Electroorganic synthesis 66: Selective anodic oxidation of carbohydrates mediated by TEMPO

Authors
Schnatbaum, K Schafer, HJ
Citation
K. Schnatbaum et Hj. Schafer, Electroorganic synthesis 66: Selective anodic oxidation of carbohydrates mediated by TEMPO, SYNTHESIS-S, (5), 1999, pp. 864-872
Citations number
51
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881 → ACNP
Issue
5
Year of publication
1999
Pages
864 - 872
Database
ISI
SICI code
0039-7881(199905):5<864:ES6SAO>2.0.ZU;2-4
Abstract
The carbohydrates 4-15 are anodically oxidized with 2,2,6,6-tetramethylpipe ridin-1-oxyl (TEMPO) as mediator. Selective and complete reaction at the pr imary hydroxyl groups affords the corresponding carboxylic acids 16-32 in m oderate to excellent yield. Methyl alpha-D-glucopyranoside is converted in 98% yield to the uronic acid 16. Cyclic voltammetry shows that the oxydatio n is base-catalyzed and the oxidation of the hydroxy group with TEMPO+ (2) is rate determining.