2-deoxysugar glycosylation reaction catalyst, method for catalyzing glycosylation of glycal donor and application of 2-deoxysugar glycosylation reaction catalyst

Abstract

The invention belongs to the technical field of sugar chemistry, and relates to a 2-deoxysugar glycosylation reaction catalyst, a method for catalyzing glycosylation of a glycal donor and application. According to the invention, mercury trifluoromethanesulfonate is used as a catalyst, the operation is simple, the reaction condition is mild, other ligands and auxiliary catalysts are not needed, the substrate application range is wide, the reaction yield and stereoselectivity are high, and a product mainly having alpha-configuration is obtained. According to the present invention, mercury trifluoromethanesulfonate is firstly bonded to the C-2 site of a syrup donor to form a catalyst-donor adduct, due to the spatial and electronic effects, the acceptor attacks the heterogenous carbon from the alpha surface through the mercury (II) mediated auxiliary effect, and the released protons then split the C-Hg bond so as to regenerate mercury trifluoromethanesulfonate and return it to the catalytic cycle, the 2-deoxyglucose glycosylation reaction catalyzed by the mercury trifluoromethanesulfonate is realized. According to the method, the binding capacity of mercury trifluoromethanesulfonate and donor double bonds is fully utilized, and the method is suitable for construction of high-stereoselectivity glucosidic bonds of various monohydroxyl receptors.

Description

Technical Field

[0001] The invention belongs to the technical field of sugar chemistry and relates to a 2-deoxysugar glycosidation reaction catalyst, a method for catalyzing the glycosidation of a sugar ene donor and an application thereof. Background Art

[0002] The information disclosed in this background technology section is only intended to enhance the understanding of the overall background of the invention, and should not necessarily be regarded as an admission or any form of suggestion that the information constitutes the prior art already known to a person skilled in the art.

[0003] 2-Deoxysugar is an important component of many natural products and drugs. Due to the lack of substituents at the C-2 position of 2-deoxysugar, the construction of glycosidic bonds of 2-deoxysugar becomes a huge challenge. Glycosylation reaction is the most critical reaction in the synthesis of 2-deoxysugar compounds. It is the most important and common chemical reaction in sugar chain extension and sugar structural unit assembly. How to construct glycosidic bonds of 2-deoxysugar with high yield and high stereoselectivity is one of the basic issues in sugar chemistry research and also the biggest challenge in glycosylation reaction.

[0004] Transition metal-catalyzed glycosidation is an important method for the synthesis of 2-deoxypolysaccharides. Due to the intrinsic properties of transition metal salts, a variety of regio- and stereo-selective glycosidation methods have been developed. Therefore, the continued exploration of new catalytic properties of inexpensive and readily available metal salts remains of current interest in sugar chemistry. Mercury salts were introduced into sugar chemistry decades ago as promoters for the activation of glycosyl halides and thioglycosides; however, these methods typically consume excess or at least stoichiometric amounts of mercury salts. Due to the toxicity and environmental impact of mercury salts, it is desirable to reduce the amount of mercury used, which can be achieved through catalytic processes.

[0005] Mercury salts have been found to catalyze the activation of 2-deoxyglycone donors to produce glycoside products in a highly stereoselective manner. It is of great significance to find catalysts with better performance in transition metal catalysis of 2-deoxyglycone donors. Summary of the invention

[0006] In order to solve the deficiencies of the prior art, the purpose of the present invention is to provide a 2-deoxy sugar glycosidation reaction catalyst, a method for catalyzing the glycosidation of a sugar ene donor, and an application thereof. The 2-deoxy sugar glycosidation reaction catalyst provided by the present invention can achieve high yield and high stereoselectivity in the construction of a 2-deoxy sugar glycosidic bond. The present invention is based on mercuric trifluoromethanesulfonate as a glycosidation reaction catalyst. Mercuric trifluoromethanesulfonate first binds to the C-2 position of the sugar ene donor to form a catalyst-donor adduct. Due to spatial and electronic effects, the acceptor attacks the anomeric carbon from the α face through the auxiliary effect mediated by mercury (II), and the released proton subsequently splits the C-Hg bond, thereby regenerating mercuric trifluoromethanesulfonate and returning it to the catalytic cycle, thereby achieving a 2-deoxy sugar glycosidation reaction catalyzed by mercuric trifluoromethanesulfonate. A highly stereoselective 2-deoxy glycosidation product with an α-configuration as the main component can be provided by the sugar ene donor.

[0007] In order to achieve the above object, the present invention provides the following technical solutions:

[0008] In a first aspect, a 2-deoxyglycosidation reaction catalyst is provided, wherein the catalyst is mercuric trifluoromethanesulfonate.

[0009] In a second aspect, a use of mercuric trifluoromethanesulfonate as a catalyst in a 2-deoxyglycosidation reaction.

[0010] In a third aspect, a method for catalyzing the glycosidation of a sugar ene donor is provided, wherein mercuric trifluoromethanesulfonate is used as a catalyst to catalyze the glycosidation reaction of the sugar ene donor and an acceptor to obtain a 2-deoxyglycosidation product.

[0011] The sugar ene donor of the present invention includes a 2-deoxy sugar ene donor, and other hydroxyl groups of the 2-deoxy sugar ene donor can be replaced by different protective groups or connected to other structural units. In some embodiments, the sugar ene donor is any one of compounds 1-5, and the chemical structures of compounds 1-5 are shown below;

[0012]

[0013] The receptor described in the present invention is a compound having a monohydroxy structure. In some embodiments, the receptor is any one of compounds AJ. The chemical structures of compounds AJ are shown below:

[0014]

[0015] In some embodiments, the molar ratio of the acceptor, the glycoene donor, and mercuric trifluoromethanesulfonate is 1:1.10-1.30:0.09-0.11.

[0016] In some embodiments, in an inert atmosphere, the acceptor, the glycoene donor and the molecular sieve are added to an anhydrous solvent, stirred uniformly at a temperature of -2 to 2° C., and then mercuric trifluoromethanesulfonate is added to carry out a glycosidation reaction.

[0017] Specifically, the solvent is toluene (Toluene) or a mixture of toluene and dichloromethane (DCM) (denoted as Toluene / DCM). Studies have shown that different acceptors and different glycoene donors require different anhydrous solvents to achieve high coupling yields and high α-selectivity. When the solvent is Toluene, compound A, compound B, compound D, compound E, compound F, and compound J are used as acceptors, with high coupling yields and high α-selectivity, even for acceptors containing secondary hydroxyl groups and having low reactivity due to steric hindrance, the reaction can proceed well. The results of the glycosidation reaction are shown below:

[0018]

[0019] When the solvent is Toluene / DCM, compound 1 and compound 4 are used as glycoene donors, and compound C, compound G, compound H, and compound I are used as acceptors, with high coupling yield and high α-selectivity. For L-serine and L-threonine, the reaction can also proceed well. The glycosylation reaction results are shown below:

[0020]

[0021]

[0022] The precipitate was filtered off; the organic layer was washed with NaHCO3 solution and NaCl solution, and dried over Na2SO4, filtered and the solvent was removed under reduced pressure distillation; the resulting residue was purified by silica gel column chromatography to give the corresponding 2-deoxyglycosylated product.

[0023] In a fourth aspect, a use of the above-mentioned 2-deoxyglycosidation reaction catalyst or the method for catalyzing the glycosidation of a sugar ene donor in constructing an O-glycosidic bond of a 2-deoxysaccharide substance.

[0024] In some embodiments, 2-deoxy polysaccharides are prepared by constructing O-glycosidic bonds of 2-deoxy sugars.

[0025] Specifically, under the catalytic action of mercuric trifluoromethanesulfonate, compound 2 and compound A are subjected to glycosylation reaction to prepare compound 2A; compound 2A is deprotected by TBDPS to obtain compound 6; under the catalytic action of mercuric trifluoromethanesulfonate, compound 2 and compound 6 are subjected to glycosylation reaction to prepare compound 7; compound 7 is deprotected by TBDPS to obtain compound 8; and under the catalytic action of mercuric trifluoromethanesulfonate, compound 2 and compound 8 are subjected to glycosylation reaction to prepare compound 9. The glycosylation reaction is shown below:

[0026]

[0027] The "equivalent" in the present invention refers to the ratio of the amounts of substances when substances interact with each other, such as: donor (1.2 equivalents), acceptor (1.0 equivalents) means that the amount ratio of the donor compound to the acceptor compound in the reaction is 1.2:1.

[0028] The beneficial effects of one or more of the above technical solutions of the present invention are:

[0029] (1) The present invention uses mercuric trifluoromethanesulfonate as a catalyst for 2-deoxyglycosidation reaction, which has the advantages of high yield and stereoselectivity. In the technical scheme provided by the present invention, mercuric trifluoromethanesulfonate is combined with the C-2 position of the sugar ene donor to form a catalyst-donor adduct. Due to the spatial and electronic effects, the acceptor attacks the anomeric carbon from the α face through the auxiliary effect mediated by mercury (II), and the released proton subsequently splits the C-Hg bond, thereby regenerating mercuric trifluoromethanesulfonate and returning it to the catalytic cycle, thereby realizing the 2-deoxyglycosidation reaction catalyzed by mercuric trifluoromethanesulfonate. The sugar ene donor can provide high stereoselectivity with α-configuration as the main component, and the 2-deoxyglycosidation product can be obtained in high yield.

[0030] (2) The present invention uses mercuric trifluoromethanesulfonate as a catalyst for 2-deoxyglycosidation reaction, which has the advantage of a wide range of substrate applications. The mercuric trifluoromethanesulfonate catalytic method of the present invention can be widely applied to glucose, galactose, and fucose glycoside donors, and provides a wide range of glycosyl acceptors, all of which achieve high glycoside yields and stereoselectivity.

