Saccharoascorbic acid

Oxidation of the monoacetone derivative, 2,3-isopropylidene-L-sorbose (XLIX), with air in the presence of platinum has reportedly given L-gulo-saccharoascorbic acid (LI), after treatment of the unstable intermediate 2,3-isopropylidene-2,5-furanose-L-gulosaccharic acid (L) with hydrochloric acid. 109... 

Saccharoascorbic acid, 35, has been proposed as a minor metabolite of ascorbic acid in animals (57-60). The isolation of ascorbic acid 2-0-sulfate, 18, in a variety of animal species and the remarkable oxidative stability of the 2-0-sulfate substituted enonolactone moiety have prompted suggestions (60) that saccharoascorbic acid 2-0-sulfate, 34, is a catabolite of 18 in vivo. 

Stuber and Tolbert (61) utilized the oxidative stability of the 2-0-sulfate in a short synthesis of both saccharoascorbic acid and saccharoascorbic acid 2-0-sulfate. Oxidation of ascorbic acid 2-0-sulfate, 18, with platinum and oxygen afforded good yields of acid 34 under conditions in which ascorbic acid itself is oxidized to dehydroascorbic acid. Hydrolysis of the sulfate in acid afforded saccharoascorbic acid, 35, in good yield. 

New derivatives of L-ascorbic acid have been synthesized including saccharoascorbic acid, 5-ketoascorbic acid, 2-phosphoric-ascorbic acid, 6-bromo-6-deoxyascorbic acid, 6-chloro-6-deoxyascorbic acid, the 5,6-dehydro-5,6-dideoxy derivative, the 4,5-dehydro-5-deoxy derivative, the 5,6-dideoxy derivative, and numerous nitrogen derivatives. 

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