and the organic phase was washed successively with saturated sodium bicarbonate solution, saturated sodium thiosulfate solution, and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH 60:1) to give a white solid (258 mg, 85%). R f = 0.36 (DCM / MeOH 30:1); 1 H NMR (600 MHz, CDCl3+CD3OD, TMS) δ 7.59, 7.40-7.26 (20H, m, aromatic), 5.64 (1H, s, PhCH), 5.14 (1H, d, H-1 Gal , J = 3.5 Hz), 4.93 (2H, m, PhCH2), 4.83 (1H, d, PhCH2, J = 11.8 Hz), 4.76 (1H, d, H-1 GalNAc , J = 8.6 Hz), 4.62 (2H, m, PhCH2), 4.50 (1H, d, PhCH2, J = 11.4 Hz), 4.42 (2H, m, H-4 GalNAc , H-6a GalNAc ), 4.35 (1H, t, H-2 GalNAc, J = 10.0 Hz), 4.15 (1H, d, H-3 GalNAc , J = 12.2 Hz), 4.09 (3H, m, H-6a Gal , H-6b GalNAc ), 4.03 (1H, dd, H-6b Gal , J = 2.9 Hz, J = 10.8 Hz), 3.73 (2H, m, H-3 Gal ,), 3.60 (1H, dd, H-4 Gal , J = 2.0 Hz, J = 10.0 Hz), 3.52 (1H, s, ), 2.82-2.76, 2.69-2.64, 2.52-2.47, 2.43-2.39 (4H, m, CH2of Lev), 2.07 (3H, s, CH3CO); 13 C NMR (150 MHz, CDCl3+CD3OD, TMS) δ 209.5, 172.6, 158.2 (q, J = 24.5 Hz, COCF3), 138.5, 138.2, 137.3, 137.2, 129.2, 128.5, 128.4, 128.3, 127.9, 128.4, 128.3, 127.9(2C), 127.7, 126.4, 116.0 (q, J = 190.9 Hz, COCF3), 101.1, 99.0, 95.2, 79.2, 75.1, 74.8, 73.8, 73.0, 70.6, 70.4, 70.1, 69.3, 68.9, 66.6, 63.9, 51.5, 38.0, 29.8, 27.7; HRMS (ESI-MS) calculated value C 47 H 50 NNaO 13 F3 + [M+Na] + m / z 916.3126, observed value 916.3132.

[0090] Synthesis of methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid (1→3)-1,4,6-tris-O-acetyl-2-deoxy-2-acetylamino-α,β-D-glucopyranose [ka] 5.0 g of hyaluronic acid (MW = 500 kDa) was dissolved in 300.0 mL of deionized water and allowed to swell overnight. Concentrated hydrochloric acid (12 M, 13.0 mL, final concentration 0.5 M) was slowly added dropwise and the mixture was heated at 80 °C for 2 days. After completion of the reaction was confirmed by TLC, solid sodium bicarbonate was added to adjust the pH to 7.0. The reaction mixture was concentrated under reduced pressure to a volume of approximately 20.0 mL. The mixture was then slowly added dropwise to 1000.0 mL of ethanol, yielding a light brown flocculent precipitate. The precipitate was filtered under reduced pressure and dried in an infrared oven to yield a yellow powdery solid. The crude product was dissolved in 200.0 mL of 0.02 M hydrochloric acid-methanol solution and allowed to react at 4 °C for 4 days. After completion of the reaction was confirmed by TLC, triethylamine was added to adjust the pH to 7.0, the mixture was concentrated under reduced pressure, and the mixture was extracted three times with toluene to yield a brown powdery solid. The brown powdery solid was dissolved in pyridine (100.0 mL), and acetic anhydride (50.0 mL) was slowly added dropwise under ice bath conditions. The mixture was allowed to warm to room temperature overnight. After detecting the completion of the reaction by TLC, an appropriate amount of methanol was added dropwise under ice bath conditions to quench the reaction. The reaction solution was concentrated under reduced pressure, diluted with dichloromethane, washed with 1M hydrochloric acid solution, and back-extracted three times with dichloromethane. The combined organic phases were washed with saturated sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (DCM / MeOH 60:1, 0.1% triethylamine) to give a pale yellow solid (2.60 g) (α / β=2.5 / 1). f =0.40 (DCM / MeOH 20:1). The NMR spectrum of the mixture is shown in the Appendix, and the ratio of end group isomers is 1 The value was confirmed by H NMR. The calculated value by ESI-Q-TOF (positive mode) was C 27 H 41 N2O 18 + [M+NH4] + The m / z is 681.2354, and the observed value is 681.2360.

[0091] Synthesis of methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid (1→3)-1,4,6-tris-O-acetyl-2-deoxy-2-trifluoroacetamino-α-D-glucopyranose [ka] Methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid (1→3)-1,4,6-tris-O-acetyl-2-deoxy-2-acetylamino-α,β-D-glucopyranose (500 mg, 0.75 mmol) was dissolved in anhydrous pyridine (3.0 mL), trifluoroacetic anhydride (425 μL, 3.01 mmol, 4.0 equiv.) was added, and the mixture was refluxed at 135°C for 30 minutes. After completion of the reaction was confirmed by TLC, the reaction was quenched by adding an appropriate amount of methanol under ice-bath conditions. The reaction mixture was concentrated under reduced pressure, diluted with dichloromethane, washed with 1 M hydrochloric acid solution, and back-extracted three times with dichloromethane. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (PE / acetone 4:1) to give a brown solid (468 mg, 87%). f =0.36 (PE / acetone 1:1). 1 H NMR (400 MHz, CDCl3) δ 6.95 (1H, s, NH), 6.08 (1H, d, H-1 GlcNAc , J = 3.3 Hz), 5.16-5.03 (3H, m, H-3 GlcA , H-5 GlcA , H-4 GlcNAc ), 4.84 (1H, t, H-2 GlcA , J = 8.0 Hz), 4.66 (1H, d, H-1 GlcA , J = 7.8 Hz), 4.43 (1H, m, H-2 GlcNAc ), 4.18 (1H, dd, H-6a GlcNAc , J = 3.7 Hz, J = 12.5 Hz), 4.11-3.98 (4H, m, H-6b GlcNAc , H-3 GlcNAc , H-5GlcNAc , H-4 GlcA ), 3.70 (3H, s, OCH3), 2.15 (3H, s, CH3CO), 2.09 (3H, s, CH3CO), 2.05 (3H, s, CH3CO), 1.97 (6H, s, 2CH3CO), 1.94 (3H, s, CH3CO); 13 C NMR (100 MHz, CDCl3) δ 171.0, 170.1, 169.7, 169.6, 169.3, 168.6, 166.9, 157.2 (q, J = 39.6 Hz, COCF3), 115.7 (q, J = 286.3 Hz, COCF3), 100.1, 90.3, 75.5, 72.4, 72.0, 71.0, 70.0, 69.4, 67.5, 61.7, 52.8, 52.2, 20.8, 20.7, 20.5(2C), 20.3, 20.2; ESI-Q-TOF (positive mode) Calculated value C 27 H 38 F3N2O 18 + [M+NH4] + m / z 735.2072, measured value 735.2081.

[0092] Synthesis of methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid (1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-α,β-D-glucopyranose [ka] Methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid (1→3)-1,4,6-tris-O-acetyl-2-deoxy-2-trifluoroacetylamino-α-D-glucopyranose (400 mg, 0.56 mmol) was dissolved in tetrahydrofuran (6.0 mL) and 3-dimethylaminopropylamine (348 μL, 2.79 mmol, 5.0 equiv.) was added dropwise. The mixture was incubated at room temperature for 1 hour. After completion of the reaction as determined by TLC, the reaction mixture was diluted with dichloromethane, washed with 1 M hydrochloric acid, and back-extracted three times with dichloromethane. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was used directly in the next reaction without further purification.

[0093] Synthesis of 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl ester -(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetamino-D-glucopyranose [2,1,-d] 2-oxazoline [ka] Under argon gas protection, 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-α,β-D-glucopyranose was dissolved in anhydrous acetonitrile (10.0 mL), anhydrous methanesulfonic acid (293 mg, 1.68 mmol) was added, and the mixture was allowed to react at room temperature for 25 minutes. After that, triethylamine (1.55 mL, 11.2 mmol) was added, and the mixture was allowed to react at room temperature for 2 hours. After the reaction was complete by TLC, the reaction mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate solution, and back-extracted three times with dichloromethane. The combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The product was purified by column chromatography (PE / acetone 3:1) to give a white solid (284 mg, 77% yield for the two steps). f =0.49 (PE / acetone 1:1). 1H NMR (400 MHz, CDCl3) δ 6.26(1H,d,H-1). GlcNAc , J = 7.6 Hz), 5.27-5.16(3H, m, H-3 GlcA , H-4 GlcA , H-4 GlcNAc ), 4.97 (1H, t, H-2 GlcA , J = 7.9 Hz), 4.87(1H,d,H-1). GlcA , J = 7.9 Hz), 4.26(1H,d,H-2). GlcNAc , J = 7.3 Hz), 4.18(3H,m,H-3). GlcNAc , H-6a GlcNAc , H-6b GlcNAc ), 4.11 (1H, d, H-5 GlcA , J = 9.6 Hz), 3.72(3H,s,OCH3), 3.65(1H,m,H-5). GlcNAc ), 2.07 (3H, s, CH3CO), 2.04 (3H, s, CH3CO), 2.02 (3H, s, CH3CO), 2.00 (3H, s, CH3CO), 1.99 (3H, s, CH3CO); 13 C NMR (100 MHz, CDCl3) δ 170.7, 170.1, 169.8, 169.4, 169.2, 166.9, 156.3 (q, J = 40.9 Hz, COCF3), 116.0 (q, J = 273.1 Hz, COCF3), 102.9. 100.9, 76.7, 72.4, 72.1, 71.2, 69.1, 68.8, 67.1, 64.8, 63.4, 53.0, 20.8, 20.7(2C), 20.6(2C); HRMS (ESI-MS) SpecificationC 25 H 30 NNaO 16 F3 + [M+Na] + m / z 680.1409;

[0094] Synthesis of methyl benzyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronate, (1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyranose, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetamino-D-glucopyranose[2,1,-d]2-oxazoline (140 mg, 0.21 mmol, 1.5 equiv.) and benzyl 3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetamino) were mixed. Oroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (127 mg, 0.14 mmol) was dissolved in anhydrous dichloromethane (2.0 mL), 4 Å molecular sieves (200 mg) were added, and the mixture was stirred at room temperature for 2 hours, then cooled to -20°C. Trifluoromethanesulfonic acid trimethylsilylate (7.6 μL, 0.042 mmol, 0.3 equiv.) was added, and the mixture was stirred at -20°C for 2 hours, then allowed to warm slowly to room temperature and react overnight. After detecting the completion of the reaction by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The molecular sieves were removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure and purified by column chromatography (PE / acetone 2:1) to give a white solid (195 mg, 90%). f = 0.39 (PE / acetone 1:1); 1H NMR (600 MHz, CDCl3, TMS) δ 8.08 (1H, s, NH), 7.88 (1H, d, NH, J = 9.4 Hz), 7.62, 7.46-7.41, 7.36-7.25, 7.15 (20H, m, aromatic), 5.62 (1H, s, PhCH), 5.16 (1H, t, H-4 GlcA , J = 9.6 Hz), 5.10 (1H, d, H-1 Gal , J = 3.6 Hz), 5.07 (1H, t, H-3 GlcA , J = 9.4 Hz), 4.98-4.94 (3H, m, H-2 GlcA , H-1 GlcNAc , PhCH2), 4.80 (1H, d, PhCH2, J = 11.6 Hz), 4.72 (1H, d, H-1 GalNAc , J = 8.3 Hz), 4.67 (1H, d, PhCH2, J = 12.0 Hz), 4.62 (3H, m, H-3 GlcNAc , H-4 GlcNAc , PhCH2), 4.54 (1H, q, H-2 GalNAc , J = 9.4 Hz), 4.45 (1H, d, H-4 GalNAc , J = 3.2 Hz), 4.40-4.36 (3H, m, H-6a GalNAc , H-6a GlcNAc , H-1 GlcA ), 4.30 (1H, d, PhCH2, J = 12.0 Hz), 4.27 (1H, d, PhCH2, J = 11.7 Hz), 4.16 (1H, m, H-6b GalNAc ), 4.13 (1H, dd, H-6a Gal , J = 2.1 Hz, J = 11.9 Hz), 4.08 (1H, dd, H-2 Gal , J = 3.6 Hz, J = 10.2 Hz), 3.93 (2H, m, H-5 GlcA , H-3 GalNAc ), 3.88 (1H, dd, H-6b GlcNAc, J = 2.1 Hz, J = 12.2 Hz), 3.83 (1H, m, H-6b Gal ), 3.71 (3H, s, OCH3), 3.70 (1H, dd, H-3 Gal , J = 2.8 Hz, J = 10.5 Hz), 3.63 (1H, d, H-5 Gal , J = 8.3 Hz), 3.58 (1H, m, H-5 GlcNAc ), 3.49 (1H, s, H-5 GalNAc ), 3.45 (1H, s, H-4 Gal ), 2.94-2.86 (1H, m, CH2of Lev), 2.56-2.51 (3H, m, CH2of Lev, H-2 GlcNAc ), 2.31–2.28 (1H, m, CH2of Lev), 2.10 (3H, s, CH3CO), 2.04 (3H, s, CH3CO), 2.00 (12H, m, CH3CO); 13C NMR (150 MHz, CDCl3, TMS) δ 210.4, 172.3, 170.7, 169.9, 169.8, 169.4(2C), 166.9, 157.9 (q, J = 24.5 Hz, COCF3), 157.7 (q, J = 24.3). Hz, COCF3), 138.1, 137.9, 137.3, 137.2, 130.3, 128.6(2C); Hz, COCF3), 115.4 (q, J = 191.2 Hz, COCF3), 101.7; 71.9, 70.9, 70.1, 70.0, 69.9, 69.4, 69.3, 68.6, 66.5, 64.8, 62.3, 58.4, 52.6, 51.3, 37.9, 29.7, 27.7, 20.8, 20.6. 20.4; ESI-Q-TOF (positive mode) switchC72 H 84 F6N3O 29 + [M+NH4] + m / z 1568.5095, measured value 1568.5099.

