TFA-induced conversion of glycals to 2-deoxy-sugars and their utility in synthesizing 2-deoxy-glycosyl esters

Abstract

The conversion of glycals into 2-deoxy sugars is revealed under environmentally friendly reaction conditions at room temperature. This efficient method is so robust that numerous protected or unprotected glycals were successfully converted into their respective 2-deoxy sugars with yields up to 98%. Moreover, the produced 2-deoxy sugars underwent coupling reactions to generate a diverse collection of 2-deoxy-glycosyl esters with carboxylic acids. This library of glycosyl esters was synthesized by employing a range of acids, including readily available drugs like indomethacin, tolmetin, and others. A plausible route for generating 2-deoxy sugars was also demonstrated where the double bond of glycals is activated with an activator and simultaneous attack of a hydroxyl group on the anomeric carbon leading to the formation of desired products.