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

•Thioglycosides can be readily prepared from per-acetylated carbohydrate donors.•S-Glycosylations are catalyzed using the minimally competent Lewis acid InBr3.•Only β anomers are formed.•Glycosylation of cysteine and a library of thio-glycolipids are produced by Zemplèn deacylation. 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 CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplén 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 (1H and 13C, including COSY, HSQC and HMBC) are reported for compounds not previously described.