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TEMPO‐Mediated Anodic Oxidation of Methyl Glycosides and 1‐Methyl and 1‐Azido Disaccharides
Author(s) -
Schämann Matthias,
Schäfer Hans J.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390041
Subject(s) - chemistry , cellobiose , maltose , glycoside , lactose , organic chemistry , electrolyte , disaccharide , anode , cellulose , electrode , sucrose , cellulase
Methyl glycosides of L ‐sorbopyranoside, D ‐fructopyranoside, D ‐glucosaminopyranoside, 2,3‐dehydro‐2,3‐dideoxyglucopyranoside, 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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)