[0031] (3) The present invention uses mercuric trifluoromethanesulfonate as a catalyst for 2-deoxyglycosidation reaction, which has the advantages of cheap and easy catalyst availability, mild reaction conditions, and fast reaction speed. The mercuric trifluoromethanesulfonate catalyst of the present invention is cheap and easy to obtain, and has a good catalytic effect on the sugar ene donor. Under the condition of using only a catalytic amount of mercuric trifluoromethanesulfonate catalyst and no other ligands and auxiliary catalysts, the glycosidation reaction can be completed at 0°C and within 10 minutes to obtain a 2-deoxyglycosidation product with high yield and high stereoselectivity. BRIEF DESCRIPTION OF THE DRAWINGS

[0032] The accompanying drawings in the specification, which constitute a part of the present invention, are used to provide a further understanding of the present invention. The exemplary embodiments of the present invention and their descriptions are used to explain the present invention and do not constitute improper limitations on the present invention.

[0033] Figure 1 : Compound 1Aα H NMR spectrum;

[0034] Figure 2 : H NMR spectrum of compound 1Bα;

[0035] Figure 3 : Cα H NMR spectrum of compound 1;

[0036] Figure 4 : Dα H NMR spectrum of compound 1;

[0037] Figure 5 : H NMR spectrum of compound 1Eα;

[0038] Figure 6 : Fα H NMR spectrum of compound 1;

[0039] Figure 7 : Gα H NMR spectrum of compound 1;

[0040] Figure 8 : Hα NMR spectrum of compound 1;

[0041] Fig. 9 : H NMR spectrum of compound 1Iα;

[0042] Fig.10 : Jα H NMR spectrum of compound 1;

[0043] Fig.11 : Compound 2Aα H NMR spectrum;

[0044] Fig.12 : Fα H NMR spectrum of compound 2;

[0045] Fig.13 : Compound 3Aα H NMR spectrum;

[0046] Fig.14 : Fα H NMR spectrum of compound 3;

[0047] Fig.15 : α-H NMR spectrum of compound 4A;

[0048] Fig.16 : H NMR spectrum of compound 4Eα;

[0049] Fig.17 : Fα H NMR spectrum of compound 4;

[0050] Fig.18 : H NMR spectrum of compound 4Gα;

[0051] Fig.19 : Compound 5Aα H NMR spectrum;

[0052] Fig. 20 : Fα H NMR spectrum of compound 5;

[0053] Fig.21 : H NMR spectrum of compound 6;

[0054] Fig. 22 : H NMR spectrum of compound 7;

[0055] Fig.23 : H NMR spectrum of compound 8;

[0056] Fig.24 : H NMR spectrum of compound 9. DETAILED DESCRIPTION

[0057] In order to enable those skilled in the art to more clearly understand the technical solution of the present invention, the technical solution of the present invention will be described in detail below in conjunction with specific embodiments.

[0058] All reactions were carried out under positive argon pressure in flame-dried modified Schlenk flasks equipped with glass stoppers or rubber septa. The progress of the reactions was followed by thin layer chromatography (TLC) and detected by fluorescence and / or acid ceric ammonium molybdate staining.

[0059] Example 1

[0060] 1 In Example 1, 1A-1B, 1D-1F, 1J, 2A, 2F, 3A, 3F, 4A, 4E, 4F, 5A, and 5F were prepared according to the following procedure:

[0061]

[0062] The glycosylation reaction of the acceptor, which is a monohydroxy compound soluble in toluene, was carried out using the standard operating procedure (1): Under an inert gas atmosphere, the acceptor (1.0 equivalent) was added to a solution of the glycoene donor (1.2 equivalent) and dry MS (100 mg / ml) in anhydrous Toluene solution (0.1M), stirred at 0 ° C for 5 min, and then added mercuric trifluoromethanesulfonate (0.1 equivalent). The reaction was detected by TLC plate until completion, Et3N was added to quench the reaction, diluted with DCM, and the precipitate was filtered out through a diatomaceous earth pad. The organic layer was washed with NaHCO3 (aq.) and NaCl (aq.), dried with Na2SO4, filtered and the solvent was removed under reduced pressure distillation. The resulting residue was purified by silica gel column chromatography to obtain the corresponding 2-deoxyglycosylation product.

[0063] 1.1 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 1Aα

[0064] The standard procedure (1) was used: 1 (50.0 mg, 120 μmol) was glycosylated with A (46.5 mg, 100 μmol) to give 1Aα (84.3 mg, 95%) as a colorless oil. 1H NMR (400MHz, CDCl3) δ7.45–7.17(m,35H,ArH),5.02(d,J=3.3Hz,1H,1'-H),4.98(d,J=10.7Hz,1H,OCH2Ph),4.91(d,J=11.6Hz,1H,OCH2Ph),4.86–4.76(m ,3H,OCH2Ph),4.68(d,J=12.2Hz,1H,OCH2Ph),4.63–4.55(m,4H,1-H,OCH2Ph),4.52(d,J=10.8Hz,1H,OCH2Ph),,4.41(d,J=11.7Hz,1H,OCH2Ph),4.33(d, J=11.8Hz,1H,OCH2Ph),3.98(t,J=9.2Hz,1H,3-H),3.84(dt,J=26.4,5.8Hz, 4H,3'-H,4'-H,5'-H,6a-H),3.72(dd,J=10.3,4.4Hz,1H,5-H),3.61(d,J=11 .3Hz,1H,6b-H),3.57–3.42(m,4H,6a'-H,2-H,6b'-H,4-H),3.31(s,3H,OCH3 ), 2.20 (td, J=12.6, 3.7Hz, 1H, 2a'-H), 2.01 (dd, J=12.5, 4.3Hz, 1H, 2b'-H). For example Figure 1 shown.

[0065] 1.2 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 1Bα

[0066] The standard procedure (1) was used: 1 (30.0 mg, 72 μmol) was glycosylated with B (30.4 mg, 60 μmol) to give 1Bα (49.8 mg, 90%) as a white solid. 1H NMR (400MHz, CDCl3) δ8.01–7.96(m,2H,ArH),7.95–7.89(m,2H,ArH),7.90–7.82( m,2H,ArH),7.54–7.15(m,24H,ArH),6.12(t,J=9.9Hz,1H,3-H),5.64(t,J=9.9Hz ,1H,4-H),5.28(dd,J=10.2,3.7Hz,1H,2-H),5.20(d,J=3.6Hz,1H,1-H),5.00(d, J=3.3Hz,1H,1'-H),4.89(d,J=11.6Hz,1H,OCH2Ph),4.57(d,J=12.6Hz,3H,OCH2P h),4.32(d,J=12.0Hz,1H,OCH2Ph),4.23(d,J=12.0Hz,1H,OCH2Ph),4.19(dd,J=8 .8,5.0Hz,1H,5-H),3.95(ddd,J=12.0,4.6,2.4Hz,1H,3'-H),3.85(m,3H,4'-H,5 '-H,6a-H),3.58(dd,J=11.1,3.0Hz,1H,6b-H),3.46–3.36(m,5H,6a'-H,6b'-H,O CH3), 2.18 (td, J=12.4, 3.7Hz, 1H, 2a'-H), 1.98 (dd, J=12.7, 4.6Hz, 1H, 2b'-H). Such as Figure 2 shown.

[0067] 1.3 The receptor is the 2-deoxyglycosylation product 1Dα of the monohydroxy compound

[0068] The standard procedure (1) was used: 1 (30.0 mg, 72 μmol) was glycosylated with D (35.9 mg, 60 μmol) to give 1Dα (41.8 mg, 78%) as a white solid. 1 H NMR (400MHz, CDCl3) δ7.92–7.87(m,2H,ArH),7.87–7.82(m,2H,ArH),7.80–7.74(m,2H,ArH),7.47–7.11(m,24H,ArH),6.91–

[0069] 6.80(m,2H,ArH),6.70–6.59(m,2H,ArH),5.84(t,J=9.7Hz,1H,3-H),5.65(dd,J=9.8,7.8Hz,1H,2-H),5.57(t,J=9.7Hz,1H,4-H),5.15(d,J=7.9Hz,1H,1-H),4.91(d,J=3.3Hz,1H,1’-H),4.80(d,J=11.6Hz,1H,OCH2Ph),4.48(d,J=11.6Hz,1H,OCH2Ph),4.42(s,2H,OCH2Ph),4.28(d,J=12.0Hz,1H,OCH2Ph),4.21(d,J=11.9Hz,1H,OCH2Ph),3.99(ddd,J=9.3,5.2,3.3Hz,1H,5-H),3.83(dd,J=11.0,5.3Hz,1H,6a-H),3.80–3.73(m,2H,3’-H,5’-H),3.70(s,1H,4’-H),3.60(s,4H,6b-H,OCH3),3.37(qt,J=9.4,4.9Hz,2H,6a’-H,6b’-H),2.08(td,J=12.4,3.7Hz,1H,2a’-H),1.87(dd,J=12.7,4.6Hz,1H,2b’-H). 13CNMR(100MHz, CDCl3)δ165.86(CO(×2)),165.16(C=O),155.73(CO),151.05( CO),138.89(4℃),138.62(4℃),138.26(4℃),133.41(4℃),133.28(4℃),133.25 (4℃),129.82(CH),129.80(CH),129.29(CH),129.06(CH),128.91(CH),128.4 6(CH),128.41(CH),128.39(CH),128.32(CH),128.19(CH),128.17(CH),127. 55(CH),127.49(CH),127.45(CH),127.36(CH),118.98(CH),114.50(CH),10 0.76(C-1),98.21(C-1'),74.85(C-3'),74.27(CH2Ph),73.21(CH2Ph),73.14 (C-4),73.13(C-5),73.10(C-3),71.87(C-2),70.56(CH2Ph),69.86(C-4),69 .81(C-5'),69.50(C-6'),66.20(C-6),55.57(OCH3),30.83(C-2').ESI-HRMS Calcd forC 61 H 62 NO 14 [M+NH4] + :1032.4165,found:1032.4188. Figure 4 shown.

