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Carbasugar analogues of galactofuranosides: beta-O-linked derivatives and towards beta-S-linked derivatives
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
Stockholm University, Faculty of Science, Department of Organic Chemistry.
2011 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 346, no 11, 1277-1290 p.Article in journal (Refereed) Published
Abstract [en]

A selectively protected carbasugar analogue of beta-galactofuranose was synthesised from glucose using ring-closing metathesis as the key step. The carbasugar was converted into an alpha-galacto configured 1,2-epoxide, which was an effective electrophile in Lewis acid catalysed coupling reactions with alcohols. The epoxide was opened with regioselective attack at C-1 to give beta-galacto configured C-1 ethers. Using carbohydrates as nucleophiles, we synthesised a number of pseudodisaccharides. The epoxide was also regioselectively opened at C-1 with a sulfur nucleophile under basic conditions to give a beta-galacto configured C-1 thioether.

Place, publisher, year, edition, pages
2011. Vol. 346, no 11, 1277-1290 p.
Keyword [en]
Carbasugars, Galactofuranose, Pseudodisaccharides, Glycomimetics, Ring-closing metathesis, Epoxide-opening
National Category
Natural Sciences
Identifiers
URN: urn:nbn:se:su:diva-68293DOI: 10.1016/j.carres.2011.04.032ISI: 000292858600002OAI: oai:DiVA.org:su-68293DiVA: diva2:477974
Note
authorCount :3Available from: 2012-01-15 Created: 2012-01-03 Last updated: 2017-12-08Bibliographically approved

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