Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis

Abstract Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2- trans- glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl 3 at reflux in the presence of a catalytic amount of InBr 3 . Deacylation of the intermediate peracetates were achieved under Zemplen conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α] D and NMR data ( 1 H and 13 C, including COSY, HSQC and HMBC) are reported for compounds not previously described.