The use of anhydroiminocyclitols as glycosyl donors in glycosidation reactions

High yielding synthesis of six- and five-membered N-substituted iminosugar glycosides and of five-membered iminosugar thioglycosides by nucleophilic opening of both new and previously described N-diethoxycarbonylvinyl anhydroiminosugar derivatives (glycosyl donors) with primary alcohols, primary thiols, and thiophenol (glycosyl acceptors) is reported. The reactions are highly stereoselective, with anomeric ratios better than 4:1.