[0070] 1.4 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 1Eα

[0071] The standard procedure (1) was used: 1 (30.0 mg, 72 μmol) was glycosylated with E (27.9 mg, 60 μmol) to give 1Eα (46.9 mg, 89%) as a colorless oil. 1H NMR (400MHz, CDCl3) δ7.44–7.17(m,30H,ArH),5.47(d,J=3.7Hz,1H,1'-H),5.00(d,J=10.9Hz,1H,OCH2Ph),4.88(d,J=11.6Hz,1H,O CH2Ph),4.74(d,J=12.1Hz,1H,OCH2Ph),4.68–4.56(m,4H,OCH2Ph,1-H),4.56–4.46(m,3H,OCH2Ph),4.40–4.33(m,2H,OCH2Ph),4.30 (d,J=11.7Hz,1H,OCH2Ph),3.92–3.75(m,4H,3-H,3'-H,4'-H,5'-H),3.75–3.58(m,4H,4-H,5-H,6-H),3.51(dd,J=9.7,3.5Hz,1H,2 -H),3.49–3.43(m,2H,6a'-H,6b'-H),3.39(s,3H,OCH3),2.13(td,J=12.4,3.9Hz,1H,2a'-H),1.87(dd,J=12.6,4.5Hz,1H,2b'-H). Such as Figure 5 shown.

[0072] 1.5 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 1Fα

[0073] The standard procedure (1) was used: 1 (30.0 mg, 72 μmol) was glycosylated with F (22.4 mg, 60 μmol) to give 1Fα (42.4 mg, 90%) as a white solid. 1H NMR (400MHz, CDCl3) δ7.40(dd,J=6.6,3.0Hz,2H,ArH),7.35–7.23(m,25H,ArH),5.53(d,J=3.5Hz,1H,1'-H),5.49(s,1H,PhCHO2),4.89(d,J=11.5Hz,1H ,OCH2Ph),4.70(d,J=12.2Hz,1H,OCH2Ph),4.61(d,J=11.5Hz,1H,OCH2Ph),4.59–4.47(m,4H,OCH2Ph,1-H),4.42(d,J=11.7Hz,1H,OCH2Ph),4.37(d,J=11 .7Hz,1H,OCH2Ph),4.31–4.19(m,3H,3-H,5'-H,6a-H),3.95–3.88(m,2H,3' -H,4'-H),3.79(dd,J=10.0,4.7Hz,1H,5-H),3.70–3.59(m,3H,6b-H,6a'-H, 6b'-H),3.54(t,J=9.4Hz,1H,4-H),3.43(dd,J=9.5,3.7Hz,1H,2-H),3.32(s ,3H,OCH3),2.20(td,J=12.2,3.7Hz,1H,2a'-H),2.06–1.99(m,1H,2b'-H). Such as Figure 6 shown.

[0074] 1.6 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 1Jα

[0075] The standard procedure (1) was used: 1 (30.0 mg, 72 μmol) was glycosylated with J (24.9 mg, 60 μmol) to give 1Jα (47.0 mg, 81%) as a white solid. 11H NMR (400 MHz, CDCl3) δ 7.30–7.15 (m, 23H, ArH), 5.18 (d, J = 5.0 Hz, 1H, 6’-H), 5.07 (d, J = 3.5 Hz, 1H, 1-H), 4.86 (d, J = 11.6 Hz, 1H, OCH2Ph), 4.55 (d, J = 8.5 Hz, 3H, OCH2Ph), 4.43 (d, J = 11.7 Hz, 1H, OCH2Ph), 4.38–4.31 (m, 2H, OCH2Ph, 16’-H), 3.98–3.80 (m, 3H, 3-H, 4-H, 5-H), 3.58–3.46 (m, 2H, 6a-H, 6b-H), 3.42–3.26 (m, 3H, 3’-H, 26a’-H, 26b’-H), 2.24–2.17 (m, 2H, CH2), 2.14 (dd, J = 12.0, 3.7 Hz, 1H, 2a-H), 1.95–1.84 (m, 2H, CH2, 2b-H), 1.79 (m, 2H, CH, CH2), 1.69 (m, J = 19.8, 13.1, 3.8 Hz, 2H, CH, CH2), 1.62–1.50 (m, 3H, CH, CH2), 1.49 (s, 1H), 1.47–1.30 (m, 3H, CH2), 1.28–1.16 (m, 2H, CH2), 1.15–0.97 (m, 2H, CH, CH2), 0.94 (s, 3H, CH3), 0.90 (d, J = 6.9 Hz, 3H, CH3), 0.84 (dd, J = 11.3, 5.3 Hz, 1H, CH), 0.72 (t, J = 3.2 Hz, 6H, CH3). As Fig.10 shown. 13C NMR(100MHz, CDCl3)δ139.93(C-5'),137.98,(4℃)137.65(4℃),137.18(4℃),127.35( CH),127.32(CH),127.15(CH),127.12(CH),126.70(CH),126.57(CH),126.43(CH),1 26.40(CH),126.27(CH),120.30(C-6'),108.24(C-22'),94.69(C-1),79.81(C-16') ,75.04(C-3'),74.06(C-3),73.25(CH2Ph),72.41(CH2Ph),72.22(C-4),69.47(CH2Ph ),68.89(C-5),68.70(C-6),65.83(C-26'),61.13(C-17'),55.52(CH),49.03(CH),4 0.61(CH),39.27(CH2),39.00(CH2),38.78(CH2),36.07(CH2),35.85(CH2),31.08(C H2),30.85(C-2),30.68(CH2),30.45(CH2),30.40(CH2),29.30(CH),27.81(CH2),26 .80(CH2),19.83(CH2),18.37(CH3),16.12(CH3),15.26(CH3),13.50(CH3).ESI-HRMS Calcd for C 54 H 70 NaO7[M+Na] + :853.5014,found:853.5029.

[0076] 1.7 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 2Aα

[0077] The standard procedure (1) was used: 2 (100.0 mg, 0.18 mmol) was glycosylated with A (68.5 mg, 0.15 mmol) to give 2Aα (140.0 mg, 89%) as a white foam. 1 H NMR (400MHz, CDCl3) δ7.60 (d, J=7.2Hz, 4H, ArH), 7.42–7.17 (m, 31H, ArH), 5.02–4.88 (m, 3H, 1'-H, OCH2Ph), 4.85–

[0078] 4.74 (m, 3H, OCH2Ph), 4.67 (d, J = 12.1 Hz, 1H, OCH2Ph), 4.63–4.54 (m, 4H, 1-H, OCH2Ph), 4.51 (d, J = 11.0 Hz, 1H, OCH2Ph), 3.98 (t, J = 9.2 Hz, 1H, 3-H), 3.93–3.83 (m, 2H, 3’-H, 4’-H), 3.78 (q, J = 5.5, 4.6 Hz, 1H, 5’-H), 3.75–3.63 (m, 4H, 5-H, 6a-H, 6a’-H, 6b’-H), 3.58 (d, J =

[0079] 10.0 Hz, 1H, 6b-H), 3.50 (dd, J = 9.6, 3.6 Hz, 1H, 2-H), 3.39 (t, J = 9.3 Hz, 1H, 4-H), 3.29 (s, 3H, OCH3), 2.16 (td, J = 12.2, 3.6 Hz, 1H, 2a’-H), 1.97 (dd, J = 12.6, 4.4 Hz, 1H, 2b’-H), 1.02 (s, 9H, SiPh2C(CH3)3). As Fig.11 shown. 13 C NMR (100 MHz, CDCl3) δ 138.94 (4 °C), 138.76 (4 °C), 138.50 (4 °C), 138.24 (4 °C), 138.18 (4 °C), 135.58 (CH), 135.55 (CH), 133.53 (4 °C), 133.44 (4 °C), 129.66 (CH), 129.64 (CH), 128.48 (CH), 128.43 (CH), 128.14 (CH), 128.07 (CH), 128.04 (CH), 127.93 (CH), 127.70 (CH), 127.65 (CH), 127.60 (CH), 127.40 (CH), 127.36 (CH), 97.94 (C-1), 97.77 (C-1’), 82.15 (C-3), 80.08 (C-2), 78.27 (C-4), 75.87 (CH2Ph), 75.06 (CH2Ph), 74.42 (C-3’), 74.30 (CH2Ph), 73.30 (CH2Ph), 73.00 (C-4’), 71.74 (C-5’), 70.22 (CH2Ph), 70.10 (C-5), 65.69 (C-6), 63.23 (C-6’), 54.92 (OCH3), 31.07 (C-2’), 26.89 (SiPh2C(CH3)(CH3)(CH3)), 19.24 (SiPh2C(CH3)3). ESI-HRMS Calcd for C64 H 72 NaO 10 Si[M+Na] + :1051.4787,found:1051.4807.

[0080] 1.8 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 2Fα

[0081] The standard procedure (1) was used: 2 (55.0 mg, 97 μmol) was glycosylated with F (30.2 mg, 81 μmol) to give 2Fα (47.0 mg, 82%) as a white solid. 1 H NMR (400MHz, CDCl3) δ7.67–7.55(m,4H,ArH),7.36–7.10(m,25H,ArH),5.43(d,J =3.2Hz,1H,1'-H),5.40(s,1H,PhCHO2),4.86(d,J=11.3Hz,1H,OCH2Ph),4.56(dd ,J=11.9,4.6Hz,2H,OCH2Ph),4.49(s,2H,OCH2Ph),4.45–4.37(m,2H,OCH2Ph,1- H),4.21(q,J=9.4,8.1Hz,2H,3-H,5'-H)4.12(dd,J=10.0,4.6Hz,1H,6a-H),3.95 (s,1H,4'-H),3.91–3.81(m,1H,3'-H),3.75(d,J=6.9Hz,2H,6a'-H,6b'-H),3.6 7(dd,J=9.8,4.5Hz,1H,5-H),3.58(t,J=10.2Hz,1H,6b-H),3.45(t,J=9.3Hz,1H, 4-H),3.34(dd,J=9.5,3.6Hz,1H,2-H),3.23(s,3H,OCH3),2.09(td,J=12.3,3.6H z,1H,2a'-H),1.94(dd,J=12.7,4.4Hz,1H,2b'-H),0.98(s,9H,SiPh2C(CH3)3). Such as Fig.12 shown. 13C NMR (100MHz, CDCl3) δ139.11 (4℃), 138.78 (4℃), 138.38 (4℃), 137.29 (4℃), 135.6 9(4℃),135.64(4℃),133.74(CH),133.50(CH),129.56(CH),129.46(CH),128.96( CH),128.43(CH),128.26(CH),128.15(CH),128.13(CH),128.06(CH),127.93(CH ),127.74(CH),127.71(CH),127.67(CH),127.53(CH),127.38(CH),127.28(CH), 126.04(CH),101.34(PhCHO2),99.14(C-1),97.55(C-1'),83.28(C-4),78.51(C- 2),74.67(CH2Ph),74.58(C-3'),73.44(CH2Ph),73.37(C-4'),71.72(C-3),71.2 4(C-5'),70.20(CH2Ph),69.17(C-6),62.66(C-6'),61.93(C-5),55.17(OCH3),3 1.19(C-2'),26.96(SiPh2C(CH3)(CH3)(CH3)),19.27(SiPh2C(CH3)3).ESI-HRMS Calcd for C 57 H 64 NaO 10 Si[M+Na] + :959.4161,found:959.4189.

[0082] 1.9 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 3Aα

[0083] The standard procedure (1) was used: 3 (45.0 mg, 92 μmol) was glycosylated with A (35.6 mg, 77 μmol) to give 3Aα (71.0 mg, 96%) as a colorless oil. 1H NMR(400MHz,CDCl3)δ7.25(m,15H,ArH),4.90(d,J=10.8Hz,2H,1'-H,OCH2Ph),4.82–4.69(m,3H,OCH2Ph),4.60(d,J=12.1Hz,1H,OCH2Ph),4.54 (d,J=10.8Hz,1H,OCH2Ph),4.51(d,J=3.6Hz,1H,1-H),4.00–3.94(m,1H,3'-H),3.91(d,J=9.3Hz,1H,2-H),3.73(d,J=2.2Hz,1H,4'-H),3.72–3. 64(m,2H,3-H,6a'-H),3.59(m,4H,5'-H,6a-H,6b-H,6b'-H),3.42(dd,J =9.6,3.6Hz,1H,4-H),3.34(t,J=8.9Hz,1H,5-H),3.28(s,3H,OCH3),2. 01(td,J=13.3,12.7,4.1Hz,1H,2a'-H),1.58(dd,J=12.4,4.3Hz,1H,2b'-H),0.90–0.76(m,24H,3×SiC(CH3)3),0.05–-0.09(m,18H,6xSiCH3). Such as Fig.13 shown.

[0084] 1.10 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 3Fα

[0085] The standard procedure (1) was used: 3 (45.0 mg, 92 μmol) was glycosylated with F (28.6 mg, 77 μmol) to give 3Fα (58.2 mg, 88%) as a colorless oil. 11H NMR (400 MHz, CDCl3) δ 7.43–7.19 (m, 10H, ArH), 5.40 (s, 1H, PhCHO2), 5.29 (d, J = 3.3 Hz, 1H, 1’-H), 4.74 (d, J = 12.6 Hz, 1H, OCH2Ph), 4.46 (d, J = 12.6 Hz, 1H, OCH2Ph), 4.32 (d, J = 3.6 Hz, 1H, 1-H), 4.21 (t, J = 9.4 Hz, 1H, 3-H), 4.12 (dd, J = 10.1, 4.8 Hz, 1H, H-6a), 4.03 (ddd, J = 11.8, 4.4, 2.4 Hz, 1H, 3’-H), 3.93 (t, J = 6.8 Hz, 1H, 5’-H), 3.77 (d, J = 2.1 Hz, 1H, 4’-H), 3.69 (td, J = 9.9, 4.7 Hz, 1H, 5-H), 3.62–3.53 (m, 3H, H-6b, H-6a’, H-6b’), 3.43 (t, J = 9.4 Hz, 1H, 4-H), 3.29 (dd, J = 9.5, 3.7 Hz, 1H, 2-H), 3.23 (s, 3H, OCH3), 1.98 (td, J = 12.2, 3.6 Hz, 1H, 2a’-H), 1.56 (dd, J = 12.5, 4.3 Hz, 1H, 2b’-H), 0.89–0.78 (m, 29H, 3×SiC(CH3)3), 0.08– -0.08 (m, 21H, 6x SiCH3). As Fig.14 shown 13C NMR(100MHz, CDCl3)δ137.55(4℃),136.38(4℃),127.89(CH),127.42(CH),127 .19(CH),126.88(CH),126.83(CH),125.16(CH),100.48(PhCHO2),98.43(C-1) ,96.69(C-1'),82.46(C-4),77.32(C-2),72.54(CH2Ph),71.20(C-5'),70.74 (C-3),69.10(C-4'),68.15(C-6),67.41(C-3'),61.06(C-6'),60.99(C-5),54 .28(OCH3),32.65(C-2'),25.23(SiC(CH3)(CH3)(CH3)),25.21(SiC(CH3)(CH3)(CH3)),24.91(SiC(CH3)(CH3)(CH3)),17.61(SiC(CH3)3),17.53(SiC(CH3) 3), 17.23(SiC(CH3)3), 0.00(Si(CH3)2), -4.95(Si(CH3)2), -5.31(Si(CH3)2), -5.64(Si(CH3)2), -5.89(Si(CH3)2), -6.34(Si(CH3)2), -6.42(Si(CH3)2).

[0086] 1.11 receptor is the 2-deoxyglycosylation product of the monohydroxy compound 4Aα

[0087] The standard procedure (1) was used: 4 (30.0 mg, 48 μmol) was glycosylated with A (18.5 mg, 40 μmol) to give 4Aα (39.3 mg, 90%) as a colorless oil. 11H NMR (400 MHz, CDCl3) δ 7.70–7.65 (m, 4H, ArH), 7.42–7.21 (m, 22H, ArH), 5.00–4.93 (m, 2H, 1’-H), 4.88 (d, J = 11.0 Hz, 1H, OCH2Ph), 4.84–4.75 (m, 2H, OCH2Ph), 4.66 (d, J = 12.1 Hz, 1H, OCH2Ph), 4.63–4.58 (m, 2H, OCH2Ph, 1-H), 4.09–4.02 (m, 1H, 3’-H), 3.98 (t, J = 9.3 Hz, 1H, 3-H), 3.91 (dd, J = 10.8, 1.9 Hz, 1H, 6a’-H), 3.83 (dd, J = 11.2, 5.3 Hz, 1H, 6a-H), 3.75 (dq, J = 8.5, 2.8, 2.2 Hz, 2H, 5-H, 6b’-H), 3.70–3.65 (m, 1H, 5’-H), 3.64–3.59 (m, 1H, 6b-H), 3.52–3.41 (m, 3H, 2-H, 4-H, 4’-H), 3.37 (s, 3H, OCH3), 2.12 (dd, J = 13.2, 5.3 Hz, 1H, 2a’-H), 1.67 (ddd, J = 13.2, 11.3, 3.6 Hz, 1H, 2b’-H), 1.13–0.81 (m, 45H, 4×Si(CH(CH3)2), SiPh2C(CH3)3). As Fig.15 shown. 13C NMR(100MHz, CDCl3)δ138.76(4℃),138.30(4℃),138.19(4℃),135.81(CH),135.64(CH),134.07(4℃),133.71(4℃),129.43(CH),129.41(CH),1 28.45(CH),128.39(CH),128.38(CH),128.07(CH),127.98(CH),127.89(CH),127.62(CH),127.60(CH),127.55(CH),127.48(CH),127.44(CH) ,97.83(C-1),97.16(C-1'),82.26(C-3),80.06(C-2),78.25(C-4),75.78(CH2Ph),75.06(CH2Ph),74.57(C-4'),73.32(CH2Ph),73.21(C-5' ),71.83(C-3'),70.17(C-5),65.19(C-6),63.72(C-6'),54.83(OCH3),38.06(C-2'),26.84(SiC(CH3)(CH3)(CH3))19.32(SiC(CH3)3),17.65

[0088] (Si(CH(CH3)(CH3)),17.40(2×Si(CH(CH3)(CH3)),17.37(Si(CH(CH3)(CH3)),17.33

[0089] (Si(CH(CH3)(CH3)),17.28(Si(CH(CH3)(CH3)),17.27(Si(CH(CH3)(CH3)),17.23

[0090] (Si(CH(CH3)(CH3)),12.93(2×Si(CH(CH3)2)2),12.42(Si(CH(CH3)2)2),12.20(Si(CH(CH3)2)2).ESI-HRMS Calcd for C 62 H 86 O 11 KSi3[M+K] + :1113.5371,found:1113.5302.

