4-AcNH-TEMPO-CATALYZED OXIDATION OF ALDOSES TO ALDARIC ACIDS USING CHLORINE OR BROMINE AS TERMINAL OXIDANTS

The 4-AcNH-TEMPO-catalyzed oxidation of d-glucose to d-glucaric acid using elemental chlorine or bromine as the terminal oxidant is reported. The pH and temperature of the reactions were closely controlled to be between 0-5°C and pH 11.5, respectively. Spectroscopically ( 1 H NMR) determined yields...

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Bibliographic Details
Published in:Journal of carbohydrate chemistry 2002-05, Vol.21 (1-2), p.65-77
Main Authors: Merbouh, Nabyl, Bobbitt, James M., Brückner, Christian
Format: Article
Language:English
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Summary:The 4-AcNH-TEMPO-catalyzed oxidation of d-glucose to d-glucaric acid using elemental chlorine or bromine as the terminal oxidant is reported. The pH and temperature of the reactions were closely controlled to be between 0-5°C and pH 11.5, respectively. Spectroscopically ( 1 H NMR) determined yields of glucarate were greater than 90%; yields of crystalline monopotassium d-glucarate (or disodium d-glucarate), isolated and purified by precipitation, were between 70 and 85%. Oxidations of mannose to mannaric acid and galactose to mucic acid were also demonstrated.
ISSN:0732-8303
1532-2327
DOI:10.1081/CAR-120003738