Thio-oligosaccharides of sialic acid - Synthesis of an a(2→3) sialyl galactoside via a gulofuranose/galactopyranose approach

Turnbull, W. Bruce and Field, Robert A. ORCID: https://orcid.org/0000-0001-8574-0275 (2000) Thio-oligosaccharides of sialic acid - Synthesis of an a(2→3) sialyl galactoside via a gulofuranose/galactopyranose approach. Journal of the Chemical Society, Perkin Transactions 1 (12). pp. 1859-1866. ISSN 1470-4358

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Abstract

A new approach to the synthesis of thio-oligosaccharides containing the N-acetylneuraminic acid-α(2→3): galactopyranose linkage is described. 3-O(Trifluoromethylsulfbnyl)gulofuranpse derivative 5 can be converted into the α-2,3-sialyl-3-thiogalactofuranose derivative 8 in good yield. Partial deprotection of the thiodisaccharide provides an α/β mixture of both galactofurahose and galactopyranose isomers,'but this mixture can be transformed efficiently into the desired pyranose-ring form to allow further elaboration into other glycosides via trichloroacetimidate donor 21. This strategy avoids introducing sulfur into 3-O-(trifluoromethylsulfonyl)gulopyranose derivatives, which can be prone to elimination side reactions.

Item Type:	Article
Uncontrolled Keywords:	general chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1600
Faculty \ School:	Faculty of Science > School of Chemistry, Pharmacy and Pharmacology
Related URLs:	https://www.scopus.com/pages/publication...
Depositing User:	LivePure Connector
Date Deposited:	11 Sep 2024 09:30
Last Modified:	18 Jun 2026 20:21
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96685
DOI:	10.1039/B002319L

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