[0091] 1.12 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 4Eα

[0092] The standard procedure (1) was used: 4 (50.0 mg, 80 μmol) was glycosylated with E (30.8 mg, 66 μmol) to give 4Eα (57.8 mg, 79%) as a colorless oil. 1 H NMR (400MHz, CDCl3) δ7.67–7.53(m,4H,ArH),7.39–7.15(m,17H,ArH),7.13–6.98(m,5H,ArH),5.22(d,J=3.4Hz,1H,1'-H),4.96(d,J=10.9Hz,1H,OC H2Ph),4.73–4.50(m,4H,OCH2Ph,1-H),4.39(d,J=12.3Hz,1H,OCH2Ph),4.11(d,J=12.2Hz,1H,OCH2Ph),3.93–3.76(m,2H,3'-H,3-H),3.75–3.59(m,2 H,5-H,6a'-H),3.59–3.49(m,3H,4'-H,6b'-H,6a-H),3.45(ddd,J=10.1,6 .4,3.0Hz,3H,2-H,4-H,6b-H),3.40–3.35(m,1H,5'-H),3.33(s,3H,OCH3), 1.95(dd,J=13.2,5.2Hz,1H,2a'-H),1.60–1.47(m,1H,2b'-H),1.15–0.73(m,48H,4×Si(CH(CH3)2),SiPh2C(CH3)3).),0.86(dd,J=6.0,2.8Hz,4H). Such as Fig.16 shown. 13C NMR (100MHz, CDCl3) δ137.53 (4℃), 137.23 (4℃), 137.02 (4℃), 134.98 (CH), 134.60 (CH), 133.13 (4℃ ),132.47(4℃),128.39(CH),128.35(CH),127.44(CH),127.39(CH),127.16(CH),127.11(CH),126. 91(CH),126.68(CH),126.56(CH),126.44(CH),126.40(CH),126.26(CH),126.07(CH),98.43(C-1 '),96.60(C-1),80.94(C-3),79.06(C-2),75.87(C-4),74.44(CH2Ph),72.98(C-4'),72.76(C-5') ,72.16(CH2Ph),72.01(CH2Ph),70.48(C-3'),68.90(C-6),68.80(C-5),61.87(C-6'),54.18(OCH 3),37.70(C-2'),25.88(SiC(CH3)(CH3)(CH3)),18.31(SiC(CH3)3),16.64(Si(CH(CH3)(CH3)),16 .45(Si(CH(CH3)(CH3)),16.43(2×Si(CH(CH3)(CH3)),16.37(Si(CH(CH3)(CH3)),16.35(Si(CH(CH 3)(CH3)),16.33(Si(CH(CH3)(CH3)),16.29(2×Si(CH(CH3)(CH3)),11.98(Si(CH(CH3)2)2),11.89

[0093] (Si(CH(CH3)2)2),11.44(Si(CH(CH3)2)2),11.29(Si(CH(CH3)2)2).ESI-HRMS Calcdfor C 62 H 92 O 11 NSi3[M+NH4] + :1108.5817,found:1108.5830.

[0094] 1.13 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 4Fα

[0095] The standard procedure (1) was used: 4 (45.0 mg, 72 μmol) was glycosylated with F (22.3 mg, 60 μmol) to give 4Fα (45.0 mg, 75%) as a colorless oil. 1 H NMR (400MHz, CDCl3) δ7.77–7.68(m,5H,ArH),7.51–7.46(m,2H,ArH),7.41–7.22(m,17H,ArH),5.52(s,1H,PhCHO2),5.49(d,J=3.5Hz,1H,1-H'),4. 82(d,J=12.5Hz,1H),4.54(d,J=12.4Hz,1H),4.42(d,J=3.8Hz,1H,1-H), 4.30–4.21(m,2H,3-H,6a-H),4.14(ddd,J=12.6,8.1,5.1Hz,1H,3'-H),3. 87(dd,J=10.8,6.1Hz,3H,5'-H,6a'-H,6b'-H),3.77(m,2H,4'-H,5-H),3 .68(t,J=10.2Hz,1H,6b-H),3.58(t,J=9.3Hz,1H,4-H),3.39(dd,J=9.5,3 .7Hz,1H,2-H),3.29(s,3H),2.12(dd,J=13.3,5.3Hz,1H,2a'-H),1.70–1.61(m,2H,2b'-H),1.13–0.83(m,47H,4×Si(CH(CH3)2),SiPh2C(CH3)3). Such as Fig.17 shown. 13C NMR(100MHz, CDCl3)δ138.27(4℃),137.43(4℃),136.15(CH),135.80(CH),13 4.48(4℃),133.86(4℃),129.23(CH),128.98(CH),128.47(CH),128.30(CH), 128.05(CH),127.90(CH),127.39(CH),127.31(CH),126.03(CH),101.26(Ph CHO2),99.41(C-1),96.47(C-1'),83.41(C-4),77.52(C-2),73.93(C-4'),72 .61(C-5'),71.88(C-3'),71.76(C-3),69.18(C-6),62.95(C-6'),61.94(C- 5),55.18(CH2Ph),38.13(C-2'),26.99(SiC(CH3)(CH3)(CH3)),19.45(SiC(C H3)3),17.84(Si(CH(CH3)(CH3)),17.53(Si(CH(CH3)(CH3)),17.51(Si(CH(CH3)(CH3)),17.47(Si(CH(CH3)(CH3)),17.37(Si(CH(CH3)(CH3)),17.30(2×

[0096] Si(CH(CH3)(CH3)),13.09(Si(CH(CH3)2)2),13.06(Si(CH(CH3)2)2),12.49(Si(CH(CH3)2)2),12.20(Si(CH(CH3)2)2).ESI-HRMS Calcd for C 55 H 82 O 11 NSi3[M+NH4] + :1016.5191,found:1016.5208.

[0098] 1.14 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 5Aα

[0099] The standard procedure (1) was used: 5 (15.0 mg, 48 μmol) was glycosylated with A (18.5 mg, 40 μmol) to give 5Aα (28.6 mg, 92%) as a white solid. 11H NMR (400 MHz, CDCl3) δ 7.44–7.21 (m, 25H, ArH), 4.97 (dd, J = 14.4, 11.2 Hz, 2H, OCH2Ph), 4.83 (ddd, J = 20.4, 14.3, 10.2 Hz, 4H, OCH2Ph, 1’-H), 4.68 (dd, J = 11.9, 2.7 Hz, 2H, OCH2Ph), 4.58 (d, J = 3.1 Hz, 3H, OCH2Ph, 1-H), 4.53 (d, J = 10.9 Hz, 1H, OCH2Ph), 3.98 (t, J = 9.2 Hz, 1H, 3-H), 3.88 (ddd, J = 12.1, 4.6, 2.4 Hz, 1H, 3’-H), 3.83–3.77 (m, 2H, 6a-H, 5’-H), 3.69 (dd, J = 10.4, 5.2 Hz, 1H, 5-H), 3.58 (s, 1H, 4’-H), 3.54–3.41 (m, 3H, 2-H, 4-H, 6b-H), 3.31 (s, 3H, OCH3), 2.14 (td, J = 12.4, 3.7 Hz, 1H, 2a’-H), 1.91 (dd, J = 12.5, 4.6 Hz, 1H, 2b’-H), 1.12 (d, J = 6.5 Hz, 3H, 6’-CH3). As Fig.19 shown. 13 13C NMR (100 MHz, CDCl3) δ 138.89 (4 °C), 138.70 (4 °C), 138.56 (4 °C), 138.19 (4 °C), 138.16 (4 °C), 128.50 (CH), 128.48 (CH), 128.42 (CH), 128.40 (CH), 128.20 (CH), 128.10 (CH), 128.07 (CH), 127.95 (CH), 127.87 (CH), 127.72 (CH), 127.56 (CH), 127.52 (CH), 127.36 (CH), 98.13 (C-1’), 97.88 (C-1), 82.20 (C-3), 80.02 (C-2), 77.92 (C-4), 75.86 (CH2Ph), 75.64 (C-4’), 75.09 (CH2Ph), 74.86 (C-3’), 74.38 (CH2Ph), 73.36 (CH2Ph), 70.28 (C-5), 70.09 (CH2Ph), 66.69 (C-5’), 66.05 (C-6), 55.01 (OCH3), 30.65 (C-2’), 17.29 (C-6’). ESI-HRMS Calcd for C 48 H 54 KO9 [M+K] +:813.3400,found:813.3401.

[0100] 1.15 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 5Fα

[0101] The standard procedure (1) was used: 5 (15.0 mg, 48 μmol) was glycosylated with F (14.8 mg, 40 μmol) to give 5Fα (28.6 mg, 77%) as a white solid. 1 H NMR (400MHz, CDCl3) δ7.36(dd,J=6.8,3.0Hz,2H,ArH),7.30–7.14(m,18H,ArH),5.38(s,1H,PhCHO2),5.29(d,J=3.6Hz,1H,1'-H),4.81(d,J =11.8Hz,1H,OCH2Ph),4.63–4.52(m,4H,OCH2Ph,1-H),4.50(s,2H,OCH2Ph),4.16(dd,J=10.2,4.8Hz,1H,6a-H),4.10(t,J=9.4Hz,1H,3-H), 3.93(q,J=6.4Hz,1H,5'-H),3.84–3.71(m,2H,3'-H,5-H),3.60(t,J=10.3Hz,1H,6b-H),3.43(dd,J=9.3,3.6Hz,1H,2-H),3.37(d,J=9.5Hz, 2H,4'-H,4-H),3.31(s,3H,OCH3),2.07(td,J=12.4,3.8Hz,1H,2a'-H),1.83(dd,J=12.6,4.6Hz,1H,2b'-H),0.72(d,J=6.4Hz,3H,6'-CH3). Such as Fig. 20 shown.

