THE METHYL 2-O- (BENZYLTHIO)CARBONYL DERIVATIVE AS A PRECURSOR TO PARTIAL ESTERS OF METHYL α-D-GLUCOPYRANOSIDE
Open Access
- 1 May 1963
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 41 (5), 1223-1230
- https://doi.org/10.1139/v63-170
Abstract
The utility of the thiocarbonyl group for blocking the C2 hydroxyl in methyl glucosides has been demonstrated. Methyl 2-O-(benzylthio)carbonyl-α-D-glucopyranoside has been synthesized in good yield and its structure proved. Use of this 2-O-thiocarbonyl derivative in conjunction with acid-labile blocking groups has permitted the first syntheses of the following esters of methyl α-D-glucopyranoside: 3-O-benzoyl-, 3,4-di-O-benzoyl-, and 3,4,6-tri-O-benzoyl-, and the crystalline 2-O-(p-toluene)sulphonate derivative of each.Keywords
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