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Synthesis 2008(15): 2363-2368  
DOI: 10.1055/s-2008-1067166
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Synthesis of Phosphonate Derivatives of 1,2-Disubstituted Carbocyclic Purine Nucleosides with a Cyclopentane Ring

Pedro Besada*, María J. González Moa, Carmen Terán
Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, 36310 Vigo, Spain
Fax: +34(986)812262; e-Mail: pbes@uvigo.es;
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Publication History

Received 29 January 2008
Publication Date:
08 July 2008 (online)

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Abstract

The synthesis of phosphonate 1,2-disubstituted carbocyclic nucleosides with a cyclopentane ring is described following two different strategies: inclusion of the phosphonomethyl group before or after coupling of the carbocyclic moiety with the heterocyclic base. The diethyl [(trifluoromethanesulfonyl)oxy]methanephosphonate is the key phosphonylating agent for both the strategies.

Key words

nucleosides - phosphonates - carbocycles - Mitsunobu reaction

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