[0102] 13C NMR(100MHz, CDCl3)δ139.07(4℃),138.87(4℃),137.87(4℃),137.45(4℃),129.05(CH),128.52(CH),128.39(CH),128.36(CH ),128.23(CH),128.17(CH),128.12(CH),128.09(CH),128.00(CH),127.41(CH),127.35(CH),127.17(CH),126.31(CH),101. 93(PhCHO2),98.68(C-1'),98.51(C-1),80.79(C-2),80.38(C-4),76.06(C-4'),75.53(C-3'),74.31(CH2Ph),73.35(C-3), 73.12(CH2Ph),70.28(CH2Ph),69.16(C-6),66.61(C-5'),62.54(C-5),55.29(OCH3),30.79(C-2').,16.90(C-6').ESI-HRMS Calcd for C 41 H 46 NaO9[M+Na] + :705.3035,found:705.3004.

[0103] Example 2: In Example 2, 1C, 1G, 1H, 1I, and 4G were prepared according to the following procedure:

[0104]

[0105] The glycosylation reaction of the acceptor, which is a monohydroxy compound that is poorly soluble in toluene, was carried out using the standard operating procedure (2): Under an inert gas atmosphere, the acceptor (1.0 equivalent) was added to a solution of the glycoene donor (1.2 equivalent) and dry MS (100 mg / ml) in anhydrous Toluene / DCM = 3 / 1 solution (0.1M), 0 ° C stirring 5min, then add trifluoromethanesulfonic acid mercuric acid (0.1 equivalent) thereto. TLC plate detection until the reaction is complete, add Et3N quench the reaction, dilute with DCM, filter out the precipitate through a diatomaceous earth pad. The organic layer is washed with NaHCO3 (aq.) and NaCl (aq.), and dried with Na2SO4, filtered and the solvent is removed under reduced pressure distillation. The resulting residue is purified by silica gel column chromatography to obtain the corresponding 2-deoxyglycosylation product.

[0106] 2.1 The acceptor is the 2-deoxyglycosylation product 1Cα of the monohydroxy compound

[0107] The standard procedure (2) was used: 1 (30.0 mg, 72 μmol) was glycosylated with C (33.4 mg, 60 μmol) to give 1Cα (43.4 mg, 85%) as a white solid. 1 H NMR (400MHz, CDCl3) δ7.40–7.19(m,30H,ArH),7.02–6.97(m,2H,ArH),6.80–6.75(m,2H,ArH),5.05(d,J=11.1Hz,2H,O CH2Ph,1'-H),4.96(d,J=10.9Hz,1H,OCH2Ph),4.93–4.85(m,2H,OCH2Ph,1-H),4.82(dd,J=10.9,6.4Hz,3H,OCH2Ph),4. 59(d,J=10.1Hz,3H,OCH2Ph),4.53(d,J=10.9Hz,1H,OCH2Ph),4.42(d,J=11.9Hz,1H,OCH2Ph),4.36(d,J=11.9Hz,1H,OC H2Ph),3.93–3.83(m,2H,3'-H,5'-H),3.82–3.76(m,2H,4'-H,6a-H),3.70(d,J=9.1Hz,6H,2-H,3-H,6b-H,OCH3),3.57–

[0108] 3.47(m,4H,4-H,5-H,6a'-H,6b'-H),2.20(td,J=12.3,3.6Hz,1H,2a'-H),2.04(dd,J=12.6,4.5Hz,1H,2b'-H). Such as Figure 3 shown. 13C NMR(100MHz, CDCl3)δ154.32(CO),150.35(CO),137.88(4℃),137.48(4℃),13 7.43(4℃),137.26(4℃),137.24(4℃),136.97(4℃),127.42(CH),127.38(CH),1 27.26(CH),127.18(CH),127.14(CH),126.85(CH),126.80(CH),126.75(CH), 126.65(CH),126.61(CH),126.52(CH),126.48(CH),126.41(CH),126.30(CH) ,117.49(CH),113.47(CH),101.63(C-1),97.10(C-1'),83.68(C-3),81.08(C -2),77.04(C-4),74.75(CH2Ph),74.03(CH2Ph),73.96(CH2Ph),73.60(C-3') ,73.45(C-5),73.26(CH2Ph),72.08(C-4'),72.07(CH2Ph),69.35(CH2Ph),68 .71(C-5'),68.43(C-6'),64.87(C-6),54.55(OCH3),29.94(C-2').ESI-HRMS Calcd for C 61 H 68 NO 11 [M+NH4] + :990.4787,found:990.4786.

[0109] 2.2 The receptor is the 2-deoxyglycosylation product of the monohydroxy compound 1Gα

[0110] The standard procedure (2) was used: 1 (30.0 mg, 72 μmol) was glycosylated with G (22.4 mg, 60 μmol) to give 1Gα (41.6 mg, 88%) as a white solid. 1H NMR (400MHz, CDCl3) δ7.52–7.15(m,25H,ArH),5.51(s,1H,PhCHO2),5.14(d,J=3.3Hz,1H,1'-H),4.93–4.88(m,2H,1-H,OCH2Ph),4.85(d,J=11.4Hz,1H ,OCH2Ph),4.65(d,J=11.4Hz,1H,OCH2Ph),4.58(d,J=11.6Hz,1H,OCH2Ph),4.52(s,2H,OCH2Ph),4.37(s,2H,OCH2Ph),4.27(dd,J=10.0,4.7Hz,1H,6a- H),4.19(t,J=6.5Hz,1H,5'-H),3.95–3.85(m,3H,H-2,3-H,3'-H),3.80(td ,J=9.9,4.6Hz,1H,5-H),3.75(s,1H,4'-H),3.70(d,J=10.2Hz,1H,6b-H),3 .62–3.50(m,2H,6a'-H,4-H),3.47–3.44(m,1H,6b'-H),3.43(s,3H,OCH3), 2.25(td,J=12.4,3.6Hz,1H,2a'-H),2.07(dd,J=12.7,4.7Hz,1H,2b'-H). Such as Figure 7 shown.

[0111] 2.3 The receptor is the 2-deoxyglycosylation product 1Hα of the monohydroxy compound

[0112] The standard procedure (2) was used: 1 (30.0 mg, 72 μmol) was glycosylated with H (26.9 mg, 60 μmol) to give 1Hα (43.6 mg, 84%) as a white solid. 11H NMR (400 MHz, CDCl3) δ 7.66 (d, J = 7.5 Hz, 2H, ArH), 7.49 (d, J = 7.5 Hz, 2H, ArH), 7.36–7.09 (m, 21H, ArH), 6.74 (d, J = 8.3 Hz, 2H, ArH), 5.83 (d, J = 8.8 Hz, 1H, Fmoc-NH), 5.12 (d, J = 11.9 Hz, 1H, OCH2Ph), 4.98 (d, J = 11.9 Hz, 1H, OCH2Ph), 4.81 (d, J = 11.6 Hz, 1H, OCH2Ph), 4.72 (d, J = 3.4 Hz, 1H, 1-H), 4.54–4.42 (m, 4H, Ser-αH, OCH2Ph, PMB-CH2), 4.38 (d, J = 11.8 Hz, 1H, OCH2Ph), 4.28 (dq, J = 10.1, 5.1, 3.8 Hz, 3H, OCH2Ph, Fmoc-CH2), 4.11 (t, J = 7.2 Hz, 1H, Fmoc-CH), 3.88 (dd, J = 10.8, 3.6 Hz, 1H, Ser-βH(×1)), 3.77–3.61 (m, 7H, OCH3, 3-H, 4-H, 5-H, Ser-βH(×1)), 3.53–3.35 (m, 2H, 6a-H, 6b-H), 2.04 (td, J = 12.4, 3.8 Hz, 1H, 2a-H), 1.73 (dd, J = 12.6, 4.5 Hz, 1H, 2b-H). As Figure 8 shown. 13CNMR(100MHz,CDCl3)δ169.11(C=O),158.78(CO),154.98(CO),142.86(Fmoc-C),142.81(Fmoc-C),140.24(Fmoc-C),140.23(Fmoc-C),137.73(4℃),13 7.34(4℃),136.97(4℃),129.25(CH),127.38(CH),127.30(CH),127.17(CH) ,126.71(CH),126.64(CH),126.58(CH),126.56(CH),126.50(CH),126.45(C H),126.34(CH),126.03(CH),124.09(CH),118.91(CH),112.93(CH),98.18 (C-1),73.32(C-3),73.22(CH2Ph),72.36(CH2Ph),71.77(C-4),69.37(C-5 ,PMB-CH2),68.43(C-6),67.88(Ser-βCH2),66.11(Fmoc-CH2),66.05(CH2Ph),54.18(OCH3),53.64(Ser-αCH),46.10(Fmoc-CH),29.84(C-2).ESI-HRMS Calcd for C 53 H 53 KNO 10

[0113] [M+K] + :902.3302,found:902.3312.