[0095] Synthesis of methyl benzyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronate, (1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-α-D-galactopyranose, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Benzyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl ester (1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyranose-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (224 mg, 0.14 mmol) was dissolved in dichloromethane (2.0 mL). 0.5 M hydrazine acetate (0.87 mL, hydrazine hydrate dissolved in a 3:2 pyridine / acetic acid mixture) was added dropwise under ice bath conditions. The temperature was then allowed to rise slowly to room temperature and the reaction was continued for 1 hour. After detecting the completion of the reaction by TLC, the reaction solution was diluted with dichloromethane, and the organic phase was washed successively with 1M hydrochloric acid solution, saturated sodium bicarbonate solution, and saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH=50:1) to give a white solid (178 mg, 85%). f = 0.21 (DCM / MeOH 30:1); 1H NMR (600 MHz, CDCl3, TMS) δ 7.56, 7.39, 7.32-7.19, 7.01 (23H, m, aromatic, NH, OH), 5.61 (1H, s, PhCH), 5.14 (1H, t, H-4 GlcA , J = 9.4 Hz), 5.10 (1H, t, H-3 GlcA , J = 8.9 Hz), 5.06 (1H, d, H-1 Gal , J = 3.4 Hz), 4.90 (2H, m, H-2 GlcA , PhCH2), 4.81 (1H, d, H-1 GlcNAc , J = 8.4 Hz), 4.73 (2H, m, H-4 GlcNAc , PhCH2), 4.65-4.59 (3H, m, H-1 GalNAc , PhCH2), 4.41 (1H, d, H-1 GlcA , J = 8.0 Hz), 4.39-4.29 (5H, m, H-2 GalNAc , H-4 GalNAc , H-6a GalNAc , PhCH2), 4.26 (1H, dd, H-6a GlcNAc , J = 5.6 Hz, J = 12.6 Hz), 4.17 (2H, m, H-3 GlcNAc , H-6b GalNAc ), 4.06 (1H, m, H-6b GlcNAc ), 4.00 (1H, dd, H-2 Gal , J = 3.5 Hz, J = 10.2 Hz), 3.93 (2H, m, H-3 GalNAc , H-5 GlcA ), 3.76 (1H, dd, H-3 Gal , J = 2.6 Hz, J = 10.1 Hz), 3.72 (3H, s, OCH3), 3.70 (1H, m, H-5 Gal ), 3.61 (2H, m, H-6a Gal , H-5 GlcNAc ), 3.50 (1H, d, H-4 Gal , J = 1.4 Hz), 3.43 (2H, m, H-5GalNAc , H-2 GlcNAc ), 3.32 (1H, m, H-6b Gal ), 2.11 (3H, s, CH3CO), 2.00 (9H, m, CH3CO), 1.92 (3H, s, CH3CO); 13 C NMR (150 MHz, CDCl3, TMS) δ 171.2, 169.9, 169.6, 169.4, 169.3, 166.8, 157.8 (q, J = 24.5 Hz, COCF3), 157.5 (q, J = 24.6 Hz, COCF3), 138.0, 137.8, 137.7, 137.0, 129.4, 128.6, 128.4(2C), 128.2, 128.0(2C), 127.9(2C), 127.7, 126.3,115.8 (q, J = 191.1 Hz, COCF3), 115.5 (q, J = 191.1 Hz, COCF3), 101.0, 100.6, 100.2, 98.2, 97.5, 77.3, 76.7, 75.8, 74.7, 72.9, 72.4(2C), 72.3, 71.7, 70.9, 69.9, 69.3, 69.1, 68.1, 66.8, 62.5, 62.1, 56.7, 52.8, 52.7, 20.8, 20.6, 20.5, 20.4(2C); ESI-Q-TOF (positive mode) calculated value C 67 H 78 F6N3O 27 + [M+NH4] + m / z 1470.4727, measured value 1470.4736.

[0096] Synthesis of methyl benzyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid, (1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-α-D-pyrangalacturonic acid, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Benzyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl ester (1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose (1→2)-3,4-di-O-benzyl-α-D-galactopyranose (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (155 mg, 0.11 mmol) was dissolved in dichloromethane / water (0.8 mL / 0.4 mL). 2,2,6,6-tetramethylpiperidine-nitrogen-oxide (7 mg, 0.044 mmol, 0.4 equiv.) and diacetoxyiodobenzene (71 mg, 0.22 mmol, 2.0 equiv.) were added sequentially under ice bath conditions. The mixture was allowed to warm to room temperature and react overnight. After detecting the completion of the reaction by TLC, the reaction solution was diluted with dichloromethane, and the organic phase was washed with saturated sodium thiosulfate solution, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH=60:1, 0.1% CH3COOH) to give a pale yellow solid (135 mg, 86%). f = 0.18 (DCM / MeOH 30:1); 1 H NMR (600 MHz, CDCl3+CD3COOD, TMS) δ 7.58, 7.39, 7.31-7.24, 7.18, 7.15 (22H, m, aromatic, NH), 5.69 (1H, s, PhCH), 5.24 (1H, s, H-1 GalA ), 5.15 (2H, m, H-3 GlcA , H-4 GlcA ), 4.95 (1H, t, H-2 GlcA , J = 8.3 Hz), 4.91 (1H, d, PhCH2, J = 12.2 Hz), 4.78 (1H, t, H-4 GlcNAc , J = 9.5 Hz), 4.71-4.64 (5H, m, H-1 GlcNAc , H-1 GalNAc, 3PhCH2), 4.52 (1H, d, H-1 GlcA , J = 8.1 Hz), 4.46 (1H, s, H-4 GalNAc ), 4.36 (2H, m, H-6a GalNAc , PhCH2), 4.30-4.23 (5H, m, H-2 GalNAc , H-5 GalA , H-6a GlcNAc , H-6b GalNAc , PhCH2), 4.13 (1H, m, H-3 GlcNAc ), 4.05 (2H, m, H-3 GalNAc , H-6b GlcNAc ), 3.99 (2H, m, H-2 GalA , H-5 GlcA ), 3.86 (1H, dd, H-3 GalA , J = 2.2 Hz, J = 10.0 Hz), 3.80 (1H, s, H-4 GalA ), 3.73 (3H, s, OCH3), 3.71-3.60 (2H, m, H-2 GlcNAc , H-5 GlcNAc ), 3.47 (1H, s, H-5 GalNAc ), 2.13 (3H, s, CH3CO), 2.04 (3H, s, CH3CO), 2.00 (6H, s, 2CH3CO), 1.93 (3H, s, CH3CO); 13C NMR (150 MHz, CDCl3+CD3COOD, TMS) δ 172.8, 171.6, 170.3, 170.0, 169.9, 169.5, 167.2, 157.7 (q, J = 24.7 Hz, 2COCF3), 137.7, 137.0, 136.9, 129.5, 128.8, 128.5, 128.4, 128.2, 128.1(2C), 128.0, 127.8, 126.5, 115.8 (q, J = 191.1 Hz, 2COCF3), 101.4, 101.2, 100.5, 98.5, 77.7, 75.8, 75.6, 73.8, 72.5(3C), 71.0, 70.8, 70.1, 69.5, 69.1, 68.2, 66.7, 62.3, 56.1, 52.9, 52.5, 20.8, 20.6(2C), 20.4; ESI-Q-TOF (positive mode) calculated value C 67 H 76 F6N3O 28 + [M+NH4] + m / z 1484.4520, measured value 1484.4539.

[0097] Synthesis of methyl benzyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid, methyl (1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, methyl (1→2)-NL-threonine, methyl 3,4-di-O-benzyl-α-D-pyrangalacturonic acid, methyl (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Benzyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (70.0 mg, 0.048 mmol) was dissolved in anhydrous dichloromethane (0.6 mL). N-hydroxysuccinimide (11.0 mg, 0.096 mmol, 2.0 equiv.) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (18.4 mg, 0.096 mmol, 2.0 equiv.) were added sequentially, and the mixture was allowed to react at room temperature overnight. After detecting the completion of the reaction by TLC, the reaction mixture was diluted with dichloromethane, and the organic phase was washed successively with 1M hydrochloric acid solution, saturated sodium bicarbonate solution, and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting crude product was used directly in the next reaction. The crude product and L-threonine methyl ester (40.7 mg, 0.24 mmol, 5.0 equiv.) were dissolved in N,N-dimethylformamide / triethylamine (2.0 mL / 0.1 mL), heated to 40°C, and reacted overnight. After detecting the completion of the reaction by TLC, the reaction mixture was directly concentrated under reduced pressure and purified by column chromatography (DCM / MeOH=60:1) to obtain a pale yellow solid (59.6 mg, 79% yield for the two steps). f = 0.26 (DCM / MeOH 30:1); 1 H NMR (600 MHz, CDCl3, TMS) δ 8.00, 7.84, 7.54, 7.39, 7.33-7.17, 7.04 (23H, m, aromatic, NH), 5.68 (1H, s, PhCH), 5.23 (1H, d, H-1 GalA , J = 2.9 Hz), 5.15-5.10 (2H, m, H-3 GlcA , H-4 GlcA ), 4.92 (2H, m, H-2 GlcA , PhCH2), 4.79 (2H, m, H-1 GlcNAc , H-4GlcNAc ), 4.70 (1H, d, PhCH2, J = 10.9 Hz), 4.65 (2H, m, PhCH2, H-1 GalNAc ), 4.59 (1H, d, PhCH2, J = 12.3 Hz), 4.50 (1H, d, H-1 GlcA , J = 8.0 Hz), 4.48 (1H, d, H-4 GalNAc , J = 2.8 Hz), 4.45 (1H, dd, CH, J = 2.2 Hz, J = 8.9 Hz), 4.41 (1H, d, PhCH2, J = 11.0 Hz), 4.37 (2H, m, PhCH2, H-6a GalNAc ), 4.32-4.23 (6H, m, H-5 GalA , H-6a GlcNAc , H-2 GalNAc , H-6b GalNAc , H-3 GlcNAc , CH), 4.12 (2H, m, H-4 GalA , H-6b GlcNAc ), 4.02 (2H, m, H-2 GalA , H-3 GalNAc ), 3.94 (1H, m, H-5 GlcA ), 3.81 (1H, d, H-3 GalA , J = 2.2 Hz, J = 9.9 Hz), 3.71 (6H, s, 2OCH3), 3.62 (1H, m, H-5 GlcNAc ), 3.49 (1H, s, H-5 GalNAc ), 3.44 (1H, m, H-2 GlcNAc ), 2.12 (3H, s, CH3CO), 2.02 (3H, s, CH3CO), 1.99 (6H, s, 2CH3CO), 1.89 (3H, s, CH3CO), 0.96 (3H, d, CH3, J = 6.4 Hz); 13C NMR (150 MHz, CDCl3, TMS) δ 171.4(2C), 170.0, 169.7, 169.6, 169.4, 168.8, 167.0, 162.8, 157.8 (q, J = 24.6 Hz, 2COCF3), 157.5 (q, J = 24.6 Hz, 2COCF3), 138.4, 137.7, 137.5, 137.1, 129.4, 128.6, 128.5, 128.4, 128.1, 128.0, 127.9, 127.8, 127.7, 127.6, 126.3, 115.9 (q, J = 191.1 Hz, 2COCF3),115.7 (q, J = 191.1 Hz, 2COCF3), 101.0, 100.9, 100.2, 98.4, 97.7, 77.5, 76.5, 76.3, 76.2, 75.3, 75.1, 72.9, 72.6, 72.5, 72.4(2C), 72.1, 70.9, 70.1, 69.4, 69.0, 68.0, 67.4, 66.8, 62.1, 57.0, 56.6, 52.8, 52.7, 52.6, 20.7, 20.6, 20.5, 20.4(2C), 19.6; ESI-Q-TOF (positive mode) calculated value C 72 H 85 F6N4O 30 + [M+NH4] + m / z 1599.5153, measured value 1599.5133.

[0098] Synthesis of benzyl β-D-glucopyranosiduronic acid-(1→3)-2-deoxy-2-acetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-acetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Benzyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl ester-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (30.0 mg, 0.02 mmol) was dissolved in methanol (1.0 mL), and saturated lithium hydroxide solution (1.0 mL) was added dropwise. The mixture was heated to 35°C and reacted for 48 hours. After confirming the completion of the reaction by TLC, the reaction mixture was neutralized to pH 7 with IR-120 cation exchange resin, filtered, washed with methanol, and concentrated under reduced pressure. The resulting crude product was dissolved in a 1.0 mL / 1.0 mL mixture of methanol and water, and the pH was adjusted to 11-12 with solid potassium carbonate. Acetic anhydride (0.3 mL) was added dropwise, and the pH was adjusted to 11-12 with solid potassium carbonate. The mixture was allowed to react overnight at room temperature. After confirming the completion of the reaction by TLC, the reaction mixture was neutralized to pH 7 with IR-120 cation exchange resin, filtered, washed with methanol, and concentrated under reduced pressure. The filtrate was purified using Sephadex LH-20 with CHCl / MeOH 1:1 as an eluent to give a white solid (18.6 mg, 82% yield for two steps). f = 0.58 (CHCl3 / MeOH / H2O=1:1:0.3); 1 H NMR (600 MHz, MeOD-d6, TMS) δ 7.64, 7.40, 7.36-7.30, 7.27-7.19 (20H, m, aromatic), 5.61 (1H, s, PhCH), 5.41 (1H, s, H-1 GalA ), 4.89 (1H, m, PhCH2), 4.77 (3H, m, 2PhCH2, H-4 GalNAc ), 4.68-4.57 (5H, m, 3PhCH2, H-1 GlcNAc , H-1 GalNAc ), 4.29-4.19 (6H, m, H-4 GalA , H-5 GalA , H-1 GlcA , H-2GalNAc , H-6a GalNAc , H-6b GalNAc ), 4.03 (1H, d, H-2 GalA , J = 7.4 Hz), 3.93-3.81 (5H, m, H-3 GalA , H-2 GlcNAc , H-6a GlcNAc , H-6b GlcNAc , H-3 GalNAc ), 3.66 (1H, m, H-3 GlcNAc ), 3.59 (1H, m, H-5 GlcA ), 3.54 (1H, s, H-5 GalNAc ), 3.47 (2H, m, H-4 GlcA , H-4 GlcNAc ), 3.38 (1H, m, H-3 GlcA ), 3.35 (1H, s, H-5 GlcNAc ), 3.26 (1H, t, H-2 GlcA , J = 8.0 Hz); 13 C NMR (150 MHz, MeOD-d6, TMS) δ 175.9, 174.9, 174.1, 173.9, 140.2, 139.8, 139.1, 129.7, 129.4, 129.3, 129.1, 129.0, 128.9, 128.6, 128.4, 128.3, 127.8, 105.1, 104.8, 102.0, 101.2, 86.5, 80.7, 77.4, 77.3, 76.1, 75.4, 74.6, 74.2, 73.8, 73.3, 72.9, 71.5, 70.4, 70.1, 68.3, 62.3, 56.6, 52.3, 49.6, 23.3, 23.2; ESI-Q-TOF (negative mode) calculation value C 56 H 65 N2O 23 - [MH] - m / z 1133.3984, measured value 1133.3983.

