Electroorganic synthesis 66: Selective anodic oxidation of carbohydrates mediated by TEMPO
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 acids 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.
Schnatbaum, Karsten,Sch?fer, Hans J.
p. 864 - 872
(2007/10/03)
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