Carbasugar analogues of galactofuranosides: α-O-linked derivatives

Carbasugar analogues of galactofuranosides: α-O-linked derivatives

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 C...

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Bibliographic Details
Main Authors: Jens Frigell, Ian Cumpstey
Format: Article
Language:English
Published: Beilstein-Institut 2010-11-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
carbasugars
etherification
galactofuranose
glycomimetics
pseudodisaccharides
regioselective
Online Access:https://doi.org/10.3762/bjoc.6.129
Description
Summary: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.
ISSN:1860-5397

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