[0099] Synthesis of β-D-glucopyranosiduronic acid-(1→3)-2-deoxy-2-acetylamino-β-D-glucupyranose-(1→2)-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-acetylamino-α,β-D-galactopyranose (compound CP-1) [ka] Benzyl β-D-glucopyranosiduronic acid-(1→3)-2-deoxy-2-acetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-acetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (18.6 mg, 16.4 μmol) was dissolved in a mixture of methanol and water (1.0 mL / 1.0 mL), and 10% palladium hydroxide on carbon (37.0 mg) was added. The mixture was reacted at room temperature for 48 hours under a hydrogen gas pressure of 40 Pa. After completion of the reaction was confirmed by TLC, the mixture was filtered, concentrated under reduced pressure, and purified using Sephadex LH-20 with purified water as the eluent to obtain a white solid (10.8 mg, 85%). f =0.11 (CHCl3 / MeOH / H2O=1:1:0.3); 1 H NMR (600 MHz, D2O) δ 5.31 (0.97H, s), 5.19 (0.53H, d, J = 3.3 Hz), 4.68 (1.69H, m), 4.49 (1.02H, d, J = 7.7 Hz), 4.37 (0.58H, s), 4.31 (0.49H, s), 4.24 (1.52H, m), 4.18 (0.63H, s), 4.11 (0.52H, m), 3.98-3.75 (11.26H, m), 3.70 (0.53H, m), 3.51 (3.46H, m), 3.35 (0.92H, m), 2.02 (3H, s), 1.98 (2.88H, d, J = 4.4 Hz); 13C NMR (150 MHz, D2O) δ 175.5, 103.9, 103.8, 103.7, 97.8, 97.5, 95.8, 92.0, 83.2, 78.7, 78.6, 78.4, 76.6, 76.2(3C), 76.0, 75.4, 73.5, 72.7, 72.4, 71.7, 70.7, 69.4(2C), 69.1, 69.0, 66.3, 65.4, 61.9, 61.7, 61.6, 61.5, 55.4, 52.8, 49.2, 23.0, 22.9, 22.7; ESI-Q-TOF (positive mode) calculated value C 28 H 42 N2O 23 2- [M-2H] 2- m / z 387.1095, measured 387.1090.

[0100] Synthesis of benzyl β-D-glucopyranosiduronic acid-(1→3)-2-deoxy-2-acetylamino-β-D-glucopyranose-(1→2)-NL-threonine-3,4-di-O-benzyl-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-acetylamino-β-D-galactopyranose [ka] Benzyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl ester (1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose (1→2)-NL-threonine methyl ester (1→3)-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (30 mg, 19.0 μmol) was dissolved in 80% aqueous AcOH (2.0 mL), heated to 60°C, and reacted for 2 hours. After the reaction was completed, the mixture was cooled to room temperature and the solvent was evaporated with toluene to obtain a crude product. The crude product was then directly dissolved in methanol (1.0 mL), saturated lithium hydroxide solution (1.0 mL) was added dropwise, and the mixture was heated to 35°C and reacted for 48 hours. After confirming the completion of the reaction by TLC, the reaction mixture was neutralized to pH = 7 with IR-120 cation exchange resin, filtered, washed with methanol, and concentrated under reduced pressure. The crude product obtained after concentration was dissolved in a mixture of methanol and water (1.0 mL / 1.0 mL), adjusted to pH = 11-12 with solid potassium carbonate, added dropwise with acetic anhydride (0.3 mL), and further adjusted to pH = 11-12 with solid potassium carbonate. The mixture was allowed to react overnight at room temperature. After confirming the completion of the reaction by TLC, the reaction mixture was neutralized to pH = 7 with IR-120 cation exchange resin, filtered, washed with methanol, and concentrated under reduced pressure. The residue was purified on Sephadex LH-20 using CHCl / MeOH 1:1 as an eluent to give a white solid (15.1 mg, 69% yield over three steps). 1 H NMR (600 MHz, CD3OD+D2O) δ 7.42-7.25 (15H, m, aromatic), 5.52 (1H, d, H-1 GalA , J = 3.7 Hz), 4.92-4.64 (6H, m, 5PhCH2, H-1 GlcNAc ), 4.49 (2H, m, H-1 GalNAc , PhCH2), 4.42 (1H, d, H-1 GlcA , J = 7.8 Hz), 4.37 (1H, d, H-4 GalNAc, J = 2.8 Hz), 4.32 (1H, m, H-4 GalA ), 4.29 (1H, s, H-5 GalA ), 4.21-4.16 (3H, m, CHOH, CHNH, H-2 GalNAc ), 4.12 (1H, dd, H-2 GalA , J = 3.6 Hz, J = 10.1 Hz), 3.98 (1H, dd, H-3 GalA , J = 2.9 Hz, J = 10.3 Hz), 3.94-3.77 (7H, m, H-6a GalNAc , H-6b GalNAc , H-3 GalNAc , H-2 GlcNAc , H-3 GlcNAc , H-6a GlcNAc , H-6b GlcNAc ), 3.68 (1H, d, H-5 GlcA , J = 9.6 Hz), 3.65 (1H, t, H-5 GalNAc , J = 6.7 Hz), 3.53-3.45 (4H, m, H-4 GlcA , H-4 GlcNAc , H-3 GlcA , H-5 GlcNAc ), 3.32 (1H, m, H-2 GlcA ), 1.84 (3H, s, CH3CO), 1.75 (3H, s, CH3CO), 0.98 (3H, d, CH3, J = 6.2 Hz); 13C NMR (150 MHz, CD3OD+D2O) δ 175.6, 173.7, 173.3, 169.2, 138.2, 137.8, 137.4, 128.4, 128.3, 128.1, 127.8, 127.7, 127.4, 103.3, 103.1, 100.9, 96.9, 83.2, 78.0, 77.9, 76.6, 76.1, 76.0, 75.7, 75.2, 74.8, 74.6, 73.0, 72.9, 71.9, 71.1, 70.8, 69.0, 67.7, 64.4, 60.9 (2C), 59.0, 55.0, 50.5, 22.0, 21.8, 19.1; ESI-Q-TOF (negative mode) calculated C 53 H 67 N3O 25 2- [M-2H] 2- m / z 572.7037, measured value 572.7036.

[0101] Example 2 Synthesis of β-D-glucopyranosiduronic acid-(1→3)-2-deoxy-2-acetylamino-β-D-glucupyranose-(1→2)-NL-threonine-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-acetylamino-α,β-D-galactopyranose (compound CP-2) [ka] Benzyl β-D-glucopyranosiduronic acid-(1→3)-2-deoxy-2-acetylamino-β-D-glucopyranose-(1→2)-NL-threonine-3,4-di-O-benzyl-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-acetylamino-β-D-galactopyranose (19.0 mg, 16.6 μmol) was dissolved in a mixture of methanol and water (1.0 mL / 1.0 mL), and 10% palladium hydroxide on carbon (38.0 mg) was added. The mixture was incubated at room temperature for 48 hours under a hydrogen gas pressure of 40 Pa. After completion of the reaction was confirmed by TLC, the mixture was filtered, concentrated under reduced pressure, and purified using Sephadex LH-20 eluent with purified water to obtain a white solid (12.5 mg, 86%). 1 H NMR (600 MHz, D2O) δ 5.46 (0.86H, m), 5.18 (0.48H, d, J = 3.6 Hz), 4.81 (0.56H, m), 4.66 (0.95H, m), 4.48 (0.98H, d, J = 7.9 Hz), 4.39 (0.47H, d, J = 2.4 Hz), 4.32-4.23 (5.18H, m), 4.14-4.06 (1.13H, m), 3.99-3.68 (11.95H, m), 3.55-3.47 (4.46H, m), 3.34 (1.26H, m); 13 C NMR (150 MHz, D2O) δ 175.69, 175.03, 170.93, 170.76, 103.9, 103.8, 103.7, 98.0, 97.7, 96.0, 92.0, 83.1, 79.0, 78.3, 78.2, 76.6, 76.4, 76.2(2C), 76.0, 75.4, 73.5, 72.5, 72.2, 72.1, 70.7, 70.6(2C), 69.4, 69.3, 69.1, 69.0, 68.7(2C), 66.4, 65.5, 61.9, 61.6, 61.5, 60.4, 55.4, 52.6, 49.2, 23.0, 22.8, 22.5, 20.0; ESI-Q-TOF (negative mode) calculated value C 32 H 49 N3O 252- [M-2H] 2- m / z 437.6333, observed value 437.6323.

[0102] Example 3 Synthesis of methyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-β-D-galactopyranose [ka] Under argon gas protection, p-tolyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-1-thio-β-D-galactopyranose (101 mg, 0.20 mmol), N-iodosuccinimide (70 mg, 0.31 mmol, 1.5 equiv.), and 4 Å molecular sieves were dissolved in anhydrous dichloromethane (1.7 mL), and methanol (50 μL, 1.24 mmol, 6.0 equiv.) was added. The mixture was stirred at room temperature for 2 hours, then the temperature was lowered to -20°C, and trifluoromethanesulfonic acid (5.0 μL, 62.5 μmol, 0.30 equiv.) was added dropwise. The mixture was stirred for 3 hours, then the mixture was transferred to room temperature, and the mixture was allowed to react overnight. After the completion of the reaction was detected by TLC, it was quenched by adding an appropriate amount of triethylamine, filtered through molecular sieves with diatomaceous earth, the cake was washed several times with dichloromethane, the filtrates were combined, concentrated under reduced pressure and purified by column chromatography (petroleum ether / EtOAc 3:1) to give a white solid (73 mg, 88%). f = 0.39 (petroleum ether / EtOAc 1:1); 1 H NMR (400 MHz, CCl3, TMS) δ 7.29 (1H, d, J = 8.9 Hz, NH), 5.37 (1H, d, J=3.2 Hz), 5.28 (1H, dd, J = 11.2, 3.4 Hz), 4.57 (1H, d, J = 8.4 Hz) 4.25-4.06 (3H, m), 3.98 (1H, t, J = 6.5), 3.49 (3H, s), 2.15 (3H, s), 2.03 (3H, s), 1.96 (3H, s); 13C NMR (100 MHz, CDCl3, TMS) δ 170.5, 170.5, 170.2, 157.5, 114.2, 101.2, 70.7, 69.5, 66.5, 61.3, 57.0, 51.8, 20.6, 20.6, 20.3. MS (ESI-MS) Calculated value C 15 H 21 F3NO9 + [M+H] + m / z 415.3, observed value 416.3.

[0103] Synthesis of methyl 2-deoxy-2-trifluoroacetylamino-β-D-galactopyranose [ka] Methyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-β-D-galactopyranose (3.10 g, 7.48 mmol) was dissolved in methanol (50.0 mL), and an appropriate amount of sodium methanol was added to adjust the pH to 9-10. The reaction was allowed to proceed with stirring at room temperature for 2 hours. After the completion of the reaction was detected by TLC, the reaction solution was neutralized to pH 7 by adding cationic resin, filtered, and the filtrate was concentrated under reduced pressure to dryness, yielding a yellow syrup. f =0.75 (DCM / MeOH 5:1) and used directly in the next reaction.

[0104] Synthesis of methyl 2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, methyl 2-deoxy-2-trifluoroacetylamino-β-D-galactopyranose (2.16 g, 7.48 mmol) and (+)-camphorsulfonic acid (3.46 g, 14.9 mmol, 2.0 equiv.) were dissolved in anhydrous acetonitrile (60.0 mL), and benzaldehyde dimethyl acetal (4.36 mL, 29.0 mmol, 4.0 equiv.) was added. The temperature was raised to 40 °C and the reaction was carried out overnight. After the reaction was confirmed to be complete by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The reaction solution was concentrated under reduced pressure and purified by column chromatography (petroleum ether / EtOAc 2:1) to obtain the compound as a white solid (2.24 g, 80%). f = 0.72 (petroleum ether / acetone 1:2). MS (ESI-MS) calculated value C 16 H 19 F3NO6 + [M+H] + m / z 378.3, observed value 378.3.

[0105] Methyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, p-tolyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-1-thio-β-D-galactopyranose (5.80 g, 8.48 mmol, 1.5 equiv.) and methyl 2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (2.15 g, 5.70 mmol) were dissolved in anhydrous dichloromethane / N,N-dichloromethane. The mixture was dissolved in methylformamide (70.0 mL / 14.0 mL), 4Å molecular sieves (8.0 g) were added, and the mixture was stirred at room temperature for 2 hours. After cooling to 0 ° C, N-iodosuccinimide (2.50 g, 11.1 mmol, 2.0 equiv.) and silver trifluoromethanesulfonate (731 mg, 2.85 mmol, 0.5 equiv.) were added sequentially. The mixture was stirred at 0 ° C for 2 hours, then the temperature was gradually raised to room temperature and the mixture was allowed to react overnight. After detecting the completion of the reaction by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The molecular sieves were removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure and purified by column chromatography (petroleum ether / EtOAc 1:1) to obtain compound I-12 (4.66 g, 87%) as a white solid. f = 0.58 (DCM / MeOH 25:1); 1H NMR (400 MHz, CDCl3, TMS) δ 7.75 (1H, b), 7.61-7.48 (2H, m), 7.39-7.17 (13H, m), 6.95 (2H, d, J = 8.5 Hz), 6.62 (2H, d, J = 8.6 Hz), 5.54 (1H, s,), 5.20 (1H, d, J = 3.6 Hz), 4.94 (1H, d, J = 11.4 Hz), 4.85-4.73 (2H, m), 4.65 (1H, d, J = 11.8 Hz), 4.54 (1H, d, J = 11.4 Hz), 4.46 (2H, s), 4.42 (1H, s), 4.32 (1H, d, J = 12.4), 4.20 (3H, q, J = 5.3, 4.0 Hz), 4.12-4.02 (4H, m), 3.92-3.87 (1H, m), 3.85-3.81 (1H, m), 3.79-3.74 (1H, m), 3.73(3H, s) 3.50 (3H, s), 2.90-2.79 (1H, m), 2.75-2.38 (3H, m), 2.18 (3H, s); 13 C NMR (100 MHz, CDCl3, TMS) δ 208.9, 172.5, 158.9, 157.2 (COCF3), 138.6, 138.3, 137.6, 130.5, 129.5, 129.0, 128.4, 128.3(2C), 128.2, 127.8, 127.7, 127.5, 126.4, 116.0 (COCF3), 113.5, 101.1, 100.6, 92.8, 78.2, 75.4, 74.7, 74.6, 73.5, 71.4, 71.1, 70.5, 70.1, 69.4, 66.5, 64.2, 56.5, 55.2, 52.5, 38.0, 29.8, 27.8; ESI-Q-TOF (positive mode) calculated value C 49 H 54 F3NO 14 + [M+NH4] + m / z 955.3840, measured value 955.3956.

