Glycosylation Using Methylthioglycosides of N-Acetylneuraminic Acid and Dimethyl(Methylthio)Sulfonium Triflate

Abstract Recently, great interest has been focussed on the synthesis of oligosaccharides containing N-acetylneuraminic acid (Neu5Ac) because of its important roles in a variety of biological recognitions.2 However, many difficulties in the synthesis of naturally occurring α-glycosides still remained.3 We have recently reported the stereo-selective synthesis of a series of α- and β-2-thio-neuraminyl glycosides.1-4 In the meantime, the utility of thioglycosides in oligosaccharide synthesis has been widely developed.5 Particularly noteworthy is the dimethyl(methylthio)sulfonium triflate (DMTST) promoted glyco-sylation method5k.1 because excellent yields are achieved due to the high thiophilicity of this reagent.

[1]  M. Kiso,et al.  Stereoselective Synthesis of 5′-S-(5-Acetamido-3,5-dideoxy-D-glycero-α-and-β-D-Galacto-2-nonulopyranosylonic Acid)-5′-thio Cytidixe , 1987 .

[2]  M. Kiso,et al.  Synthesis of 3-S-C (5-Acetamido-3.5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic Acid)-3-thio-galactopyranose Derivatives , 1987 .

[3]  P. Garegg,et al.  A novel promoter for the efficient construction of 1,2-trans linkages in glycoside synthesis, using thioglycosides as glycosyl donors , 1986 .

[4]  M. Kiso,et al.  Synthesis of 6-S-(5-Acetamido-3,5-Dideoxy-D-Glycero-α-D-Galacto-2-Nonulopyranosylonic Acid)-6-Thio-Hexopyranosides , 1986 .

[5]  M. Kiso,et al.  Studies on the Thioglycosides of N-Acetylneuraminic Acid 1: Synthesis of Alkyl α-Glycosides of 2-Thio-N-Acetylneuraminic Acid , 1986 .

[6]  H. Paulsen,et al.  Glycosidsynthese von N-acetylneuraminsäure mit sekundären Hydroxylgruppen , 1986 .

[7]  M. Nashed,et al.  Synthesis of 1,2-cis-linked glycosides using dimethyl(methylthio)sulfonium triflate as promoter and thioglycosides as glycosyl donors , 1986 .

[8]  K. Okamoto,et al.  Syntheses of (α2–9) and (α2–8) linked neuraminylneuraminic acid derivatives , 1986 .

[9]  K. Okamoto,et al.  An effective synthesis of α-glycosides of -acetylneuraminic acid by use of 2β-halo-3β-hydroxy-4,7,8,9-tetra--acetyl--acetylneuraminic acid methyl ester ☆ , 1986 .

[10]  K. Leontein,et al.  Synthesis of the methyl and 1-octyl glycosides of the P-antigen tetrasaccharide (globotetraose). , 1985, Carbohydrate research.

[11]  H. Lönn.  Synthesis of a tri- and a hepta-saccharide which contain alpha-L-fucopyranosyl groups and are part of the complex type of carbohydrate moiety of glycoproteins. , 1985, Carbohydrate research.

[12]  M. Sugimoto,et al.  Synthesis of α-Neu5Acp-(2→3)-d-Gal and α-Neu5Acp-(2→3)-β-d-Galp-(1→4)-d-Glc , 1985 .

[13]  K. Nicolaou,et al.  Practical synthesis of oligosaccharides. Partial synthesis of avermectin B1a , 1984 .

[14]  H. Paulsen,et al.  Synthese eines trisaccharides aus N-acetylneuraminsäure und N-acetyllactosamin , 1984 .

[15]  H. Lönn,et al.  Synthesis of a nona- and an undeca-saccharide that form part of the complex type of carbohydrate moiety of glycoproteins. , 1983, Carbohydrate research.

[16]  C. Henrichson,et al.  A reinvestigation of glycosidation reactions using 1-thioglycosides as glycosyl donors and thiophilic cations as promoters , 1983 .

[17]  K. Nicolaou,et al.  A mild and general method for the synthesis of 0-glycosides , 1983 .

[18]  S. Hanessian,et al.  Chemistry of the glycosidic linkage. Exceptionally fast and efficient formation of glycosides by remote activation , 1980 .

[19]  J. W. V. Cleve.  Reinvestigation of the preparation of cholesteryl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside , 1979 .

[20]  R. Ferrier,et al.  A potentially versatile synthesis of glycosides , 1973 .