title: Carbasugar analogues of galactofuranosides: α-O-linked derivatives.
abstract: Using an indirect method, we have synthesised α-linked carbasugar analogues of galactofuranosides for the first time. Ring 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 C1-substituted ethers with a free OH-group at the C2 position. Inversion of configuration at C2 by an oxidation-reduction sequence gave the α-galacto configured carbahexofuranose C1 ethers. A carbadisaccharide corresponding to the Galf(α1→3)Manp substructure from Apodus deciduus galactomannan was synthesised to exemplify the method.
authors.affiliation: Department of Organic Chemistry, The Arrhenius Laboratory, Stockholm University, Stockholm 106 91, Sweden.
authors.forename: Jens
authors.initials: J
authors.lastname: Frigell
authors.forename: Ian
authors.initials: I
authors.lastname: Cumpstey