[0106] Methyl 3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Methyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-β-D-galactopyranose-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (4.66 g, 4.97 mmol) was dissolved in dichloromethane / water (100 mL / 10.0 mL), and 2,3-dichloro-5,6-dicyano-p-benzoquinone (2.17 g, 9.56 mmol, 1.9 equiv.) was added in batches. The mixture was allowed to react at room temperature for 1 hour. After the completion of the reaction was detected by TLC, the reaction solution was diluted with dichloromethane, and the organic phase was washed successively with saturated sodium bicarbonate solution, saturated sodium thiosulfate solution, and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH 40:1) to give a white solid (3.32 mg, 82%). f = 0.79 (petroleum ether / acetone 1:1); 1H NMR (400 MHz, CDCl3, TMS) δ 7.71 (1H, d, J = 9.3 Hz), 7.55 (2H, dd, J = 7.8, 1.8 Hz), 7.43–7.22 (13H, m), 5.60 (1H, s), 5.19 (1H, d, J = 3.9 Hz), 4.94 (1H, d, J = 11.4 Hz), 4.86 (1H, d, J = 11.8 Hz), 4.67-4.57 (2H, m), 4.50 (1H, d, J = 11.5 Hz), 4.47-4.35 (3H, m), 4.20 (1H, dd, J = 11.8,000). 2.7 Hz), 4.15–4.02 (4H, m), 3.83–3.76 (1H, m), 3.72 (1H, b), 3.58 (1H, dd, J = 10.0, 2.7 Hz), 3.52–3.46 (4H, m), 2.93 (1H, ddd, J = 19.1,000). 10.1, 3.5 Hz), 2.74–2.55 (2H,m), 2.42(1H,m), 2.21(3H,s); 13 C NMR (100 MHz, CDCl3, TMS) δ 210.3, 172.2, 157.3(COCF3), 138.5, 138.2, 137.2, 129.1, 128.4, 128.3, 128.3(2C), 127.8(2C), 126.2, 115.9(COCF3), 101.0(2C), 94.5, 79.6, 75.5, 74.6, 74.0, 73.0, 70.6, 70.3, 69.2, 69.1, 66.5, 64.7, 56.3, 50.8, 30.0, 27.7. ESI-Q-TOF (positive mode) switchC 41 H 50 F3NO 13 + [M+NH4] + m / z 835.3840;

[0107] Synthesis of methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid, methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyranose, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetamino-D-glucopyranose[2,1,-d]2-oxazoline (1.50 g, 2.28 mmol, 1.4 equiv.) and methyl 3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetamino) were mixed. Oroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (1.35 g, 1.65 mmol) was dissolved in anhydrous dichloromethane (30.0 mL), 4 Å molecular sieves (3.00 g) were added, and the mixture was stirred at room temperature for 2 hours. After that, the mixture was cooled to -20 °C. Trifluoromethanesulfonic acid trimethylsilylate (81 μL, 0.47 mmol, 0.3 equiv.) was added, and the mixture was stirred at -20 °C for 2 hours. The temperature was then gradually raised to room temperature and allowed to react overnight. After detecting the completion of the reaction by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The molecular sieves were removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure and purified by column chromatography (petroleum ether / acetone 2:1) to give a white solid (2.11 g, 87%). f = 0.43 (petroleum ether / acetone 1:1); 1H NMR (400 MHz, CDCl3, TMS) δ 8.47 (1H, d, J = 6.6 Hz), 7.98 (1H, d, J = 9.4 Hz), 7.66-7.55 (2H, m), 7.51-7.39 (3H, m), 7.38-7.23 (8H, m), 7.19-7.06 (2H, m), 5.60 (1H, s), 5.16 (1H, t, J = 9.6 Hz), 5.12-5.03 (2H, m), 5.01-4.91 (2H, m), 4.79 (1H, d, J = 11.6 Hz), 4.72-4.60 (3H, m), 4.58 (1H, d, J = 8.5 Hz), 4.48-4.33 (5H, m), 4.27 (2H, dd, J = 11.9, 6.4 Hz), 4.20 (1H, dd, J = 11.9, 2.1 Hz), 4.17-4.06 (2H, m), 3.95 (1H, d, J = 9.9 Hz), 3.92-3.86 (2H, m), 3.83 (1H, dd, J = 8.1, 3.8 Hz), 3.71 (3H, s), 3.67 (1H, d, J = 2.7 Hz), 3.65-3.56 (2H, m), 3.51 (3H, s), 3.48 (2H, b), 3.01 (1H, ddd, J = 19.0, 11.2, 3.3 Hz), 2.62-2.55 (2H, m), 2.46 (1H, q, J = 8.6, 8.1 Hz), 2.33 (1H, ddd, J = 17.0, 5.5, 3.3 Hz), 2.22 (3H, s), 2.10 (3H, s), 2.02 (3H, s), 2.02 (3H, s), 2.00 (6H, s); 13C NMR (100 MHz, CDCl3, TMS) δ 210.9, 172.4, 170.8, 169.9(2C), 169.5, 169.4, 167.0, 157.9 (COCF3), 157.8 (COCF3), 138.1, 137.9, 137.1, 130.5, 128.7, 128.6, 128.3, 128.2, 128.0, 127.8, 127.8, 126.4, 117.4 (COCF3), 115.4 (COCF3), 101.8, 100.9, 100.3, 98.5, 93.5, 77.8, 76.2, 75.8, 74.8, 73.7, 73.5, 72.7, 72.4, 71.9, 70.9, 70.0, 69.8, 69.4, 69.3, 68.7, 66.5, 64.9, 62.4, 58.5, 56.3, 52.6, 51.0, 38.0, 29.9, 27.7, 20.6 (2C), 20.4 (2C); ESI-Q-TOF (positive mode) calculated C 66 H 76 F6N2O 29 + [M+NH4] + m / z 1492.4782, observed value 1492.4733.

[0108] Synthesis of methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid, methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-α-D-galactopyranose, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid, methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyranose-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (1.51 g, 1.02 mmol) was dissolved in dichloromethane / methanol (10 mL / 2 mL). Hydrazine acetate (182 mg, 2.02 mmol, 2 equiv.) was added under ice bath conditions, and the mixture was allowed to warm to room temperature overnight. After detecting the completion of the reaction by TLC, the reaction solution was diluted with dichloromethane, and the organic phase was washed successively with 1M hydrochloric acid solution, saturated sodium bicarbonate solution, and saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH=50:1) to give a white solid (1.20 g, 86%). f = 0.46 (DCM / MeOH 20:1); 1H NMR (400 MHz, CDCl3, TMS) δ 8.59 (1H, b), 8.16 (1H, d, J = 9.7 Hz), 7.58-7.49 (2H, m), 7.45-7.37 (3H, m), 7.35-7.22 (9H, m), 7.19-7.11 (2H, m), 5.50 (1H, s), 5.21-4.99 (3H, m), 4.97-4.86 (2H, m), 4.77 (1H, d, J = 11.1 Hz), 4.66 (1H, d, J = 12.1 Hz), 4.59-4.46 (2H, m), 4.45-4.25 (5H, m), 4.26-4.14 (2H, m), 4.11 (1H, s), 4.05 (1H, dd, J = 10.1, 3.2 Hz), 3.94 (1H, d, J = 9.7 Hz), 3.92-3.82 (3H,m), 3.78-3.66 (6H,m), 3.56 (2H, s), 3.52-3.46 (5H, m), 3.24 (1H, s), 2.08 (3H, s), 2.04 (3H, s), 1.99 (6H, s), 1.93 (3H, s); 13 C NMR (100 MHz, CDCl3, TMS) δ 171.1, 169.9, 169.8, 169.7, 169.4, 167.0, 158.1 (COCF3), 157.8 (COCF3) 138.0, 137.9, 137.4, 130.0, 128.7, 128.6, 128.4, 128.0, 128.0, 126.2, 117.0 (COCF3), 114.3 (COCF3), 100.9, 100.7, 100.3(2C), 99.5, 77.9, 74.8, 73.5, 72.5, 72.0, 70.8, 69.4, 68.5, 66.3, 62.4, 57.7, 56.6, 52.7, 20.8, 20.6, 20.5, 20.4, 20.2.

[0109] Synthesis of methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid, methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-α-D-pyrangalacturonic acid, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronate, methyl(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-α-D-galactopyranose-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (950 mg, 0.69 mmol) was dissolved in dichloromethane / water (16.0 mL / 8.0 mL). 2,2,6,6-tetramethylpiperidine-nitrogen-oxide (44 mg, 0.28 mmol, 0.4 equiv.) and diacetoxyiodobenzene (440 mg, 1.36 mmol, 2.0 equiv.) were added sequentially under ice bath conditions. The mixture was allowed to warm to room temperature and react overnight. After detecting the completion of the reaction by TLC, the reaction solution was diluted with dichloromethane, and the organic phase was washed with saturated sodium thiosulfate solution, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH=50:1) to give a pale yellow solid (902 mg, 94%). f = 0.18 (DCM / MeOH 30:1); 11H NMR (400 MHz, DMSO-d6, TMS) δ 7.56 (2H, d, J = 7.4 Hz), 7.48 - 7.09 (15H, m), 5.72 (1H, s), 5.29 (1H, s), 5.19 (1H, t, J = 9.3 Hz), 4.92 (1H, t, J = 9.7 Hz), 4.82 - 4.61 (6H, m), 4.61 - 4.43 (3H, m), 4.41 - 4.29 (4H, m), 4.20 (1H, d, J = 12.1 Hz), 4.16 - 4.07 (3H, m), 4.00 (2H, d, J = 11.7 Hz), 3.90 (5H, s), 3.80 - 3.70 (1H, m), 3.66 (3H, s), 3.58 (1H, s), 3.38 (3H, s), 2.13 - 1.92 (12H, m), 1.88 (3H, s); 13 13C NMR (100 MHz, DMSO-d6, TMS) δ 170.6, 169.9, 169.8, 169.7, 169.6, 167.6, 156.9(COCF3), 156.6(COCF3) 139.0, 138.7, 138.6, 129.0, 128.7, 128.5, 128.4, 128.1, 128.0, 127.9, 126.4, 117.6 (COCF3), 114.8 (COCF3), 101.7, 101.1 (2C), 100.0, 75.6, 75.4, 73.1, 72.0, 71.8, 71.3, 70.6, 69.8, 69.0, 66.5, 62.4, 56.5, 53.1, 21.1, 20.9, 20.7, 20.6, 20.4; ESI-Q-TOF (positive mode) calculated value C 61 H 68 F6N2O …… 28 + [M + NH4] + m / z 1408.4207, measured value 1408.4362.

[0110] Synthesis of methyl β-D-glucopyranosiduronic acid, (1→3)-2-deoxy-2-acetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-α-D-pyrangalacturonic acid, (1→3)-2-deoxy-2-acetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid, methyl(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-α-D-pyrangalacturonic acid, (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (468 mg, 0.34 mmol) was dissolved in methanol (8.0 mL), and saturated lithium hydroxide solution (8.0 mL) was added dropwise. The mixture was heated to 35°C and reacted for 48 hours. After confirming the completion of the reaction by TLC, the reaction mixture was neutralized to pH 7 with IR-120 cation exchange resin, filtered, washed with methanol, and the filtrate was concentrated under reduced pressure. The crude product obtained after concentration was dissolved in a mixture of methanol and water (8.0 mL / 8.0 mL), and solid potassium carbonate was added to adjust the pH to 11-12. Acetic anhydride (2.4 mL) was added dropwise, and further solid potassium carbonate was added to adjust the pH to 11-12. The reaction was allowed to proceed overnight at room temperature. After confirming the completion of the reaction by TLC, the reaction mixture was neutralized to pH 7 with IR-120 cation exchange resin, filtered, washed with methanol, and the filtrate was concentrated under reduced pressure. The product was purified using Sephadex LH-20 with CHCl / MeOH 1:1 as an eluent to obtain a white solid (containing salts, which was directly used in the next step). f = 0.70 (CHCl3 / MeOH / H2O / acetone = 4:3:1:2); 1H NMR (600 MHz, CD3OD, TMS) δ 7.67 (2H, d, J = 7.7 Hz), 7.47 (2H, t, J = 7.6 Hz), 7.40 (1H, t, J = 7.5 Hz), 7.36-7.16 (10H, m), 5.84 (1H, s), 5.48 (1H, b), 4.78-4.75 (1H, m), 4.73-4.68 (1H, m), 4.69-4.60 (2H, m), 4.56 (1H, d, J = 12.1 Hz), 4.53-4.44 (2H, m), 4.44-4.34 (2H, m), 4.24 (2H, s), 4.10-4.00 (3H, m), 3.96-3.82 (2H, m), 3.72-3.65 (3H, m), 3.64-3.55 (3H, m), 3.53-3.40 (4H, m), 3.31 (4H, s), 1.95 (3H, s), 1.64 (3H, s); 13 C NMR (100 MHz, CD3OD, TMS) δ 172.9, 172.8 (2C), 138.6, 137.7, 129.4, 128.7, 128.1, 127.8, 127.7, 127.2, 127.1, 126.9, 126.3, 104.4, 103.7, 101.8, 101.1, 77.3, 76.6, 76.2, 75.4, 74.8, 74.2, 73.5, 72.0 (2C), 71.5, 69.0, 68.9, 66.6, 55.8, 54.5, 50.1, 22.8, 21.8; ESI-Q-TOF (positive mode) calculated value C 50 H 62 N2O 23 + [M+NH4] + m / z 1076.4087, observed value 1076.4073.

[0111] Synthesis of methyl β-D-glucopyranosiduronic acid-(1→3)-2-deoxy-2-acetylamino-β-D-glucopyranose-(1→2)-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-acetylamino-α,β-D-galactopyranose [ka] Benzyl β-D-glucopyranosiduronic acid-(1→3)-2-deoxy-2-acetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-acetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (all 0.34 mmol in the previous step) was dissolved in a mixture of methanol and water (5.0 mL / 5.0 mL), and 20% palladium hydroxide on carbon (480 mg) was added. The mixture was incubated at room temperature for 48 hours under hydrogen gas pressure of 40 Pa. After completion of the reaction was confirmed by TLC, the mixture was filtered, concentrated under reduced pressure, and purified using Sephadex LH-20 with purified water as the eluent to give a white solid (95 mg, 52% yield in two steps). Rf =0.11 (CHCl3 / MeOH / H2O =1:1:0.3); 1 H NMR (400 MHz, D2O) δ 5.29 (1H, s), 4.64 (1H, d, J = 8.5 Hz), 4.48 (1H, d, J = 8.0 Hz), 4.41 (1H, d, J = 8.7 Hz), 4.34-4.11 (3H, m), 3.98-3.69 (11H, m), 3.69-3.60 (1H, m), 3.60-3.42 (7H, m), 3.39-3.22 (1H, m), 1.98 (3H, s), 1.94 (3H, s); 13 C NMR (100 MHz, D2O) δ 176.2, 103.1, 103.0, 102.2, 96.7, 82.6, 77.8, 75.5, 75.3, 74.7, 72.8, 72.0, 71.7, 71.1, 68.7, 68.4, 64.7, 61.0, 60.8, 57.0, 54.7, 50.7, 22.3, 22.1; ESI-Q-TOF (negative mode) calculated value C 29 H 46 N2O 23 - [MH + ] -m / z 789.2413, observed value 789.2446.

