The utility of the thiocarbonyl group for blocking the Cz hydroxyl in methyl glucosides has been demonstrated. Methyl 2-0-(benzy1thio)carbonyl-a-D-glucopyranoside has been synthesized in good yield and its structure proved. Use of this 2-0-thiocarbonyl derivative in conjunction with acid-labile blocking groups has permitted the first syntheses of the following esters of methyl a-D-glucopyranoside: 3-0-benzoyl-, 3,4-di-0-benzoyl-, and 3,4,6-tri-0-benzoyl-, and the crqstalline 2-0-(p-to1uene)sulphonate derivative of each.
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