Abstract
The nitrate ester, formed by reaction with fuming nitric acid in acetic anhydride at 0 °C, was suitable to block free hydroxyl groups in partially acetylated sugars without acetyl migration. This allowed the acetylated positions in partially acetylated mono- and disaccharides to be located by the reaction sequence: nitration, deacetylation, methylation, de-nitration, disaccharide hydrolysis and methyl glycosylation (initial product identification by paper partition chromatography), acetylation, and analysis of the products by gas-liquid partition chromatography. D-Glucose, penta-O-acetyl-D-glucopyranose, and 2,3-di-O-acetyl-β-D-glucopyranose were used as test compounds in the evaluation of this scheme.
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