Abstract
Oxidation of the primary alcohol group (-CH2OH) in sugar acetates to carboxylic acid group (-COOH) had been effected by potassium permanganate method reported by Stacey but this was found to be not applicable to disaccharides like heptaacetyimaltose (I) and hexaacetylmaltose (II) because the reaction rate is extremely small and the yield is low. Oxidation agents to be used in such cases were examined and the concurrent use of chromium trioxide and potassium permanganate was found to be a good method. Application of 2/3 mole of chromium trioxide to 1 mole of primary alcohol in I and II under limited conditions and subsequent oxidation with potassium permanganate afforded heptaacetyl-4-O-(α-D-glucopyranosiduronyl)-D-glucose (III) and hexaacetyl-4-O-(α-D-glucopyranosiduronyl)-D-glucuronic acid (IV), which were deacetylated respectively to 4-O-(α-D-glucopyranosiduronyl)-D-glucose (VII) and 4-O-(α-D-glucopyranosiduronyl)-D-glucuronic acid (VIII). The reaction rate of this oxidation is very large and the yield is very high but the condition of chromium trioxide oxidation is very limited and the sugar is decomposed outside this condition, Various properties of the new compound (VIII), especially the result of its acid hydrolysis, are discussed.
