Abstract
3-Ketoglucuronic acid, a new 1, 3-dicarbonyl carbohydrate, was synthesized. 5-O-Acetyl-1, 2-O-isopropylidene-D-glucofuranurono-6, 3-lactone (I) was converted into methyl 5-O-acety-1, 2-O-isopropylidene-D-glucofuranuronate (IId), which was oxidized with chromium trioxide to give 3-keto-5-O-acetyl-1, 2-O-isopropylidene-D-glucofuranuronate (III). Ethyl acetate was found to be an excellent solvent for this oxidation. Removal of protective groups from III afforded crystalline 3-ketoglucuronic acid (VII). The intermediate substance (III) underwent stereo-selective reduction by the action of lithium aluminum hydride to produce 1, 2-O-isopropylidene-D-allofuranose.
