Carbasugar analogues of galactofuranosides: alpha-O-linked derivatives
2010 (English)In: BEILSTEIN J ORG CHEM, ISSN 1860-5397, Vol. 6, 1127-1131 p.Article in journal (Refereed) Published
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.
carbasugars, etherification, galactofuranose, glycomimetics, pseudodisaccharides, regioselective
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-51222DOI: 10.3762/bjoc.6.129ISI: 000284685500001OAI: oai:DiVA.org:su-51222DiVA: diva2:387798
FunderSwedish Research Council
authorCount :22011-01-142011-01-102011-01-20Bibliographically approved