[0112] Example 4 Synthesis of ethyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-β-D-galactopyranose [ka] Under argon gas protection, p-tolyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-1-thio-β-D-galactopyranose (2.0 g, 3.94 mmol), N-iodosuccinimide (1.24 g, 5.51 mmol, 1.4 equiv.), and 4 Å molecular sieves were dissolved in anhydrous dichloromethane (30 mL), and ethanol (0.69 mL, 11.8 mmol, 3.0 equiv.) was added. The mixture was stirred at room temperature for 2 hours, then cooled to -30°C, and trimethyl trifluoromethanesulfonate (0.27 mL, 1.55 mmol, 0.40 equiv.) was added dropwise. The mixture was stirred for 3 hours, then transferred to room temperature, and allowed to react overnight. After the completion of the reaction was detected by TLC, it was quenched by adding an appropriate amount of triethylamine, filtered through molecular sieves with diatomaceous earth, the cake was washed several times with dichloromethane, the filtrates were combined, concentrated under reduced pressure and purified by column chromatography (petroleum ether / EtOAc 3:1) to give a white solid (1.51 g, 89%). f = 0.45 (petroleum ether / EtOAc 1:1); 1 H NMR (400 MHz, CDCl3, TMS) δ 7.21 (1H, d, J = 9.0 Hz), 5.37 (1H, d, J = 3.4), 5.33 - 5.18 (2H, m), 4.66 (1H, d, J = 8.3 Hz,), 4.23-4.07 (2H, m), 4.00-3.94 (1H, m), 3.94-3.86 (1H, m), 3.62-3.52 (1H, m), 2.14 (3H, s), 2.03 (3H, s), 1.97 (3H, s), 1.18 (3H, t, J = 7.1 Hz); 13C NMR (100 MHz, CDCl3, TMS) δ 170.7, 170.6, 170.3, 157.8 (COCF3), 115.7 (COCF3), 100.2, 70.7, 69.6, 66.7, 65.6, 61.6, 51.8, 20.6, 20.6, 20.4, 14.8.

[0113] Synthesis of ethyl 2-deoxy-2-trifluoroacetylamino-β-D-galactopyranose [ka] Ethyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-β-D-galactopyranose (1.51 g, 3.52 mmol) was dissolved in methanol (50.0 mL), and an appropriate amount of sodium methanol was added to adjust the pH to 9-10. The reaction was allowed to proceed with stirring at room temperature for 2 hours. After the completion of the reaction was detected by TLC, the reaction solution was neutralized to pH 7 by adding cationic resin, filtered, and the filtrate was concentrated under reduced pressure to dryness, yielding a yellow syrup. f =0.57 (DCM / MeOH 5:1) and used directly in the next reaction.

[0114] Synthesis of ethyl 2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, ethyl 2-deoxy-2-trifluoroacetylamino-β-D-galactopyranose (1.07 g, 3.52 mmol) and (+)-camphorsulfonic acid (1.90 g, 8.18 mmol, 2.3 equiv.) were dissolved in anhydrous acetonitrile (30.0 mL), and benzaldehyde dimethyl acetal (2.50 mL, 16.6 mmol, 4.6 equiv.) was added. The temperature was raised to 40 °C and the reaction was carried out overnight. After the reaction was confirmed to be complete by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The reaction solution was concentrated under reduced pressure and purified by column chromatography (petroleum ether / EtOAc = 2:1) to obtain the compound as a white solid (1.01 g, 74%). f =0.68 (petroleum ether / acetone = 1:2).

[0115] Ethyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, p-tolyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-1-thio-β-D-galactopyranose (2.21 g, 3.23 mmol, 1.4 equiv.) and ethyl 2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (0.90 g, 2.30 mmol) were dissolved in anhydrous dichloromethane / N,N-dichloromethane. Dissolved in methylformamide (30.0 mL / 6.0 mL), 4Å molecular sieves (3.6 g) were added, and the mixture was stirred at room temperature for 2 hours. After cooling to 0 ° C, N-iodosuccinimide (0.90 g, 4.00 mmol, 1.7 equiv.) and silver trifluoromethanesulfonate (193 mg, 0.75 mmol, 0.3 equiv.) were added sequentially. The mixture was stirred at 0 ° C for 2 hours, then allowed to warm to room temperature and react overnight. After detecting the completion of the reaction by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The molecular sieves were removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure and purified by column chromatography (petroleum ether / EtOAc 1:1) to obtain compound I-12 (1.96 g, 89%) as a white solid. f = 0.74 (DCM / MeOH 20:1); 11H NMR (400 MHz, CDCl3, TMS) δ 7.58 - 7.47 (3H, m), 7.28 (13H, m), 6.92 (2H, d, J = 8.6 Hz), 6.62 (2H, d, J = 8.6 Hz), 5.53 (1H, s), 5.23 (1H, d, J = 3.5 Hz), 4.96 (1H, d, J = 11.5 Hz), 4.84 - 4.76 (2H, m), 4.65 (1H, d, J = 11.7 Hz), 4.54 (1H, d, J = 11.5 Hz), 4.48 - 4.38 (3H, m), 4.36 - 4.27 (2H, m), 4.22 (1H, dd, J = 11.7, 3.2 Hz), 4.15 (1H, dd, J = 10.9, 3.4 Hz), 4.11 - 4.00 (3H, m), 3.94 (1H, dd, J = 9.7, 7.1 Hz), 3.87 (1H, dd, J = 10.0, 2.7 Hz), 3.85 - 3.80 (1H, b), 3.79 - 3.71 (4H, m), 3.61 - 3.51 (1H, m), 3.46 (1H, s), 2.94 - 2.82 (1H, m), 2.72 - 2.51 (2H, m), 2.46 - 2.37 (1H, m), 2.17 (3H, s), 1.17 (3H, t, J = 7.0 Hz); 13 13C NMR (100 MHz, CDCl3, TMS) δ 209.2, 172.5, 158.9, 157.2 (COCF3), 138.7, 138.3, 137.6, 130.6, 129.3, 129.1, 128.4, 128.3 (2C), 128.2, 127.8, 127.7, 127.5, 126.5, 116.0 (COCF3), 113.5, 101.2, 99.6, 92.7, 78.2, 75.6, 74.9, 74.6, 73.7, 71.5, 71.3, 70.5, 70.2, 69.5, 66.5, 64.8, 64.6, 55.3, 52.4, 3, 29.8, 27.8, 15.0; ESI-Q-TOF (positive mode) calculated value C 50 H 56F3NO 14 + [M+NH4] + m / z 969.3997, measured value 969.4011.

[0116] Ethyl 3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Ethyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-β-D-galactopyranose-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (140 mg, 0.15 mmol) was dissolved in dichloromethane / water (2.90 mL / 0.29 mL), and 2,3-dichloro-5,6-dicyano-p-benzoquinone (44 mg, 0.22 mmol, 1.5 equiv.) was added in batches. The mixture was allowed to react at room temperature for 1 hour. After completion of the reaction was confirmed by TLC, the reaction mixture was diluted with dichloromethane, and the organic phase was washed successively with saturated sodium bicarbonate solution, saturated sodium thiosulfate solution, and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH 40:1) to give a white solid (88 mg, 72%). R f = 0.69 (petroleum ether / acetone 1:1); 1H NMR (400 MHz, CDCl3, TMS) δ 7.67 (1H, d, J = 9.4 Hz), 7.58-7.50 (2H, m), 7.44-7.21 (13H, m), 5.58 (1H, s), 5.18 (1H, d, J = 3.9 Hz), 4.93 (1H, d, J = 11.4 Hz), 4.86 (1H, d, J = 11.8 Hz), 4.69-4.58 (2H, m), 4.50 (1H, d, J = 11.4 Hz), 4.48-4.31 (3H, m), 4.19 (1H, dd, J = 11.8, 2.9 Hz), 4.17-4.00 (4H, m), 3.92 (1H, dd, J = 9.7, 7.0 Hz), 3.83-3.77 (1H, m), 3.75-3.70 (1H, m), 3.59 (1H, dd, J = 10.0, 2.8 Hz), 3.53 (1H, dd, J = 9.7, 7.0 Hz), 3.44 (1H, s), 2.96-2.85 (1H, m), 2.76-2.35 (3H, m), 2.20 (3H, s), 1.17 (3H, t, J = 7.0 Hz); 13 C NMR (100 MHz, CDCl3, TMS) δ 210.2, 172.2, 157.3(COCF3), 138.5, 138.2, 137.3, 129.0, 128.4, 128.3 (2C), 127.8, 127.6, 126.2, 115.9 (COCF3), 100.9, 100.0, 94.5, 79.7, 75.4, 74.6, 73.9, 73.1, 70.6, 70.4, 69.3, 69.1, 66.4, 64.7, 64.6, 51.1, 38.1, 29.9, 27.7, 15.0.

[0117] Synthesis of ethyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid, methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyranose, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetamino-D-glucopyranose[2,1,-d]2-oxazoline (400 mg, 0.61 mmol, 1.4 equiv.) and ethyl 3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetamino) were mixed. Oroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (360 mg, 0.43 mmol) was dissolved in anhydrous dichloromethane (8.0 mL), 4 Å molecular sieves (800 mg) were added, and the mixture was stirred at room temperature for 2 hours, then cooled to -20 °C. Trifluoromethanesulfonic acid trimethylsilylate (21.6 μL, 0.13 mmol, 0.3 equiv.) was added, and the mixture was stirred at -20 °C for 2 hours, then allowed to warm slowly to room temperature and react overnight. After detecting the completion of the reaction by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The molecular sieves were removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure and purified by column chromatography (petroleum ether / acetone 2:1) to give a white solid (664 mg, 94%). f = 0.45 (petroleum ether / acetone 1:1); 1H NMR (400 MHz, CDCl3, TMS) δ 8.52 (1H, d, J = 6.6 Hz), 8.00 (1H, d, J = 9.3 Hz), 7.67-7.50 (2H, m), 7.53-7.39 (3H, m), 7.39-7.21 (8H, m), 7.14 (2H, dd, J = 7.7, 1.8 Hz), 5.59 (1H, s), 5.16 (1H, t, J = 9.6 Hz), 5.11-5.02 (2H, m), 5.00-4.93 (2H, m), 4.79 (1H, d, J = 11.6 Hz), 4.74-4.57 (4H, m), 4.44 (1H, d, J = 3.6 Hz), 4.43-4.36 (3H, m), 4.34 (1H, d, J = 12.0 Hz), 4.27 (2H, dd, J = 11.8, 6.1 Hz), 4.20 (1H, d, J = 11.9), 4.16-4.08 (2H, m), 3.99-3.92 (2H, m), 3.89 (2H, dt, J = 12.3, 2.7 Hz), 3.81 (1H, dd, J = 11.8, 8.5 Hz), 3.71 (3H, s), 3.68 (1H, d, J = 2.8 Hz), 3.65-3.56 (2H, m), 3.53 (1H, dd, J = 9.6, 7.1 Hz), 3.46 (2H, b), 3.07-2.95 (1H, m), 2.69-2.55 (2H, m),2.46 (1H, dd, J = 17.2, 8.5 Hz), 2.33 (1H, dt, J = 16.9, 4.1 Hz), 2.21 (3H, s), 2.10 (3H, s), 2.02 (3H, s), 2.01 (3H, s), 1.99 (6H, s), 1.20 (3H, t, J = 7.0 Hz); 13C NMR (100 MHz, CDCl3, TMS) δ 210.8, 172.4, 170.7, 169.9 (2C), 169.5, 169.4, 167.0, 157.9 (COCF3), 157.6 (COCF3), 138.1, 137.9, 137.2, 130.4, 128.7, 128.6, 128.3, 128.2, 128.0, 127.8, 127.8, 126.4, 117.4 (COCF3), 116.9 (COCF3), 101.8, 100.3, 99.9, 98.5, 93.5, 77.9, 76.2, 75.8, 74.7, 73.7, 73.4, 72.7, 72.5, 72.4, 71.9, 70.9, 70.1, 69.8, 69.4, 69.3, 68.7, 66.5, 64.8, 62.4, 58.5, 52.6, 51.3, 38.0, 29.8, 27.6, 20.8, 20.6, 20.5, 20.4 (2C), 15.0; ESI-Q-TOF (positive mode) calculated value C 67 H 78 F6N2O 29 + [M+NH4] + m / z 1506.4938, observed value 1506.4886.

[0118] Synthesis of ethyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid, methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-α-D-galactopyranose, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Ethyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyranose-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (660 mg, 0.44 mmol) was dissolved in dichloromethane / methanol (5.0 mL / 1.0 mL). Hydrazine acetate (200 mg, 2.22 mmol, 5.0 equiv.) was added under ice bath conditions, and the mixture was allowed to warm to room temperature and react overnight. After detecting the completion of the reaction by TLC, the reaction solution was diluted with dichloromethane, and the organic phase was washed successively with 1M hydrochloric acid solution, saturated sodium bicarbonate solution, and saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH=50:1) to give a white solid (450 mg, 73%). f = 0.52 (DCM / MeOH = 20:1); 1H NMR (400 MHz, CDCl3, TMS) δ 8.33 (1H, d, J = 7.5 Hz), 8.04 (1H, d, J = 9.1 Hz), 7.56 (2H, dd, J = 7.5, 2.1 Hz), 7.46-7.38 (3H, m), 7.34-7.24 (9H, m), 7.17 (2H, dd, J = 7.3, 2.3 Hz), 5.54 (1H, s), 5.23-5.00 (3H, m), 4.93 (1H, t, J = 8.5 Hz), 4.88 (1H, d, J = 8.3 Hz), 4.75 (1H, d, J = 11.3 Hz), 4.66 (1H, s), 4.63 (1H, d, J = 4.7 Hz), 4.58 (1H, t, J = 9.5 Hz), 4.50-4.29 (5H, m), 4.26-4.14 (3H, m), 4.06 (1H, dd, J = 10.2, 3.4 Hz), 4.00 (1H, d, J = 11.9 Hz), 3.97-3.85 (4H, m), 3.76 (1H, d, J = 2.7 Hz), 3.71 (3H, s), 3.67 (2H, s), 3.62-3.53 (2H, m), 3.50 (1H, d, J = 2.8 Hz), 3.45-3.37 (1H, m), 3.36 (1H, s), 3.02-2.91 (1H, m), 2.10 (3H, s), 2.04 (3H, s), 1.99 (6H, d, J = 0.9 Hz), 1.96 (3H, s), 1.16 (3H, t, J = 7.0 Hz); 13C NMR (100 MHz, CDCl3, TMS) δ 171.1, 170.0, 169.9, 169.6, 169.4, 167.0, 158.2 (COCF3), 157.8 (COCF3), 138.0, 137.8, 137.4, 130.0, 128.7, 128.6, 128.4, 128.0, 127.9, 126.3, 117.2 (COCF3), 114.3 (COCF3), 101.2, 100.3, 99.6, 99.4, 95.3, 77.7, 76.2, 76.1, 74.8, 73.4, 72.5, 72.4, 72.1, 71.3, 71.0, 70.9, 69.4, 69.3, 68.5, 66.4, 64.7, 62.7, 62.4, 57.5, 52.7, 52.1, 20.9, 20.6, 20.5, 20.4, 20.3, 14.8.

