Abstract
It has been found that the thiocarbonate, or (alkylthio)carbonyl derivative, serves as a versatile blocking group for the synthesis of partial ester derivatives of carbohydrates. The (alkylthio)carbonyl group is readily substituted in pyridine solution, is stable to mild acid conditions, but is decomposed by mild oxidation. Crystalline methyl 4,6-di-O-benzoyl-α-D-glucopyranoside has been synthesized and its structure proved by an independent synthesis of its 2,3-di-O-phenylcarbamate derivative. Methyl 4,6-di-O-benzoyl-β-D-glucopyranoside was also synthesized and its structure proved by acetylation to the known 2,3-di-O-acetyl derivative.
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