Application of 2‐Azido‐2‐deoxythioglycosides for β‐Glycoside Formation and Oligosaccharide Synthesis

Abstract

Abstract Most natural 2‐acetamido‐2‐deoxyglycosides exist in a 1,2‐ trans ‐β‐glycosidic configuration. This study investigated the use of 2‐azido‐2‐deoxythioglycosides for 1,2‐ trans ‐β‐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 β‐(1→6)‐ N ‐acetylglucosamine trimer, core‐6–serine conjugate, and F1–α serine conjugate.