[0119] Synthesis of ethyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid, methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-α-D-pyrangalacturonic acid, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Ethyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronate, methyl(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-α-D-galactopyranose, (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (430 mg, 0.31 mmol) was dissolved in dichloromethane / water (8.0 mL / 4.0 mL). 2,2,6,6-tetramethylpiperidine-nitrogen-oxide (20 mg, 0.13 mmol, 0.4 equiv.) and diacetoxyiodobenzene (200 mg, 0.62 mmol, 2.0 equiv.) were added sequentially under ice bath conditions. The mixture was allowed to warm to room temperature and react overnight. After detecting the completion of the reaction by TLC, the reaction solution was diluted with dichloromethane, and the organic phase was washed with saturated sodium thiosulfate solution, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH=50:1) to give a pale yellow solid (320 mg, 74%). f = 0.19 (DCM / MeOH = 30:1); 1 H NMR (400 MHz, DMSO-d6, TMS) δ7.56 (2H, d, J = 7.4 Hz), 7.45-7.10 (15H, m), 5.70 (1H, s), 5.28 (1H, s), 5.19 (1H, t, J = 9.3 Hz), 4.91 (1H, t, J = 9.7 Hz), 4.83-4.49 (7H, m), 4.49-4.26 (6H, m), 4.25-3.69 (13H, m), 3.65 (3H, s), 3.57 (2H, s), 2.01-1.95 (9H, m), 1.94 (3H, s), 1.88 (3H, s), 1.07 (3H, b); 13C NMR (100 MHz, DMSO-d6, TMS) δ 170.6, 169.9, 169.8, 169.7 (2C), 167.6, 157.0 (COCF3), 156.7 (COCF3), 139.5, 138.9 (2C), 138.8 (2C), 128.7, 128.4, 128.1, 128.0, 127.9, 126.4, 117.7 (COCF3), 114.8 (COCF3), 100.1 (2C), 100.0 (2C), 75.4, 72.0, 71.8, 71.2, 70.7, 69.8, 69.1(2C), 68.0, 66.4, 64.7, 62.4, 53.1, 20.9, 20.8, 20.7, 20.6, 20.5, 15.4; ESI-Q-TOF (positive mode) calculated value C 66 H 76 F6N2O 29 + [M+NH4] + m / z 1422.4363, observed value 1422.4349.

[0120] Synthesis of ethyl β-D-glucopyranosiduronic acid-(1→3)-2-deoxy-2-acetylamino-β-D-glucopyranose-(1→2)-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-acetylamino-α,β-D-galactopyranose In the same manner as in Example 3, CP-Et was obtained in two steps from I-21-Et. [ka] [ka]

[0121] Example 5 Synthesis of isopropyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-β-D-galactopyranose [ka] Under argon gas protection, p-tolyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-1-thio-β-D-galactopyranose (2.0 g, mmol), N-iodosuccinimide (1.24 g, mmol, equiv.), and 4 Å molecular sieves were dissolved in anhydrous dichloromethane (30 mL), and isopropanol (1.0 mL, mmol, equiv.) was added. The mixture was stirred at room temperature for 2 hours, then the temperature was lowered to -20°C, and trifluoromethanesulfonic acid (0.11 mL, mmol, equiv.) was added dropwise. The mixture was stirred for 3 hours, then transferred to room temperature, and allowed to react overnight. After detecting the completion of the reaction by TLC, an appropriate amount of triethylamine was added to quench the reaction, and the mixture was filtered through molecular sieves with diatomaceous earth. The cake was washed several times with dichloromethane. The filtrates were combined, concentrated under reduced pressure, and purified by column chromatography (petroleum ether / EtOAc = 3:1) to give a white solid (1.72 g, 98%). f = 0.49 (petroleum ether / EtOAc = 1:1); 1 H NMR (400 MHz, CDCl3, TMS) δ 6.60 (1H, d, J = 8.7 Hz, NH), 5.32 (1H, d, J = 2.1 Hz), 5.28 (1H, dd, J = 11.2, 3.4 Hz), 4.69 (1H, d, J = 8.3 Hz), 4.16-4.03 (2H, m), 4.02-3.93 (1H, m), 3.92-3.80 (2H, m), 2.09 (3H, s), 1.98 (3H, s), 1.93 (3H, s), 1.18 (d, J = 6.1 Hz, 3H), 1.06 (d, J = 6.1 Hz, 3H); 13 C NMR (100 MHz, CDCl3, TMS) δ 170.61, 170.53, 170.28 ,157.5,117.2, 99.19, 73.18, 70.70, 69.42, 66.58, 61.50, 52.40, 23.24, 21.72, 20.66, 20.47.

[0122] Synthesis of isopropyl 2-deoxy-2-trifluoroacetylamino-β-D-galactopyranose [ka] Isopropyl 2-deoxy-2-trifluoroacetylamino-3,4,6-tris-O-acetyl-β-D-galactopyranose (1.71 g, 3.86 mmol) was dissolved in methanol (50.0 mL), and an appropriate amount of sodium methanol was added to adjust the pH to 9-10. The reaction was allowed to proceed with stirring at room temperature for 2 hours. After the completion of the reaction was detected by TLC, the reaction solution was neutralized to pH 7 by adding cationic resin, filtered, and the filtrate was concentrated under reduced pressure to dryness, yielding a yellow syrup. f =0.57 (DCM / MeOH=5:1) and used directly in the next reaction.

[0123] Synthesis of isopropyl 2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, isopropyl 2-deoxy-2-trifluoroacetylamino-β-D-galactopyranose (1.22 g, 3.86 mmol) and (+)-camphorsulfonic acid (1.60 g, 6.89 mmol, 1.8 equiv.) were dissolved in anhydrous acetonitrile (40.0 mL), and benzaldehyde dimethyl acetal (3.87 mL, 25.7 mmol, 6.6 equiv.) was added. The temperature was raised to 40 °C and the reaction was carried out overnight. After the completion of the reaction was confirmed by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The reaction solution was concentrated under reduced pressure and purified by column chromatography (petroleum ether / EtOAc = 2:1) to obtain the compound as a white solid (1.12 g, 71%). f =0.55 (petroleum ether / acetone = 1:2).

[0124] Isopropyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, p-tolyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-1-thio-β-D-galactopyranose (227 mg, 0.33 mmol, 1.3 equiv.) and isopropyl 2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (103 mg, 0.25 mmol) were dissolved in anhydrous dichloromethane / N,N -dimethylformamide (5.0 mL / 1.0 mL), 4Å molecular sieves (400 mg) were added, and the mixture was stirred at room temperature for 2 hours. After cooling to 0 ° C, N-iodosuccinimide (100 mg, 0.44 mmol, 1.7 equiv.) and silver trifluoromethanesulfonate (30 mg, 0.12 mmol, 0.5 equiv.) were added sequentially. The mixture was stirred at 0 ° C for 2 hours, then allowed to warm to room temperature and react overnight. After detecting the completion of the reaction by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The molecular sieves were removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure and purified by column chromatography (petroleum ether / EtOAc = 1:1) to obtain compound I-12 (210 mg, 86%) as a white solid. R f = 0.61 (DCM / MeOH = 20:1); 11H NMR (400 MHz, CDCl3, TMS) δ 7.61 - 7.50 (3H, m), 7.41 - 7.22 (13H, m), 6.96 (2H, d, J = 8.5 Hz), 6.64 (2H, d, J = 8.6 Hz), 5.54 (1H, s), 5.21 (1H, d, J = 3.6 Hz), 5.00 - 4.92 (2H, m), 4.78 (1H, d, J = 11.7 Hz), 4.66 (1H, d, J = 11.8 Hz), 4.55 (1H, d, J = 11.4 Hz), 4.47 (2H, dd, J = 11.8, 2.3 Hz), 4.42 (1H, d, J = 3.4 Hz), 4.35 - 4.24 (2H, m), 4.19 (1H, dd, J = 11.6, 4.0 Hz), 4.13 - 4.0 (4H, m), 3.96 (1H, p, J = 6.3 Hz), 3.89 (1H, dd, J = 10.0, 2.7 Hz), 3.84 (1H, b), 3.79 - 3.71 (4H, m), 3.48 (1H, s), 2.91 - 2.80, 2.75 - 2.42 (4H, m), 2.19 (3H, s), 1.23 (3H, d, J = 6.1 Hz), 1.10 (3H, d, J = 6.0 Hz); 13 13C NMR (百 MHz, CDCl3, TMS) δ 208.5, 172.5, 158.9, 157.3 (COCF3), 138.6, 138.3, 137.7, 130.4, 129.5, 129.0, 128.4, 128.3 (2C), 128.2, 127.7 (2C), 127.5, 126.4, 115.9 (COCF3), 113.5, 101.0, 98.2, 92.8, 78.3, 75. (COCF3), 113.5, 101.0, 98.2, 92.8, 78.3, 75.2, 74.7, 74.6, 73.4, 72.0, 71.5, 70.9, 70.7, 70.0, 69.5, 66.4, 64.1, 55.2, 53.3, 38.0, 29.8, 27.8, 23.4, 21. (positive mode) calculated value C 51 H 58 F3NO 14 It should be noted that there seems to be some formatting or content issues in the original text for item which might affect the accuracy of the translation. The "計算値C" part seems incomplete or unclear in the context. You may want to double-check the original text for any errors or missing information.+ [M+NH4] + m / z 983.3433, observed value 983.4160.

[0125] Isopropyl 3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Isopropyl 2-Op-methoxybenzyl-3,4-di-O-benzyl-6-acetylpropionyl-β-D-galactopyranose-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (714 mg, 0.86 mmol) was dissolved in dichloromethane / water (14.6 mL / 1.46 mL), and 2,3-dichloro-5,6-dicyano-p-benzoquinone (204 mg, 0.90 mmol, 1.0 equiv.) was added in batches and the mixture was allowed to react at room temperature for 1 hour. After detecting the completion of the reaction by TLC, the reaction solution was diluted with dichloromethane, and the organic phase was washed successively with saturated sodium bicarbonate solution, saturated sodium thiosulfate solution, and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH=40:1) to give a white solid (490 mg, 80%). f = 0.63 (petroleum ether / acetone = 1:1); 1H NMR (400 MHz, CDCl3, TMS) δ 7.64 (1H, d, J = 9.3 Hz), 7.60–7.47 (2H, m), 7.42–7.10 (13H, m), 5.59 (1H, s), 5.18 (1H, d, J = 3.9 Hz), 4.94 (1H, d, J = 11.5 Hz), 4.86 (1H, d, J = 11.9 Hz), 4.70 (1H, d, J = 8.3 Hz), 4.62 (1H, d, J = 11.9 Hz), 4.51 (1H, d, J = 11.5 Hz), 4.42-4.24 (3H, m), 4.20-4.02 (6H, m), 3.95 (1H, p, J = 6.2 Hz), 3.78 (1H, d, J = 7.7 Hz), 3.72 (1H, s), 3.59 (1H, dd, J = 10.0, 2.8 Hz), 3.44 (1H, s), 2.92 (1H, ddd, J =18.9, 10.0, 3.5 Hz), 2.71–2.55 (2H, m), 2.48–2.40 (1H, m), 2.20 (3H, s), 1.23 (3H, d, J = 6.2 Hz), 1.11 (3H, d, J = 6.1 Hz); 13 C NMR (100 MHz, CDCl3, TMS) δ 210.0, 172.2, 157.3 (COCF3), 138.5, 138.2, 137.3, 129.0, 128.4, 128.3 (2C), 127.8 (2C), 127.6, 116.1 (COCF3), 100.9, 98.9, 94.6, 79.6, 75.4, 74.6, 73.9, 73.1, 71.7, 70.6, 70.4, 69.4, 69.1, 66.3, 64.6, 51.6, 38.1. 29.9, 27.6, 23.4, 21.8; ESI-Q-TOF (positive mode) switchC 43 H 50 F3NO 13 + [M+NH4] + m / z 863.3578;

[0126] Synthesis of isopropyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl ester, (1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyranose, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Under argon gas protection, methyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetamino-D-glucopyranose[2,1,-d]2-oxazoline (488 mg, 0.74 mmol, 1.4 equiv.) and isopropyl 3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyran-(1→3)-2-deoxy-2-trifluoroacetamino) were mixed. Difluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (438 mg, 0.52 mmol) was dissolved in anhydrous dichloromethane (7.0 mL), 4 Å molecular sieves (700 mg) were added, and the mixture was stirred at room temperature for 2 hours, then cooled to -20 °C. Trifluoromethanesulfonic acid trimethylsilylate (26.5 μL, 0.16 mmol, 0.3 equiv.) was added, and the mixture was stirred at -20 °C for 2 hours, then allowed to warm slowly to room temperature and react overnight. After detecting the completion of the reaction by TLC, an appropriate amount of triethylamine was added dropwise to quench the reaction. The molecular sieves were removed by filtration through diatomaceous earth. The filtrate was concentrated under reduced pressure and purified by column chromatography (petroleum ether / acetone 2:1) to give a white solid (635 mg, 82%). f = 0.49 (petroleum ether / acetone 1:1); 1H NMR (400 MHz, CDCl3, TMS) δ 7.76 (2H, t, J = 9.5 Hz), 7.66-7.58 (2H, m), 7.50 - 7.23 (11H, m), 7.19-7.14 (2H, m), 5.59 (1H, s), 5.16 (1H, t, J = 9.6 Hz), 5.13-5.02 (2H, m), 4.96 (2H, dd, J = 9.4, 8.1 Hz), 4.81 (1H, d, J = 11.6 Hz), 4.74-4.51 (4H, m), 4.42 (1H, d, J = 3.5 Hz), 4.40-4.24 (6H, m), 4.20-4.10 (2H, m), 4.07 (1H, dd, J = 10.2, 3.5 Hz), 4.03-3.78 (5H, m), 3.74 (1H, d, J = 2.9 Hz), 3.72 (3H, s), 3.65 (1H, d, J = 8.0 Hz), 3.59 (1H, td, J = 6.3, 2.9 Hz), 3.45 (2H, b), 3.07-2.92 (1H, m), 2.69-2.55 (3H, m), 2.35 (1H, dt, J=16.4, 4.2 Hz), 2.20 (3H, s), 2.10 (3H, s), 2.05 (3H, s), 2.02 (3H, s), 2.00 (6H, s), 1.24 (3H, d, J = 6.2 Hz), 1.11 (3H, d, J = 6.1 Hz). 13C NMR (100 MHz, CDCl3, TMS) δ 210.2, 172.5, 170.9, 170.1, 169.9, 169.5 (2C), 167.1, 157.9 (COCF3), 157.8 (COCF3), 138.3, 138.1, 137.6, 130.3, 128.7, 128.5, 128.2, 128.1, 128.0, 127.9, 126.6, 117.0 (COCF3), 115.7 (COCF3), 101.6, 100.4, 99.1, 98.9, 94.2,77.8, 77.4, 76.3, 76.0, 74.9, 73.7, 72.9, 72.7, 72.6, 72.1, 71.8, 71.1, 70.4, 70.0, 69.5, 68.7, 66.5, 64.9, 62.5, 58.5, 52.8, 52.0, 38.1, 29.9, 27.8, 23.6, 21.9, 20.9, 20.7, 20.6; ESI-Q-TOF (positive mode) calculated value C 68 H 80 F6N2O 29 + [M+NH4] + m / z 1520.5095, observed value 1520.5051.

[0127] Synthesis of isopropyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl ester, (1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-α-D-galactopyranose, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Isopropyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-6-acetylpropionyl-α-D-galactopyranose-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (490 mg, 0.33 mmol) was dissolved in dichloromethane / ethanol (17.0 mL / 2.0 mL). Hydrazine acetate (177 mg, 1.96 mmol, 6.0 equiv.) was added under ice bath conditions, and the mixture was allowed to warm to room temperature and react overnight. After detecting the completion of the reaction by TLC, the reaction solution was diluted with dichloromethane, and the organic phase was washed successively with 1M hydrochloric acid solution, saturated sodium bicarbonate solution, and saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH=50:1) to give a white solid (436 mg, 97%). f = 0.44 (DCM / MeOH = 20:1); 1H NMR (400 MHz, CDCl3, TMS) δ 7.56 (2H, dd, J = 7.3, 2.4 Hz), 7.42-7.35 (3H, m), 7.33-7.18 (12H, m), 7.07 (1H, d, J = 8.3 Hz), 5.61 (1H, s), 5.17-5.07 (3H, m), 4.92 (1H, t, J = 8.5 Hz), 4.86 (1H, d, J = 8.4 Hz), 4.82-4.72 (3H, m), 4.61 (1H, d, J = 12.2 Hz), 4.44-4.28 (6H, m), 4.22 (1H, d, J = 9.6 Hz), 4.16 (2H, d, J = 12.5 Hz), 4.08-3.99 (3H, m), 3.96 (1H, t, J = 6.2 Hz), 3.92 (1H, d, J = 9.6 Hz), 3.78 (1H, d, J = 2.8 Hz), 3.73 (3H, s), 3.69-3.58 (3H, m), 3.51 (1H, d, J = 2.8 Hz), 3.46 (1H, s), 3.45-3.38 (1H, m), 3.34 (1H, dd, J = 10.6, 3.7 Hz), 2.12 (3H, s), 2.05 (3H, s), 2.01 (6H, s), 2.00 (3H, s), 1.23 (3H, d, J = 6.2 Hz), 1.10 (3H, d, J = 6.1 Hz); 13C NMR (100 MHz, CDCl3, TMS) δ 171.1, 170.0, 169.7, 169.4, 169.3, 166.9, 157.9 (COCF3), 157.8 (COCF3), 138.1, 137.8, 137.8, 128.6, 128.4 (2C), 128.1, 128.0 (2C), 127.7, 126.3, 117.0 (COCF3), 115.7 (COCF3), 101.0, 100.5, 100.2, 98.1, 75.6, 74.7, 72.9, 72.4, 72.2, 71.9, 71.0, 69.3, 68.2, 66.6, 62.4, 56.9, 52.8, 23.3, 21.7, 21.0, 20.6, 20.5, 20.4; ESI-Q-TOF (positive mode) calculated value C 63 H 74 F6N2O 27 + [M+NH4] + m / z 1422.4727, observed value 1422.4666.

[0128] Synthesis of isopropyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl ester, (1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose, (1→2)-3,4-di-O-benzyl-α-D-pyrangalacturonic acid, and (1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose [ka] Isopropyl 2,3,4-tris-O-acetyl-β-D-glucopyranosiduronic acid methyl-(1→3)-4,6-di-O-acetyl-2-deoxy-2-trifluoroacetylamino-β-D-glucopyranose-(1→2)-3,4-di-O-benzyl-α-D-galactopyranose-(1→3)-2-deoxy-2-trifluoroacetylamino-4,6-O-benzenemethylene-β-D-galactopyranose (413 mg, 0.29 mmol) was dissolved in dichloromethane / water (8.0 mL / 4.0 mL). 2,2,6,6-tetramethylpiperidine-nitrogen-oxide (23 mg, 0.15 mmol, 0.5 equiv.) and diacetoxyiodobenzene (189 mg, 0.59 mmol, 2.0 equiv.) were added sequentially under ice bath conditions. The mixture was allowed to warm to room temperature and react overnight. After detecting the completion of the reaction by TLC, the reaction solution was diluted with dichloromethane, and the organic phase was washed with saturated sodium thiosulfate solution, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by column chromatography (DCM / MeOH=50:1) to give a pale yellow solid (384 mg, 92%). f = 0.19 (DCM / MeOH = 30:1); 11H NMR (400 MHz, CDCl3, TMS) δ 7.62 - 7.47 (4H, m), 7.42 - 7.35 (3H, m), 7.31 - 7.16 (10H, m), 5.62 (1H, s), 5.20 (1H, s), 5.12 (2H, p, J = 9.3 Hz), 4.92 (1H, t, J = 8.2 Hz), 4.82 (1H, d, J = 8.3 Hz), 4.79 - 4.67 (3H, m), 4.63 (1H, d, J = 12.1 Hz), 4.44 (1H, d, J = 7.9 Hz), 4.41 - 4.21 (7H, m), 4.18 - 4.09 (2H, m), 4.06 (2H, d, J = 9.0 Hz), 4.01 - 3.90 (4H, m), 3.83 (1H, d, J = 10.3Hz), 3.71 (3H, s), 3.65 - 3.56 (1H, m), 3.33 (2H, b), 2.11 (3H, s), 2.07 - 1.94 (12H, m), 1. (3H, d, J = 6.1 Hz), 1.07 (3H, d, J = 6.0 Hz); 13 13C NMR (100 MHz, CDCl3, TMS) δ 171.4, 170.4, 170.0, 169.9, 169.6, 169.4, 167.0, 157.9 (COCF3), 157.5 (COCF3), 137.9, 137.7, 137.4, 129.7, 128.6, 128.5, 128.3, 128.2, 127.8 (2C), 126.4, 117.1 (COCF3), 114.3 (COCF3), 101.1, 100.3, 98.1, 76.4, 75.8, 75.4, 73.1, 72.4 (2C), 72.0, 70.9, 69.4, 69.2, 6, 66.4, 62.4, 57.0, 53.1, 52.8, 23.3, 21.7, 20.8, 20.6, 20.5, 20.4(2C); ESI-Q-TOF (positive mode) calculated value C 63 1H 72 F₆N₂O 28 + [M + NH₄] +m / z 1436.4520, observed value 1436.4529.

[0129] Synthesis of isopropyl β-D-glucopyranosiduronic acid-(1→3)-2-deoxy-2-acetylamino-β-D-glucopyranose-(1→2)-α-D-pyrangalacturonic acid-(1→3)-2-deoxy-2-acetylamino-α,β-D-galactopyranose In the same manner as in Example 3, CP-Pr was obtained in two steps from I-21-Pr. [ka] [ka]

[0130] Test Example 1 In vitro anti-inflammatory activity test Effect of compounds CP-1 / CP-2 on NO production in LPS-induced RAW264.7 cells The cells were divided into a blank control group, an LPS group, and groups containing compounds CP-1 and CP-2 at different concentrations (0.01, 0.03, 0.1, 0.3, 1, 3, and 10 μM). Three multiwells were set up for each group, and each well contained 100 μL of 1 × 10 cells. 5 Cells were seeded into 96-well cell culture plates at a density of 1 / 3 cells and incubated overnight at 37°C. The following day, different concentrations of compounds were added for 2 hours, followed by 100 ng / mL lipopolysaccharide (LPS) and incubation at 37°C for 24 hours. After incubation, nitric oxide levels in the cells were measured according to the nitric oxide kit instructions. As shown in Figure 1, nitric oxide release was significantly enhanced after 24 hours of treatment with 100 ng / mL LPS compared to the blank control group. Both CP-1 and CP-2 dose-dependently inhibited nitric oxide release compared to the LPS control group, with the difference being statistically significant.

[0131] Effect of compounds CP-1 / CP-2 on PGE2 production in LPS-induced RAW264.7 cells The cells were divided into a blank control group, an LPS group, and groups containing compounds CP-1 and CP-2 at different concentrations (0.01, 0.03, 0.1, 0.3, 1, 3, and 10 μM). Three multiwells were set up for each group, and each well contained 100 μL of 1 × 10 cells. 5 Cells were seeded into 96-well cell culture plates at a density of 1 / 3 cells per well and incubated overnight at 37°C. The following day, cells were treated with various concentrations of compounds for 2 hours, followed by the addition of 100 ng / mL lipopolysaccharide (LPS) solution and incubation at 37°C for 24 hours. After incubation, the cells were centrifuged at 300 xg for 5 minutes at 4°C to collect the cell supernatant. The prostaglandin E2 levels in the supernatant were measured according to the prostaglandin E2 kit instructions. As shown in Figure 2, after 24 hours of treatment with 100 ng / mL LPS, prostaglandin E2 release was significantly enhanced compared to the blank control group. Both CP-1 and CP-2 dose-dependently inhibited prostaglandin E2 release compared to the LPS model group, with statistically significant differences.

[0132] Effects of compounds CP-1 / CP-2 on the release of IL-1β, IL-6, and TNF-α in LPS-induced RAW264.7 cells The cells were divided into a blank control group, an LPS group, and groups containing compounds CP-1 and CP-2 at different concentrations (0.01, 0.03, 0.1, 0.3, 1, 3, and 10 μM). Three multiwells were set up for each group, and each well contained 100 μL of 1 × 10 cells. 5Cells were seeded into 96-well cell culture plates at a density of 1 / 3 cells per well and incubated overnight at 37°C. The following day, cells were treated with various concentrations of compounds for 2 hours, followed by the addition of 100 ng / mL lipopolysaccharide (LPS) solution and incubation at 37°C for 24 hours. After incubation, the cells were centrifuged at 300 xg for 5 minutes at 4°C to collect the cell supernatants. IL-1β, IL-6, IL-10, and TNF-α concentrations were measured according to the corresponding ELISA kit instructions. As shown in Figure 3, after 24 hours of treatment with 100 ng / mL LPS, the release of IL-1β, IL-6, and TNF-α was significantly enhanced compared to the blank control group. Compared to the LPS control group, both CP-1 and CP-2 dose-dependently inhibited the release of IL-1β, IL-6, and TNF-α, with statistically significant differences.

[0133] Test Example 2 Effects of compounds CP-1 / CP-2 on iNOS and COX-2 protein expression in LPS-induced RAW264.7 cells The cells were divided into a blank control group, an LPS group, and groups containing compounds CP-1 and CP-2 at different concentrations (compound concentrations: 1, 3, 10, 30, and 100 μM). Three multiwells were set up for each group, and each well contained 100 μL of the cells. Each well contained 4 × 10 cells. 5Cells were seeded at a density of 1 / 3 cells into 6-well cell culture plates and incubated overnight at 37°C. The following day, cells were treated with various concentrations of compounds for 2 hours, followed by the addition of 100 ng / mL lipopolysaccharide (LPS) solution and incubation at 37°C for 24 hours. After incubation, the expression of iNOS and COX-2 proteins in the cells was measured using Western blot analysis. The cell supernatant was discarded, and the cells were washed three times with pre-chilled PBS. RIPA cell lysis solution containing PMSF was added and incubated on ice for 15 minutes to thoroughly lyse the cells. The cells were centrifuged at 300xg for 5 minutes at 4°C, and the cell supernatant was collected. The protein concentration was measured according to the BCA protein quantification kit instructions. The proteins were then denatured by boiling in a metal bath at 100°C for 5 minutes. Proteins were separated by electrophoresis, transferred to a membrane, and sealed at room temperature for 1 hour. Primary antibody incubation was performed overnight at 4°C. The following day, the membrane was washed three times with TBST and incubated with secondary antibody at room temperature for 1 hour. After washing the membrane three times with TBST, chemiluminescence solution was added and the membrane was placed in a chemiluminescence gel imaging system for imaging. Western blot results, as shown in Figure 4, showed that after 24 hours of treatment with 100 ng / mL lipopolysaccharide, the expression of iNOS and COX-2 proteins in the cells was significantly enhanced compared to the blank control group. Compared to the LPS model group, both CP-1 and CP-2 dose-dependently suppressed the expression of iNOS and COX-2 proteins, with statistically significant differences.

[0134] Test Example 3 In vivo anti-inflammatory activity test Effect of compound CP-1 on survival rate in an LPS-induced mouse sepsis model A total of 60 male C57BL / 6 mice, aged 6-8 weeks and weighing 20±2 g, were selected. The mice were kept in a room with a temperature of 20-24°C and humidity of 50-60%, with free access to water and food. They were allowed to adapt for 7 days before the experiment. Mice were randomly divided into six groups: control, model, high-dose CP-1 (30 mg / kg), medium-dose (10 mg / kg), low-dose (3 mg / kg), and dexamethasone groups, each consisting of 10 mice. The high-dose CP-1 group received an intraperitoneal injection of 200 μL of CP-1 solution at a concentration of 30 mg / kg. The medium-dose group received an intraperitoneal injection of an equal volume of CP-1 solution at a concentration of 10 mg / kg. The low-dose group received an intraperitoneal injection of an equal volume of CP-1 solution at a concentration of 3 mg / kg. The dexamethasone group received an intraperitoneal injection of an equal volume of 30 mg / kg dexamethasone solution. The control group received an intraperitoneal injection of an equal volume of 0.9% saline. Except for the control group, each group received an intraperitoneal injection of 200 μL of 45 mg / kg LPS solution for molding. Each group received three doses of the drug, one each 48 hours and 24 hours before and 30 minutes after molding. After administration, the condition and survival rate of the mice were observed and recorded every 6 hours, and were continuously observed and recorded for 72 hours. As shown in the figure, the experimental results showed that the survival rate 72 hours after administration was 40% for the model group mice, 100% for the control group mice, 70% for the high-dose and low-dose CP-1 groups mice, 80% for the medium-dose CP-1 group mice, and 60% for the positive drug dexamethasone group mice.

