Zinc Acetate Catalyzed Stereoselective 1,2-trans-Glycosylation Using Glycosyl Chlorides

Abstract

We report a strategy for the stereoselective synthesis of 1,2-trans-glycosides in the absence of neighboring group participation. The present protocol for the selective glycosylation mainly relies on catalyst control rather than protecting group selection. By using this protocol, several glycosides were prepared. Zinc acetate was found to be the optimal catalyst, providing the desired 1,2-trans-glycosides from glucose- and mannose-derived glycosyl halides at room temperature instead of low-temperature conditions.

Keywords

• glycosyl chloride
• no neighboring group participation
• 1,2-trans-glycosylation
• zinc acetate