Glycosyl 2-Pyridinecarboxylate as an Effective Glycosyl Donor : Glycosidation of Mannose, 2-Azidosugar, and 2-Deoxysugar into Disaccharides

Abstract

Glycosylation reactions using a glycosyl 2-pyridinecarboxylate as a glycosyl donor were performed. Glycosyl 2-pyridinecarboxylate was designed based on a variation of the Remote Activation Concept and is activated through bidentate coordination to mild Lewis acids such as copper triflate and tin triflate. This method was effective for the glycosidation of not only glucose, but several other sugars such as the mannose-type, 2-azidosugar-type, and 2-deoxysugar-type. Various disaccharides were obtained in excellent yield by this reaction.