[0135] Effect of compound CP-1 on serum cytokines in a mouse model of LPS-induced sepsis A total of 24 male C57BL / 6 mice, aged 6–8 weeks, weighing 20 ± 2 g, were selected. The mice were housed in a vivarium maintained at 20–24°C and 50–60% humidity, with free access to food and water. They were allowed to adapt for 7 days prior to the experiment. The mice were randomly divided into four groups: control, CP-1, LPS, and LPS + CP-1, each consisting of six mice. The CP-1 and LPS + CP-1 groups were intraperitoneally injected with 200 μL of CP-1 solution at a concentration of 10 mg / kg. The control and LPS groups were intraperitoneally injected with an equal volume of 0.9% saline. The LPS and LPS + CP-1 groups were subjected to molding via intraperitoneal injection of 200 μL of 25 mg / kg LPS solution. Each group received two injections, one 24 h before molding and one 30 min after molding. Twelve hours after administration, the mice were anesthetized and blood was collected from the heart. The blood was allowed to stand for 2 hours, then centrifuged at 5000 rpm for 10 minutes to collect serum. The absorbance per well was measured at a wavelength of 450 nm using a multi-function microplate reader according to the instructions in the Elisa kit, and the contents of the cytokines IL-1β, IL-6, IL-18, TNF-α, Gal-3, INF-γ, and HMGB1 were calculated using standard curves.

[0136] Effect of compound CP-Me on serum cytokines in a mouse model of LPS-induced sepsis A total of 24 male C57BL / 6 mice, 6-8 weeks old and weighing 20 ± 2 g, were selected. The mice were housed in a vivarium maintained at 20-24°C and 50-60% humidity, with free access to food and water. They were allowed to adapt for 7 days before the experiment. The mice were randomly divided into four groups: control, CP-Me, LPS, and LPS + CP-Me, each consisting of six mice. The CP-Me 10 mg / kg and CP-Me 3 mg / kg groups were intraperitoneally injected with 200 μL of CP-Me solution at concentrations of 10 mg / kg and 3 mg / kg, respectively. The control and LPS groups were intraperitoneally injected with an equal volume of 0.9% saline. The LPS and treatment groups were subjected to molding via intraperitoneal injection of 200 μL of 25 mg / kg LPS solution. Each group received two injections, once 12 hours before molding and once 30 minutes after molding. Twelve hours after administration, the mice were anesthetized and blood was collected from the heart. The blood was allowed to stand for 2 hours, then centrifuged at 5000 rpm for 10 minutes to collect serum. The absorbance per well was measured at a wavelength of 450 nm using a multi-function microplate reader according to the instructions in the Elisa kit, and the contents of cytokines IL-1β, IL-6, and TNF-α were calculated using standard curves.

[0137] HE staining and inflammation index analysis A total of 60 male C57BL / 6 mice, 6-8 weeks old and weighing 20 ± 2 g, were selected. Mice were housed in a vivarium maintained at 20-24°C and 50-60% humidity. They had free access to water and food and were allowed to adapt for 7 days before the experiment. They were randomly divided into six groups: control, LPS, CP-1 (10 mg / kg), and dexamethasone. Each group consisted of six mice. The high-dose CP-1 group received an intraperitoneal injection of 200 μL of CP-1 solution at a concentration of 30 mg / kg. The medium-dose group received an intraperitoneal injection of an equal volume of CP-1 solution at a concentration of 10 mg / kg. The low-dose group received an intraperitoneal injection of an equal volume of CP-1 solution at a concentration of 3 mg / kg. The dexamethasone group received an intraperitoneal injection of an equal volume of 30 mg / kg dexamethasone solution. The control group received an intraperitoneal injection of an equal volume of 0.9% saline. Except for the control group, all groups were given 200 μL of 45 mg / kg LPS solution by intraperitoneal injection twice, once 24 hours before and once 30 minutes after molding. Twenty-four hours after administration, mice were sacrificed by decapitation. The left lungs were removed and fixed in formalin. After fixation, they were embedded in paraffin and sectioned. Histomorphological changes were observed by iodine staining. Different histopathological changes, such as hemorrhage, neutrophil-infiltrated alveoli, increased membrane transparency, increased tissue debris, and increased heterogeneous septal layers, were scored from 0 to 4. 0 represented no damage, 1 represented less than 25% damage, 2 represented 25% to 50% damage, 3 represented 50% to 75% damage, and 4 represented greater than 75% damage. Inflammation scores were scored by three different technicians, and the average of the scores was used to determine the final score. The results showed that the LPS group showed significantly more pronounced alveolar wall thickening, alveolar shrinkage, massive pulmonary interstitial inflammatory cell infiltration, and hemorrhage than the blank group, whereas the CP-1 (10 mg / kg) group significantly alleviated LPS-induced lung injury and maintained the basic morphology of the lung tissue. The dexamethasone group also showed similar effects, but was less effective than CP-1 morphologically and may have increased the risk of hemorrhage.

[0138] Although the examples set forth in this application are as described above, the above contents are merely examples for the convenience of understanding the application and are not intended to limit the application. Those skilled in the art may make any modifications and changes to the embodiments and details without departing from the spirit and scope of the application, and the scope of protection of the application is based on the scope of the appended claims. Some embodiments are given below. Item 1 Use of a bacterial capsular oligosaccharide derivative represented by formula I or a pharmaceutically acceptable salt, solvate or prodrug thereof as an anti-inflammatory drug, comprising: [ka] In formula (I), R 1 is OH, an unsubstituted or substituted C1-C6 alkoxy group, an unsubstituted or substituted C2-C6 alkenoxy group, an unsubstituted or substituted C2-C6 alkynyloxy group, an unsubstituted or substituted C1-C6 alkylthio group, an unsubstituted or substituted C1-C6 alkanoyloxy group, or an unsubstituted or substituted areneoxy group; R 2 -OH, -N(H)-R 15 , N(R 16 )-R 17 , an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group, wherein R 15 is an amino acid residue that does not contain proline, and R 16 and R 17 together form a proline residue, R 3 and R 4 each independently represents an unsubstituted or substituted C1-C6 alkanoyl group, R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 and R 13 are each independently hydrogen, an unsubstituted or substituted C1-C6 alkanoyl group, or an unsubstituted or substituted C1-C6 alkyl group; R 14 is OH, an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group, or a pharmaceutically acceptable salt, solvate, or prodrug thereof, for use as an anti-inflammatory drug. Section 2 In formula (I), R 1 is OH, an unsubstituted or substituted C1-C6 alkoxy group, an unsubstituted or substituted C2-C6 alkenoxy group, an unsubstituted or substituted C2-C6 alkynyloxy group, an unsubstituted or substituted C1-C6 alkylthio group, an unsubstituted or substituted C1-C6 alkanoyloxy group, or an unsubstituted or substituted areneoxy group, wherein the substituted C1-C6 alkoxy group, substituted C2-C6 alkenoxy group, substituted C2-C6 alkynyloxy group, The terms "a C1-C6 alkoxy group, a substituted C1-C6 alkylthio group, a substituted C1-C6 alkanoyloxy group, and a substituted areneoxy group" mean that one or more hydrogen atoms in a C1-C6 alkoxy group, a C2-C6 alkenoxy group, a C2-C6 alkynyloxy group, a C1-C6 alkylthio group, a C1-C6 alkanoyloxy group, or an areneoxy group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkoxy group, a halogen atom, a nitro group, a cyano group, an acetyl group, a propionyl group, and a phenyl group; R 2 -OH, -N(H)-R 15 , N(R 16 )-R 17 , an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group, wherein R 15 is an amino acid residue that does not contain proline, and R 16 and R 17 together form a proline residue, and the substituted C1-C6 alkoxy group and substituted areneoxy group mean that one or more hydrogen atoms in the C1-C6 alkoxy group or areneoxy group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkoxy group, a halogen atom, a nitro group, a cyano group, and a phenyl group; R 3 and R 4 each independently represents an unsubstituted or substituted C1-C6 alkanoyl group, wherein the substituted C1-C6 alkanoyl group means that one or more hydrogen atoms in the C1-C6 alkanoyl group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkanoyl group, a halogen atom, a nitro group, a cyano group, an acetyl group, a propionyl group, and a phenyl group; R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 and R 13 are each independently hydrogen, an unsubstituted or substituted C1-C6 alkanoyl group, or an unsubstituted or substituted C1-C6 alkyl group, wherein the substituted C1-C6 alkanoyl group or substituted C1-C6 alkyl group means that one or more hydrogen atoms in the C1-C6 alkanoyl group or C1-C6 alkyl group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkoxy group, a halogen atom, a nitro group, a cyano group, an acetyl group, a propionyl group, and a phenyl group, and optionally the phenyl group may be substituted with one or more groups selected from the group consisting of a C1-C4 alkoxy group and a nitro group; R 14 is OH, an unsubstituted or substituted C1-C6 alkoxy group, or an unsubstituted or substituted areneoxy group, wherein the substituted C1-C6 alkoxy group and the substituted areneoxy group mean that one or more hydrogen atoms in the C1-C6 alkoxy group or the areneoxy group are substituted with a group selected from the group consisting of a hydroxyl group, a C1-C6 alkoxy group, a halogen atom, a nitro group, a cyano group, and a phenyl group. Section 3 In the formula (I), R 1 is OH, an unsubstituted C1-C6 alkoxy group, a C1-C6 alkoxy group substituted with benzene, or an unsubstituted C2-C6 alkeneoxy group, preferably R 1 is OH, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an allyloxy group, or a benzyloxy group. Section 4 In the formula (I), R 2 -OH, -N(H)-R 15 , N(R 16 )-R 17 , an unsubstituted C1-C6 alkoxy group, or a C1-C6 alkoxy group substituted by benzene, where R 15 is an amino acid residue that does not contain proline, and R 16 and R 17 together form a proline residue, preferably R 2 is OH, methoxy group or -N(H)-R 15 where R 15 is a threonine residue. Section 5 In the formula (I), R 3 and R 4 are each independently an unsubstituted or substituted C1-C6 alkanoyl group, and the substituted C1-C6 alkanoyl group means that one or more hydrogen atoms in the C1-C6 alkanoyl group are substituted with a group selected from the group consisting of halogen, a nitro group, a cyano group, an acetyl group, a propionyl group, and a phenyl group, and preferably R 3 and R 4 and each independently represent an acetyl group or a trifluoroacetyl group. Section 6 In the formula (I), R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 and R 13 are each independently hydrogen, an unsubstituted C1-C6 alkanoyl group, a C1-C6 alkanoyl group substituted with benzene, or a substituted phenylmethyl group, and preferably, R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 and R 13 and each independently represents hydrogen, an acetyl group, a benzyl group, or a 4-methoxybenzyl group. Section 7 In the formula (I), R 14 is OH or an unsubstituted or substituted C1-C6 alkoxy group, preferably R 14 is an OH or methoxy group. Section 8 The anti-inflammatory effect means suppressing the production of nitric oxide and prostaglandin E2, and / or inhibiting the expression of nitric oxide synthase and cyclooxidase 2 proteins, and / or reducing the release of interleukin-1β, interleukin-6, and tumor necrosis factor-α, and is preferably for the treatment of sepsis. Section 9 1. A method for preventing or treating inflammation, comprising administering to an individual in need thereof a therapeutically effective amount of a bacterial capsular oligosaccharide derivative or a pharmaceutically acceptable salt, solvate, or prodrug thereof, wherein said derivative is represented by Formula I:

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Claims

1. Use of a bacterial capsular oligosaccharide derivative represented by formula I or a pharmaceutically acceptable salt or solvate thereof in the preparation of an anti-inflammatory drug, comprising: 【Chemical 1】 In formula (I), R 1 is OH, methoxy, ethoxy, n-propoxy, isopropoxy, allyloxy, or benzyloxy; R 2 -OH or -N(H)-R 15 wherein R 15 is a threonine residue; R3 and R4 are each independently an acetyl group; R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 and R 13 are each independently hydrogen; R 14 Use of a bacterial capsular oligosaccharide derivative or a pharmaceutically acceptable salt or solvate thereof, wherein is OH, in the preparation of an anti-inflammatory drug.

2. The derivative is compound CP-1. 【Chemistry 2】 2. The use according to claim 1.

3. The derivative is compound CP-2. 【Chemistry 3】 2. The use according to claim 1.

4. The derivative is the compound CP-Me. 【Chemistry 4】 2. The use according to claim 1.

5. The derivative is the compound CP-Et. 【Chemistry 5】 2. The use according to claim 1.

6. The derivative is the compound CP-Pr. 【Chemistry 6】 2. The use according to claim 1.

7. The anti-inflammatory means suppressing the production of nitric oxide and prostaglandin E2, and / or inhibiting the expression of nitric oxide synthase and cyclooxidase 2 proteins, and / or reducing the release of interleukin-1β, interleukin-6 and tumor necrosis factor-α, preferably for the treatment of sepsis, according to claim 1.

8. A method for producing the derivative in the use according to any one of claims 1 to 7, comprising the steps of: a step of reacting a compound of formula (I-13) with a compound of formula (I-18) to obtain a compound (I-19), 【Chemistry 7】 A method for producing the derivative, wherein in the compound of formula (I-13), formula (I-18), or formula (I-19), Ac is an acetyl group, Ph is a phenyl group, Bn is a benzyl group, Me is a methyl group, TFA is a trifluoroacetyl group, and Lev is an acetylpropionyl group.

9. Compound CP-1, 【Chemistry 8】 Bacterial capsular oligosaccharide derivatives.

10. Compound CP-2, 【Chemistry 9】 Bacterial capsular oligosaccharide derivatives.

11. The compound CP-Me, 【Chemistry 10】 Bacterial capsular oligosaccharide derivatives.

12. The compound CP-Et. 【Chemistry 11】 Bacterial capsular oligosaccharide derivatives.

13. The compound CP-Pr, 【Chemistry 12】 Bacterial capsular oligosaccharide derivatives.

14. A pharmaceutical composition comprising the derivative according to any one of claims 9 to 13.

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