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Carbasugar analogues of galactofuranosides: alpha-O-linked derivatives
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2010 (English)In: BEILSTEIN J ORG CHEM, ISSN 1860-5397, Vol. 6, 1127-1131 p.Article in journal (Refereed) Published
Abstract [en]

Using an indirect method, we have synthesised alpha-linked carbasugar analogues of galactofuranosides for the first time. Ring opening of a beta-talo configured carbasugar 1,2-epoxide by alcohol nucleophiles under Lewis acidic conditions proceeded with very good regioselectivity to give alpha-talo configured C1-substituted ethers with a free OH-group at the C2 position. Inversion of configuration at C2 by an oxidation-reduction sequence gave the alpha-galacto configured carbahexofuranose C1 ethers. A carbadisaccharide corresponding to the Galf(alpha 1 -> 3)Manp substructure from Apodus deciduus galactomannan was synthesised to exemplify the method.

Place, publisher, year, edition, pages
2010. Vol. 6, 1127-1131 p.
Keyword [en]
carbasugars, etherification, galactofuranose, glycomimetics, pseudodisaccharides, regioselective
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-51222DOI: 10.3762/bjoc.6.129ISI: 000284685500001OAI: oai:DiVA.org:su-51222DiVA: diva2:387798
Funder
Swedish Research Council
Note
authorCount :2Available from: 2011-01-14 Created: 2011-01-10 Last updated: 2011-01-20Bibliographically approved

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