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Synthesis 2004(14): 2335-2341  
DOI: 10.1055/s-2004-831190
PAPER
© Georg Thieme Verlag Stuttgart · New York

Lipophilic Nucleosides by Sonogashira Coupling

Wolfgang Flaschea, Crina Cismasa, Andreas Herrmannb, Jürgen Liebscher*a
a Institut für Chemie, Humboldt-Universität Berlin, Brook-Taylor-Str. 2, 12489 Berlin, Germany
Fax: +49(30)20937552; e-Mail: liebscher@chemie.hu-berlin.de;
b Institut für Biologie, Humboldt-Universität Berlin, Invalidenstr. 43, 10115 Berlin, Germany
Further Information

Publication History

Received 30 January 2004
Publication Date:
25 August 2004 (online)

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Abstract

New amphiphilic nucleosides 3, 5, 7, 9 and nucleobases 12, 14, with lipophilic alkynyl substituents attached to the N-heterocyclic ring were obtained in a straightforward manner by Sonoga­shira coupling of 5-iodouridine, 8-bromoadenosine and protected 8-bromoguanosine or related halonucleobases. In most cases protective groups were unnecessary.

Key words

nucleosides - nucleobases - cross-coupling - amphiphile - alkynes

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Full details have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 228985. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK.