THE METHYL 2-O- (BENZYLTHIO)CARBONYL DERIVATIVE AS A PRECURSOR TO PARTIAL ESTERS OF METHYL α-D-GLUCOPYRANOSIDE

Autor:	J. J. Willard, Joanne Sadowski, William Vitale
Rok vydání:	1963
Předmět:	chemistry.chemical_compound chemistry Stereochemistry Yield (chemistry) Organic Chemistry General Chemistry Catalysis Derivative (chemistry)
Zdroj:	Canadian Journal of Chemistry. 41:1223-1230
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v63-170
Popis:	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.
Databáze:	OpenAIRE
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