[0114] 2.4 The receptor is the 2-deoxyglycosylation product 1Iα of the monohydroxy compound

[0115] The standard procedure (2) was used: 1 (30.0 mg, 72 μmol) was glycosylated with I (27.7 mg, 60 μmol) to give 1Iα (46.5 mg, 88%) as a white solid. 11H NMR (400 MHz, CDCl3) δ 7.77 (d, J = 7.6 Hz, 2H, ArH), 7.62 (d, J = 7.5 Hz, 2H, ArH), 7.44–7.21 (m, 23H, ArH), 6.88–6.81 (m, 2H, ArH), 5.40 (d, J = 9.9 Hz, 1H, FmocNH), 5.16 (d, J = 11.8 Hz, 1H, OCH2Ph), 5.04 (d, J = 11.7 Hz, 1H, OCH2Ph), 4.90 (d, J = 11.6 Hz, 1H, OCH2Ph), 4.72 (d, J = 3.6 Hz, 1H, 1-H), 4.58 (d, J = 12.1 Hz, 3H, OCH2Ph), 4.51–4.32 (m, 5H, OCH2Ph, Thr-αH, Fmoc-CH2), 4.30–4.22 (m, 2H, Thr-βH, Fmoc-CH), 3.87 (d, J = 5.4 Hz, 2H, 4-H, 5-H), 3.81–3.67 (m, 4H, 3-H, OCH3), 3.53 (qd, J = 9.2, 6.2 Hz, 2H, 6a-H, 6b-H), 1.96 (td, J = 12.5, 4.0 Hz, 1H, 2a-H), 1.62 (dd, J = 12.8, 4.8 Hz, 1H, 2b-H), 1.22 (d, J = 6.4 Hz, 3H, Thr-γH(×3)). As Fig. 9 shown. 13C NMR (100MHz, CDCl3) δ170.58(C=O),159.98(CO),156.68(CO),143.98(Fmoc-C ),143.74(Fmoc-C),141.33(Fmoc-C),138.85(4℃),138.37(4℃),138.05(4℃),1 30.59(CH),128.42(CH),128.37(CH),128.21(CH),128.18(CH),127.74(CH), 127.67(CH),127.63(CH),127.52(CH),127.45(CH),127.24(CH),127.12(CH), 127.09(CH),125.13(CH),125.10(CH),120.00(CH),114.13(CH),99.77(C-1) ,75.62(Thr-βC),74.28(CH2Ph),74.21(C-3),73.51(CH2Ph),73.02(C-4),70. 34(C-5),70.30(PMB-CH2),69.49(C-6),67.24(Fmoc-CH2,CH2Ph),59.06(Thr -αC),55.27(OCH3),47.25(Fmoc-CH),31.06(C-2),18.54(Thr-γCH).ESI-HRMS Calcd for C 54 H 59 N2O 10 [M+NH4] + :895.4165,found:895.4178.

[0116] 2.5 The receptor is a 2-deoxyglycosylation product of a monohydroxy compound 4Gα

[0117] The standard procedure (2) was used: 4 (30.0 mg, 48 μmol) was glycosylated with G (14.8 mg, 40 μmol) to give 4Gα (36.0 mg, 90%) as a colorless oil. 11H NMR (400 MHz, CDCl3) δ 7.70 (ddq, J = 6.6, 2.8, 1.6 Hz, 4H, ArH), 7.51–7.14 (m, 17H, ArH), 5.45 (s, 1H, PhCHO2), 5.07 (d, J = 3.5 Hz, 1H, 1’-H), 5.00 (d, J = 3.3 Hz, 1H, 1-H), 4.88 (d, J = 11.7 Hz, 1H, OCH2Ph), 4.77 (d, J = 11.7 Hz, 1H, OCH2Ph), 4.28 (dd, J = 10.1, 4.7 Hz, 1H, 6a-H), 4.12 (ddd, J = 11.2, 8.2, 5.2 Hz, 1H, 3’-H), 4.01–3.85 (m, 4H, CH2, 2-H, 3-H, 5’-H, 6a’-H), 3.79 (ddd, J = 11.0, 5.9, 3.2 Hz, 2H, 5-H, 6b’-H), 3.68 (t, J = 10.2 Hz, 1H, 6b-H), 3.52 (td, J = 9.5, 8.9, 1.7 Hz, 2H, 4-H, 4’-H), 3.45 (s, 3H, OCH3), 2.24 (dd, J = 13.5, 5.4 Hz, 1H, 2a’-H), 1.75 (ddd, J = 13.5, 11.2, 3.8 Hz, 1H, 2b’-H), 1.14–0.82 (m, 34H, 4×Si(CH(CH3)2), SiPh2C(CH3)3). As Fig.18 shown 13 13C NMR (100 MHz, CDCl3) δ

[0118] 138.84(4 °C), 137.42(4 °C), 135.83(4 °C), 135.69(4 °C), 133.90(CH), 133.70(CH), 129.47(CH), 129.44(CH), 128.85(CH), 128.15(CH), 128.14(CH), 127.59(CH), 127.54(CH), 127.51(CH), 127.49(CH), 127.26(CH), 126.08(CH), 101.26(PhCHO2), 97.11(C-1), 92.76(C-1’), 81.34(C-4), 77.98(C-3), 75.08(CH2Ph), 74.41(C-4’), 73.28(C-2), 73.15(C-5’), 71.86(C-3’), 69.05(C-6), 63.58(C-6’), 62.56(C-5), 55.14(CH2Ph), 37.83(C-2’), 27.03(SiC(CH3)(CH3)(CH3)), 19.42(SiC(CH3)3), 17.55(Si(CH(CH3)(CH3)), 17.41(Si(CH(CH3)(CH3)), 17.39

[0119] (Si(CH(CH3)(CH3)), 17.33(Si(CH(CH3)(CH3)), 17.29(Si(CH(CH3)(CH3)), 12.94(Si(CH(CH3)2)2), 12.84(Si(CH(CH3)2)2), 12.27(2×Si(CH(CH3)2)2). ESI-HRMS Calcd for C 55 H 82 O 11 NSi3[M+

[0120] NH4] + : 1016.5191, found: 1016.5197.

[0121] Example 3: Synthesis of 2-Deoxyglucan 9

[0122]

[0123] Compound 2A (930.0 mg, 0.9 mmol) was dissolved in a TBAF solution containing 1 M tetrahydrofuran, stirred at room temperature for 2 h, detected by TLC plate until the reaction was complete, diluted with ethyl acetate, the organic layer was washed with H2O and NaCl (aq.), and dried with Na2SO4, filtered and the solvent was removed under reduced pressure distillation. The resulting residue was purified by silica gel column chromatography to obtain compound 6 (652.0 mg, 91%) as a white foam. 1 H NMR (400MHz, CDCl3) δ7.41–7.18(m,25H,ArH),5.04(d,J=3.3Hz,1H,1'-H),4.99(d,J=10.8Hz,1H,OCH2Ph),4.93(d,J=11.7Hz,1H,OCH2Ph),4.87(d,J=11. 3Hz,1H,OCH2Ph),4.79(d,J=11.5Hz,2H,OCH2Ph),4.71–4.54(m,5H,OCH2Ph, 1-H), 4.46 (d, J=11.3Hz, 1H, OCH2Ph), 3.98 (t, J=9.2Hz, 1H, 3-H), 3.83 (dt, J=

[0124] 11.7,3.7Hz,1H,3'-H),3.80–3.69(m,3H,6a-H,4'-H,5'-H),3.63(ddd, J=10.4,6.1,3.6Hz,1H,6a-H),3.58–3.49(m,3H,6b-H,2-H,5-H),3.43(m ,2H,6b'-H,4-H),3.32(s,3H,OCH3),2.19(td,J=12.3,3.6Hz,1H,2a'-H),2.03(dd,J=12.6,4.5Hz,1H,2b'-H),1.61(dd,J=8.9,3.7Hz,1H,OH). Such as Fig.21 shown.

[0125] The standard procedure (1) was used: 2 (30.0 mg, 53 μmol) was glycosylated with 6 (35.0 mg, 44 μmol) to give 7 (50.0 mg, 83%) as a colorless oil. 11H NMR (400 MHz, CDCl3) δ 7.65–7.60 (m, 4H, Ar), 7.41–7.14 (m, 41H, Ar), 5.02 (d, J = 3.3 Hz, 1H, 1’-H), 4.98 (d, J = 10.7 Hz, 1H, OCH2Ph), 4.91 (dd, J = 11.7, 3.6 Hz, 2H, OCH2Ph), 4.80 (dd, J = 19.4, 11.1 Hz, 3H, OCH2Ph), 4.71–4.46 (m, 10H, 1-H, 1”-H, OCH2Ph), 3.98 (t, J = 9.2 Hz, 1H, 3-H), 3.91–3.83 (m, 2H, 3’-H, 4”-H), 3.80 (dd, J = 11.5, 4.3 Hz, 1H, 6a-H), 3.73 (m, 6H, 3”-H, 4’-H, 5’-H, 5”-H, 6a”-H, 6b”-H), 3.68 (dd, J = 4.7, 2.0 Hz, 1H, 5-H), 3.66–3.62 (m, 1H, 6a’-H), 3.59–3.45 (m, 3H, 2-H, 4-H, 6b-H), 3.31 (s, 4H, OCH3, 6b’-H), 2.21 (td, J = 12.3, 3.6 Hz, 1H, 2a’-H), 2.14–1.98 (m, 2H, 2b’-H, 2a”-H), 1.73 (dd, J = 12.5, 4.6 Hz, 1H, 2b”-H), 1.04 (s, 9H, SiPh2C(CH3)3). As Fig. 22 shown. 13 13C NMR (100 MHz, CDCl3) δ 138.97 (4 °C), 138.76 (4 °C), 138.73 (4 °C), 138.62 (4 °C), 138.41 (4 °C), 138.39 (4 °C), 138.15 (4 °C), 135.59 (CH), 135.56 (CH), 133.52 (4 °C), 133.33 (4 °C), 129.71 (CH),

[0126] 128.52(CH),128.49(CH),128.44(CH),128.29(CH),128.27(CH),128.16(CH),128. 10(CH),128.07(CH),128.02(CH),127.96(CH),127.76(CH),127.69(CH),127.63(C H),127.60(CH),127.57(CH),127.46(CH),127.38(CH),127.27(CH),98.45(C-1'), 97.95(C-1),97.33(C-1”),82.14(C-3),80.09(C-2),77.91(C-4),75.86(CH2Ph),75 .01(CH2Ph),74.97(C-3”),74.51(C-3’),74.32(CH2Ph),74.02(CH2Ph),73.36(CH2 Ph),72.85(C-4”),72.73(C-4’),71.43(C-5”),70.40(CH2Ph),70.30(CH2Ph),70.0 4(C-5),69.61(C-5'),66.12(C-6'),65.91(C-6),63.14(C-6”),55.10(OCH3),31.1 6(C-2”),30.87(C-2’),26.96(SiC(CH3)(CH3)(CH3)),19.25(SiC(CH3)3).ESI-HRMS Calcd for C 84 H 94 KO 14 Si[M+K] + :1393.6044,found:1393.6059.

