Preparative scale synthesis ofO-glycosides and of a disaccharide by electrochemical oxidation of phenylS-glycosides

Summary O-glycosides were synthesized by electrochemical oxidation of phenylS-glycosides in the presence of primary alcohols in acetonitrile. Similarly, a -linked disaccharide was obtained selectively by oxidation of phenylS-glycoside in the presence of a sugar alcohol. Electrosyntheses were performed under controlled potential or at constant current, in an undivided cell, on a large scale. 1 to 60 g of phenylS-glycosides in 0.5 to 1 dm³ of acetonitrile were converted with chemical yields in the range of 65–75%.