Download PDF
Synthesis 1999; 1999(5): 864-872
DOI: 10.1055/s-1999-3464
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 1999 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >