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Synthesis 2012(5): 767-772  
DOI: 10.1055/s-0031-1289709
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Effective Synthesis of C-5-Substituted 2′-Deoxyuridine Using Suzuki-Miyaura Cross-Coupling in Water

Guillaume Sartori, Gérald Enderlin, Gwénaelle Hervé, Christophe Len*
Transformations Intégrées de la Matière Renouvelable, UTC-ESCOM, Centre de recherche Royallieu, BP 20529, 60205 Compiègne, France
Fax: +33(3)44971591; e-Mail: christophe.len@utc.fr;
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Publikationsverlauf

Received 22 November 2011
Publikationsdatum:
14. Februar 2012 (online)

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Abstract

An efficient protocol to provide a series of C-5-substituted 2′-deoxyuridine derivatives using a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction in water has been established. Starting from 2′-deoxyuridine derivatives, the target nucleoside analogues were obtained in good yields with low levels of palladium loading without protection of any hydroxyl group of the glycone moiety.

Key words

cross-coupling - Suzuki-Miyaura - nucleosides - green chemistry

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