TEMPO-mediated anodic oxidation of methyl glycosides and 1-methyl and 1-azido disaccharides

Methyl glycosides Of L-sorbopyranoside, D-fructopyranoside, D-glucosaminopyranoside, 2,3-dehydro-2,3-dideoxyglucopy-ranoside, cellobiose, lactose, and maltose and the 1-azido derivatives of glucose, cellobiose, lactose, and maltose have been converted into the corresponding uronic acids in moderate to excellent yields by TEMPO-mediated anodic oxidation. The anode proves to be an advantageous alternative to other cooxidants in TEMPO+ oxidations of carbohydrates and is compatible with N-acylamino and azido groups and with double bonds. The electrolyte, a carbonate buffer, can easily be removed with a cation-exchange resin, a facile scale-up by increasing the electrode area is possible. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).