J. J. Willard, J. Sadowski, W. Vitale
May 1, 1963
Citations
0
Influential Citations
23
Citations
Journal
Canadian Journal of Chemistry
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.