Facile synthesis of 2-(β- C-glucopyranosyl)-β-amino acid: a new class of glycopeptide building block

Facile synthesis of 2-(β- C-glucopyranosyl)-β-amino acid: a new class of glycopeptide building block

A convenient preparation of both stereoisomers of a (2 R)/(2 S)-2- C-glycosylated β-amino acid is described. β- C-Glycoside was formed by the reaction of α-acetobromoglucose with carbanion of cyanoacetate. The steric bulk of the C-glycoside moiety does not hinder amino acid coupling, showing the uti...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 48; no. 6; pp. 993 - 997
Main Authors: Inaba, Yoko, Yano, Shigenobu, Mikata, Yuji
Format: Journal Article
Language:English
Published: Elsevier Ltd 05-02-2007
Online Access:Get full text
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Summary:A convenient preparation of both stereoisomers of a (2 R)/(2 S)-2- C-glycosylated β-amino acid is described. β- C-Glycoside was formed by the reaction of α-acetobromoglucose with carbanion of cyanoacetate. The steric bulk of the C-glycoside moiety does not hinder amino acid coupling, showing the utility of this carbohydrate-containing building block for glycopeptide synthesis.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2006.12.006