Stereospecific synthesis of 1,2-cis-glycosides of 2-aminosugars

A high-stereospecific method of 1,2-cis-glycosylation based on the use of 1,2-trans-glycosyl thiocyanates as glycosyl group donors is developed. The new method of 1,2-cis-glucosaminide bond formation and its stereospecificity were tested with a number of derivatives of 2-azido-2-desoxy-α-D-glucosylglucose with glucosaminide bond of different type. The structure of disaccharides obtained was confirmed using 1H and 13C NMR spectroscopy technique. Thus, for the first time a method is developed that makes it possible to prepare stereoregular 1,2-cis-di- and oligosaccharides containing aminosugars.