Fe(III)-catalyzed stereoselective synthesis of deoxyglycosides using stable bifunctional deoxy-phenylpropiolate glycoside donors

Abstract

Herein, we report a mild and economical route for the stereoselective synthesis of 2-deoxy and 2,6-dideoxyglycosides via FeCl₃-catalyzed activation of bench stable deoxy-phenylpropiolate glycosyl donors (D-PPGs). Optimized reaction conditions work well under additive-free conditions to afford the corresponding 2-deoxy and 2,6-dideoxyglycosides in good yields with high α-anomeric selectivity by reacting with sugar and non-sugar-based acceptors. The optimized conditions were also extended for disarmed D-PPG donors. In addition, the developed strategy is amenable to high-scale-up synthesis.

Keywords: Additive-free glycosylation; Bifunctional donors; Deoxyglycosides; Stereoselective.