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

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...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2012-03, Vol.44 (5), p.767-772
Main Authors: Sartori, Guillaume, Enderlin, Gérald, Hervé, Gwénaelle, Len, Christophe
Format: Article
Language:English
Subjects:
Carbohydrates. Nucleosides and nucleotides
Chemical Sciences
Chemistry
Exact sciences and technology
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Preparations and properties
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-0031-1289709