THIOCARBONATES AS BLOCKING GROUPS FOR THE SYNTHESIS OF PARTIAL ESTERS OF CARBOHYDRATES

Autor:	J. J. Willard
Rok vydání:	1962
Předmět:	chemistry.chemical_compound Ester derivatives Chemistry Acetylation Organic Chemistry Pyridine Organic chemistry Thiocarbonate General Chemistry Carbonyl group Catalysis Derivative (chemistry)
Zdroj:	Canadian Journal of Chemistry. 40:2035-2040
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v62-313
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::9a2eb8be1b95b007734d016cf56fed45 https://doi.org/10.1139/v62-313 Zobrazit plný text záznamu