Facile triflic acid-catalyzed α-1,2-cis-thio glycosylations: scope and application to the synthesis of S-linked oligosaccharides, glycolipids, sublancin glycopeptides, and TN/TF antigens

摘要

Studies of S -linked glycoconjugates have attracted growing interest because of their enhanced chemical stability and enzymatic resistance over O -glycoside counterparts. We here report a facile approach to access α-1,2- cis-S -linked glycosides using triflic acid as a catalyst to promote the glycosylation of a series of thiols with D -glucosamine, galactosamine, glucose, and galactose electrophiles. This method is broadly applicable for the stereoselective synthesis of S -linked glycopeptides, oligosaccharides and glycolipids in high yield and excellent α-selectivity. Many of the synthetic limitations associated with the preparation of these S -linked products are overcome by this catalytic method.