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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.

SUBMITTER: Frigell J

PROVIDER: S-EPMC3001987 | biostudies-literature | 2010 Nov

REPOSITORIES: biostudies-literature

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Carbasugar analogues of galactofuranosides: α-O-linked derivatives.

Frigell Jens J Cumpstey Ian I

Beilstein journal of organic chemistry 20101129

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 carbadisa ...[more]

PMID: 21160556

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