Carbasugar analogues of galactofuranosides: beta-O-linked derivatives and towards beta-S-linked derivatives
2011 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 346, no 11, 1277-1290 p.Article in journal (Refereed) Published
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.
Carbasugars, Galactofuranose, Pseudodisaccharides, Glycomimetics, Ring-closing metathesis, Epoxide-opening
IdentifiersURN: urn:nbn:se:su:diva-68293DOI: 10.1016/j.carres.2011.04.032ISI: 000292858600002OAI: oai:DiVA.org:su-68293DiVA: diva2:477974
authorCount :32012-01-152012-01-032012-01-15Bibliographically approved