Electrochemical conversion of thioglycosides to glycosyl triflates

Abstract

Glycosyl triflates, which serve as important intermediates in glycosylation reactions, were generated and accumulated by low-temperature electrochemical oxidation of thioglycosides, such as thioglucosides, thiogalactosides, and thiomannosides, in the presence of tetrabutyl-ammonium triflate (Bu 4NOTf) as a supporting electrolyte. The solutions of glycosyl triflates thus obtained were then characterized by low-temperature NMR measurements. The thermal stability of glycosyl triflates and their reactions with glycosyl acceptors were also studied. ©2008 FCCA (Forum: Carbohydrates Coming of Age).