Partial Oxidation of Vicinal Hydroxyl Groups of Methyl 4,6-O-Benzylidene-α-and β-D-Glucopyranosides with Dimethyl Sulfoxide and Phosphorus Pentoxide

Abstract

Oxidation of methyl 4,6-O-benzylidene-α-D-glucopyranoside with dimethyl sulfoxide – phosphorus pentoxide gives the corresponding 3-ketone (3), the 2,3-O-oxidomethylenebenzylidene acetal (5), and the 2,3-O-oxidodimethylene acetal (6). By a similar treatment of methyl 4,6-O-benzylidene-β-D-glucopyranoside only starting material was recovered.