Carbasugar analogues of galactofuranose: α-O-linked derivatives
(English)Manuscript (preprint) (Other academic)
Using an indirect method, we have synthesised α-linked carbasugar analogues of galactofuranosides for the first time. Opening of a β-talo configured carbasugar 1,2-epoxide by alcohol nucleophiles under Lewis acidic conditions proceeded with very good regioselectivity to give α-talo configured C-1-substituted ethers with OH-2 free. Inversion of configuration at OH-2 by an oxidation–reduction sequence gave the α-galacto configured carbahexofuranose C-1 ethers. A carbadisaccharide corresponding to the Galf(α1→3)Manp substructure from Apodus deciduus galactomannan was synthesised to exemplify the method.
galactofuranose, galactofuranosides, alfa-linked, carbasugars, pseudodisaccharides, glycomimetics, etherification, regioselective
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-44211OAI: oai:DiVA.org:su-44211DiVA: diva2:360314