Application of 2-Azido-2-deoxythioglycosides for beta-Glycoside Formation and Oligosaccharide Synthesis

Abstract

Most natural 2-acetamido-2-deoxyglycosides exist in a 1,2-trans-beta-glycosidic configuration. This study investigated the use of 2-azido-2-deoxythioglycosides for 1,2-trans-beta-glycosidic bond formation under low-concentration glycosylation conditions. Further application of the 2-azido-2-deoxythioglycosyl substrates for one-pot oligosaccharide synthesis was demonstrated in the synthesis of protected beta-(1?6)-N-acetylglucosamine trimer, core-6serine conjugate, and F1a serine conjugate.