Ring opening of sugar-derived epoxides by TBAF/KHF2: An attractive alternative for the introduction of fluorine into the carbohydrate scaffold

Abstract

A stable and commercially available reagent mixture, composed of tetrabutylammonium bifluoride/potassium bifluoride (TBAF/KHF2), was found to be effective for the nucleophilic ring opening reactions of sugar-derived epoxides with fluoride. Different sugar-derived epoxide precursors, including 1-thio-glycosides can be ring-opened to afford fluorinated carbohydrate products in high yields and in short reaction times.