Electroorganic Synthesis 66: Selective Anodic Oxidation of Carbohydrates Mediated by TEMPO

Karsten Schnatbaum; Hans J. Schäfer

doi:10.1055/s-1999-3464

Synthesis 1999; 1999(5): 864-872
DOI: 10.1055/s-1999-3464

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Electroorganic Synthesis 66: Selective Anodic Oxidation of Carbohydrates Mediated by TEMPO

Karsten Schnatbaum^* , Hans J. Schäfer

^*Organisch-Chemisches Institut der Universität Münster, Corrensstraße 40, D-48149 Münster, Germany; Fax +49(2 51)8 33 97 72; E-mail: schafeh@uni-muenster.de

Abstract

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The carbohydrates 4-15 are anodically oxidized with 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) as mediator. Selective and complete reaction at the primary hydroxyl groups affords the corresponding carboxylic acid 16-32 in moderate to excellent yield. Methyl α-d-glucopyranoside is converted in 98% yield to the uronic acid 16. Cyclic voltammetry shows that the oxydation is base-catalyzed and the oxidation of the hydroxy group with TEMPO⁺ (2) is rate determining.

anodic oxidation - carbohydrates - TEMPO - cyclic voltammetry - uronic acids

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