[0127] Compound 7 (770.0 mg, 0.57 mmol) was dissolved in a TBAF solution containing 1 M tetrahydrofuran, stirred at room temperature for 2 h, detected by TLC plate until the reaction was complete, diluted with ethyl acetate, the organic layer was washed with H2O and NaCl (aq.), and dried with Na2SO4, filtered and the solvent was removed under reduced pressure distillation. The resulting residue was purified by silica gel column chromatography to obtain compound 8 (539.0 mg, 85%) as a white foam. 1H NMR (400MHz, CDCl3) δ7.40–7.17(m,35H,ArH),5.00(d,J=3.3Hz,1H,1'-H),4.97(d,J=1 0.7Hz,1H,OCH2Ph),4.92(dd,J=11.8,2.4Hz,2H,OCH2Ph),4.83(d,J=11.0Hz,1H,OCH2Ph) ),4.80–4.74(m,2H,OCH2Ph),4.69–4.66(m,2H,OCH2Ph,1-H),4.66–4.57(m,5H,OCH2Ph, 1”-H),4.52(d,J=12.3Hz,3H,OCH2Ph),3.97(t,J=9.2Hz,1H,3-H),3.86(dd,J=11.3,4.1 Hz,1H,3'-H),3.79–3.62(m,7H,3”-H,4-H,4’-H,4”-H,5’-H,6a-H,6a’-H),3.60–3.54( m,2H,6b-H,6a”-H),3.53–3.49(m,2H,2-H,5-H),3.48–3.34(m,3H,5”-H,6b’-H,6b”-H), 3.31(s,3H,OCH3),2.18(td,J=12.1,3.4Hz,1H,2a'-H),2.05(qd,J=14.0,13.3,4.0Hz,2 H,2a”-H,2b’-H),1.85(dd,J=8.8,3.7Hz,1H,OH),1.76(dd,J=12.6,4.3Hz,1H,2b”-H). Such as Fig.23 shown.

[0128] The standard procedure (1) was used: 2 (212.0 mg, 0.38 mmol) was glycosylated with 8 (350.0 mg, 0.31 mmol) to give 9 (423.0 mg, 80%) as a white foam. 11H NMR (400 MHz, CDCl3) δ 7.68–7.54 (m, 4H, ArH), 7.37–7.17 (m, 53H, ArH), 5.00 (d, J = 3.3 Hz, 1H, 1’-H), 4.97–4.86 (m, 4H, OCH2Ph), 4.81–4.72 (m, 3H, OCH2Ph), 4.71 (d, J = 3.3 Hz, 1H, 1”’-H), 4.69–4.55 (m, 8H, OCH2Ph, 1-H, 1”-H), 4.55–4.47 (m, 6H, OCH2Ph), 3.96 (m, 2H, 3-H, 4”’-H), 3.90 (m, 2H, 3’-H, 3”’-H), 3.82–3.76 (m, 4H, 4’-H, 5”’-H, 6a-H, 6a”’-H), 3.75–3.61 (m, 8H, 3”-H, 4”-H, 5-H, 5’-H, 5”-H, 6a’-H, 6a”-H, 6b”’-H), 3.53–3.43 (m, 3H, 2-H, 4-H, 6b-H), 3.37 (dd, J = 9.4, 7.0 Hz, 1H, 6b’-H), 3.30 (dd, J = 9.8, 5.9 Hz, 1H, 6b”’-H), 3.25 (s, 3H, OCH3), 2.11 (dddd, J = 36.7, 24.3, 12.2, 4.1 Hz, 4H, 2a’-H, 2b’-H, 2a”-H, 2a”’-H), 1.84 (dd, J = 12.6, 4.4 Hz, 1H, 2b”’-H),

[0129] 1.72 (dd, J = 12.5, 4.3 Hz, 1H, 2b”-H), 1.03 (s, 9H, SiPh2C(CH3)3). As Fig.24 shown. 13 13C NMR (100 MHz, CDCl3) δ 139.04 (4 °C), 138.77 (4 °C), 138.69 (4 °C), 138.68 (4 °C), 138.52 (4 °C), 138.39 (4 °C), 138.18 (4 °C), 135.54 (4 °C), 135.53 (4 °C), 133.54 (CH), 133.30 (CH), 129.75 (4 °C),

[0130] 129.68(4℃),128.48(CH),128.48(CH),128.43(CH),128.40(CH),128.37(CH),128.34(CH),128.31(CH),128.2 6(CH),128.13(CH),128.06(CH),128.03(CH),127.93(CH),127.78(CH),127.73(CH),127.67(CH),127.65(CH) ,127.62(CH),127.58(CH),127.56(CH),127.53(CH),127.47(CH),127.44(CH),127.29(CH),127.23(CH),98.5 8(C-1'),97.96(C-1),97.70(C-1”),97.45(C-1”’),82.10(C-3),80.11(C-2),77.83(C-4)75.82(CH2Ph),75.14 (C-3”'),75.03(C-3”),74.89(CH2Ph),74.59(C-3’),74.36(CH2Ph),74.01(CH2Ph),73.98(CH2Ph),73.30(CH2 Ph),72.93(C-4”'),72.82(C-4”),72.49(C-4’),71.45(C-5”’),70.48(CH2Ph),70.41(CH2Ph),70.33(CH2Ph),6 9.99(C-5),69.84(C-5'),69.23(C-5”),66.25(C-6”),66.09(C-6’),66.01(C-6),62.90(C-6”’),55.08(OCH3) ,31.29(C-2”'),31.04(C-2”),30.85(C-2’),26.93(SiC(CH3)(CH3)(CH3)),19.21(SiC(CH3)3).ESI-HRMSCalcd for C 104 H 124 O 18 NSi[M+NH4] + :1699.8303,found:1699.8230.

[0131] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. For those skilled in the art, the present invention may have various modifications and variations. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included in the protection scope of the present invention.

Claims

1. A 2-deoxyglycosidation reaction catalyst, characterized in that: The catalyst is mercuric trifluoromethanesulfonate.

2. An application of mercuric trifluoromethanesulfonate as a catalyst in 2-deoxyglycosidation reaction.

3. A method for catalyzing the glycosidation of a sugar ene donor, characterized in that: Mercuric trifluoromethanesulfonate is used as a catalyst to catalyze the glycosylation reaction between the sugar ene donor and the acceptor to obtain a 2-deoxyglycosylated product.

4. The method for catalyzing the glycosidation of a sugar ene donor as claimed in claim 3, characterized in that: The glycoene donor is any one of compounds 1-5, and the chemical structures of compounds 1-5 are shown below: Or, the receptor is any one of compounds AJ, and the chemical structures of compounds AJ are shown below; 5. The method for catalyzing the glycosidation of a sugar ene donor as claimed in claim 3, characterized in that: The molar ratio of the acceptor, the glycoene donor and mercuric trifluoromethanesulfonate is 1:1.10-1.30:0.09-0.

11.

6. The method for catalyzing the glycosidation of a sugar ene donor as claimed in claim 3, characterized in that In an inert atmosphere, the acceptor, the glycoene donor and the molecular sieve are added to an anhydrous solvent, stirred evenly at a temperature of -2 to 2°C, and then mercuric trifluoromethanesulfonate is added to carry out a glycosidation reaction.

7. The method for catalyzing the glycosidation of a sugar ene donor as claimed in claim 6, characterized in that: The solvent is Toluene, and compound A, compound B, compound D, compound E, compound F or compound J is used as the receptor; Or the solvent is Toluene / DCM, Compound 1 and Compound 4 are used as glycoene donors, and Compound C, Compound G, Compound H, and Compound I are used as acceptors.

8. The method for catalyzing the glycosidation of a sugar ene donor as claimed in claim 6, characterized in that: After the glycosylation reaction, Et3N was added to quench the reaction, diluted with DCM, and the precipitate was filtered out through a celite pad; the organic layer was washed with NaHCO3 solution and NaCl solution, and dried with Na2SO4, filtered and the solvent was removed under reduced pressure distillation; the resulting residue was purified by silica gel column chromatography to obtain the corresponding 2-deoxyglycosylation product.

9. Use of the above-mentioned 2-deoxyglycosidation reaction catalyst or the method for catalyzing the glycosidation of a sugar ene donor in constructing the O-glycosidic bond of a 2-deoxy sugar substance.

10. The use according to claim 9, characterized in that: Preparation of 2-deoxy polysaccharides by constructing O-glycosidic bonds of 2-deoxy sugar substances; Alternatively, compound 2 is glycosylated with compound A under the catalysis of mercuric trifluoromethanesulfonate to prepare compound 2A; Compound 6 was obtained by removing the TBDPS protecting group from compound 2A; Then, under the catalysis of mercuric trifluoromethanesulfonate, compound 2 and compound 6 are glycosylated to prepare compound 7; Compound 7 was deprotected by TBDPS to obtain compound 8; Then, under the catalysis of mercuric trifluoromethanesulfonate, compound 2 is glycosylated with compound 8 to prepare compound 9.

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