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Synthesis 2006(3): 467-470  
DOI: 10.1055/s-2006-926280
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Very Simple Synthesis of 1-(Ethyl 6-O-Acetyl-2,3,4-trideoxy-α-d-erythro-hex-2-enopyranos-4-yl)-1,2,3-triazole Derivatives

Ronaldo N. de Oliveiraa,b, Denis Sinou*a, Rajendra M. Srivastava*b
a Laboratoire de Synthèse Asymétrique, UMR 5181, ESCPE Lyon, Université Claude Bernard Lyon1, 43 boulevard du 11 Novembre 1918, 69662, Villeurbanne Cedex, France
Fax: +33(4)78898914; e-Mail: sinou@univ-lyon1.fr;
b Departamento de Quimica Fundamental, Universidade Federal de Pernambuco, Cidade Universitaria, 50740-540, Recife, PE, Brazil
Further Information

Publication History

Received 25 July 2005
Publication Date:
11 January 2006 (online)

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Abstract

The copper-catalyzed reaction of ethyl 4-azido-6-O-acetoxy-2,3,4-trideoxy-α-d-erythro-hex-2-enopyranoside with various functionalized alkynes gave the corresponding 1-(ethyl 6-O-acetyl-2,3,4-trideoxy-α-d-erythro-hex-2-enopyranos-4-yl)-1,2,3-triazole derivatives in quite good yields, which could be transformed into (ethyl 2,3,6-tri-O-acetyl-4-deoxy-α-d-mannopyranosyl)-1H-1,2,3-triazole by a simple bis-hydroxylation.

Key words

1,2,3-triazole based-carbohydrate - hexenopyranoside - cycloaddition - Cu catalyst

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de Oliveira, R. N.; Cottier, L.; Sinou, D.: Srivastava, R. M. Tetrahedron 2005, 61, 8271.