Εμφάνιση απλής εγγραφής

dc.creatorTsoukala, E.en
dc.creatorManta, S.en
dc.creatorTzioumaki, N.en
dc.creatorAgelis, G.en
dc.creatorKomiotis, D.en
dc.date.accessioned2015-11-23T10:52:25Z
dc.date.available2015-11-23T10:52:25Z
dc.date.issued2008
dc.identifier10.1016/j.carres.2008.02.004
dc.identifier.issn0008-6215
dc.identifier.urihttp://hdl.handle.net/11615/34075
dc.description.abstractThe chemical synthesis of 1,2,4-tri-O-acetyl-3-deoxy-3-fluoro-5-thio-D-xylopyranose, 1,2,4,6-tetra-O-acetyl-3-deoxy-3 -fluoro-5-thio-alpha(-D-glucopyranose and their corresponding nucleosides of thymine is described. Treatment of 3-fluoro-5-S-acetyl-5-thio-D-xylofuranose, obtained by hydrolysis of the isopropylidene group of 3-fluoro-1,2-O-isopropylidene-5-S-acetyl-5-thio-D-xylofuranose, with methanolic ammonia and direct acetylation, led to triacetylated 3-deoxy-3-fluoro-5-thio-D-xylopyranose. Condensation of acetylated 3-fluoro-5-thio-D-xylopyranose with silylated thymine afforded the corresponding nucleoside. Selective benzoylation and direct methanesulfonylation of 3-fluoro-1,2-O-isopropylidene-alpha-D-glucofuranose gave the 6-O-benzoyl-5-O-methylsulfonyl derivative, which on treatment with sodium methoxide afforded the 5,6-anhydro derivative. Treatment of the latter with thiourea, followed by acetolysis, gave the 3-fluoro-5-S-acetyl-6-O-acetyl-1,2-O-isopropylidene-5-thio-alpha-D-glucofuranose. 3-Fluoro-5-S-acetyl-6-O-acetyl-5-thio-D-glucofuranose, obtained after hydrolysis of 5-thiofuranose isopropylidene, was treated with ammonia in methanol and directly acetylated, giving tetraacetylated 3-deoxy-3-fluoro-5-thio-alpha-D-glucopyranose. Condensation of the latter with silylated thymine afforded the desired 3-deoxy-3-fluoro-5-thio-beta-D-glucopyranonucleoside analogue. (c) 2008 Elsevier Ltd. All rights reserved.en
dc.sourceCarbohydrate Researchen
dc.source.uri<Go to ISI>://WOS:000255574200012
dc.subjectthiosugarsen
dc.subjectthionucleosidesen
dc.subject3-fluoro-5-thioxylopyranoseen
dc.subject3-fluoro-5-thio-glucopyranoseen
dc.subjectthymineen
dc.subjectFLUORO-KETOPYRANOSYL NUCLEOSIDESen
dc.subjectCONFORMATIONAL-ANALYSISen
dc.subjectBIOLOGICALen
dc.subjectEVALUATIONen
dc.subjectN-4-BENZOYL CYTOSINEen
dc.subjectANTITUMOR AGENTSen
dc.subjectDRUG-RESISTANCEen
dc.subjectTHIO-SUGARSen
dc.subjectMECHANISMen
dc.subject5-THIO-D-GLUCOSEen
dc.subjectPYRIMIDINESen
dc.subjectBiochemistry & Molecular Biologyen
dc.subjectChemistry, Applieden
dc.subjectChemistry, Organicen
dc.titleA concise synthesis of 3-fluoro-5-thio-xylo- and glucopyranoses, useful precursors towards their corresponding pyranonucleoside derivativesen
dc.typejournalArticleen


Αρχεία σε αυτό το τεκμήριο

ΑρχείαΜέγεθοςΤύποςΠροβολή

Δεν υπάρχουν αρχεία που να σχετίζονται με αυτό το τεκμήριο.

Αυτό το τεκμήριο εμφανίζεται στις ακόλουθες συλλογές

Εμφάνιση απλής εγγραφής