Synthesis 2007(12): 1890-1897  
DOI: 10.1055/s-2007-965976
PSP
© Georg Thieme Verlag Stuttgart · New York

Palladium-Catalyzed Alkynylation (Sonogashira Coupling) at C-5 of the Uracil Moiety in Modified Unsaturated Pyranosyl Nucleosides

Jr. Francisco J. B. Mendonçaa,b, Janaína V. dos Anjosa,c, Denis Sinou*a, Sebastiao J. de Melob, Rajendra M. Srivastava*c
a Laboratoire de Synthèse Asymétrique, UMR 5246-ICBMS, ESCPE Lyon, Université Claude Bernard Lyon 1, 43 boulevard du 11 Novembre 1918, 69622 Villeurbanne Cedex, France
Fax: 33(4)78898914; e-Mail: sinou@univ-lyon1.fr;
b Departamento de Antibióticos, Universidade Federal de Pernambuco, Cidade Universitária, 50670-901, Recife, PE, Brazil
c Departamento de Química Fundamental, Universidade Federal de Pernambuco, Cidade Universitária, 50740-540, Recife, PE, Brazil
Fax: 55 8121268440; e-Mail: rms@ufpe.br;
Further Information

Publication History

Received 25 January 2007
Publication Date:
12 March 2007 (online)

Abstract

Various unsaturated 4-(5-substituted-uracil-1-yl)glycopyranosides were synthesized in good yields by a palladium-catalyzed cross-coupling reaction of ethyl 6-O-(tert-butyldimethylsilyl)-2,3,4-trideoxy-4-[5-iodo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]-α-d-erythro-hex-2-enopyranoside with a range of acetylenic derivatives.