PRODUCTS FROM FURANS .7. A GENERAL-ROUTE FOR THE SYNTHESIS OF ALPHA-(1,2-CIS) AND BETA-(1,2-TRANS) GLYCOCONJUGATES VIA 1-O-ACYL AND 1-O-ETHOXYCARBONYL-2-AZIDO-2,3-DIDEOXYGLYCOPYRANOSIDES

dc.contributor.author	GEORGIADIS, MP	en
dc.contributor.author	COULADOUROS, EA	en
dc.date.accessioned	2014-06-06T06:41:59Z
dc.date.available	2014-06-06T06:41:59Z
dc.date.issued	1991	en
dc.identifier.issn	0022-152X	en
dc.identifier.uri	http://62.217.125.90/xmlui/handle/123456789/370
dc.subject.classification	Chemistry, Organic	en
dc.subject.other	DERIVATIVES	en
dc.subject.other	GLYCOSIDES	en
dc.subject.other	SUGARS	en
dc.subject.other	ACID	en
dc.subject.other	GLYCOPROTEINS	en
dc.title	PRODUCTS FROM FURANS .7. A GENERAL-ROUTE FOR THE SYNTHESIS OF ALPHA-(1,2-CIS) AND BETA-(1,2-TRANS) GLYCOCONJUGATES VIA 1-O-ACYL AND 1-O-ETHOXYCARBONYL-2-AZIDO-2,3-DIDEOXYGLYCOPYRANOSIDES	en
heal.type	journalArticle	en
heal.language	English	en
heal.publicationDate	1991	en
heal.abstract	A methodology for the synthesis of 2,3,6-trideoxy- and 2,3-dideoxy-2-aminoglycosides is presented. 2,3-Dideoxyhex-2-enopyranos-4-uloses (named also as 2H-pyran-3(6H)-Ones) were used for the synthesis of 1-O-acetyl, 1-O-ethyloxycarbonyl and 1-S-phenyl-2,3,6-trideoxy-(or 2,3-dideoxy)-2-azidoglycopyranosyl donors. Glycosidation of the above thio-ethers with a variety of alcohols in the presence of N-bromosuccinimide as activator yielded predominantly alpha-glycosides, while acetates afforded beta-glycosides when TMSOTf was used as a promoter. The coupling of carbonates using tin tetrachloride or TMSOTf proved to be the most successful procedure, yielding the beta-glycoside as the predominant product. Thus, glycoconjugates of aminosugars, steroids and aminoacids have been synthesized.	en
heal.publisher	HETERO CORPORATION	en
heal.journalName	JOURNAL OF HETEROCYCLIC CHEMISTRY	en
dc.identifier.issue	5	en
dc.identifier.volume	28	en
dc.identifier.isi	ISI:A1991HU84500026	en
dc.identifier.spage	1325	en
dc.identifier.epage	1337	en