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Literature DB >> 22917194

Synthesis of 5'-methylene-phosphonate furanonucleoside prodrugs: application to D-2'-deoxy-2'-α-fluoro-2'-β-C-methyl nucleosides.

Ugo Pradere¹, Franck Amblard, Steven J Coats, Raymond F Schinazi.

Abstract

A new and facile synthetic pathway to metabolically stable 5'-methylene-bis(pivaloyloxymethyl)(POM)phosphonate furanonucleoside prodrugs is reported. The key step involves a Horner-Wadsworth-Emmons reaction of a tetra(pivaloyloxymethyl) bisphosphonate salt with appropriately protected 5'-aldehydic nucleosides. This efficient approach was applied for the synthesis HCV related 2'-deoxy-2'-α-fluoro-2'-β-C-methyl nucleosides.

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Year: 2012 PMID： 22917194 PMCID： PMC3470451 DOI： 10.1021/ol301937v

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

23 in total

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Journal: Nat Rev Drug Discov Date: 2005-11 Impact factor: 84.694

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Journal: J Med Chem Date: 2005-08-25 Impact factor: 7.446

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Authors: P Ioannidis; B Classon; B Samuelsson; I Kvarnström
Journal: Acta Chem Scand Date: 1991-08

6. Synthesis of acyloxymethyl ester prodrugs of the transferable protein farnesyl transferase substrate farnesyl methylenediphosphonate.

Authors: Jerry M Troutman; Kareem A H Chehade; Katarzyna Kiegiel; Douglas A Andres; H Peter Spielmann
Journal: Bioorg Med Chem Lett Date: 2004-10-04 Impact factor: 2.823

7. A simple and advantageous protocol for the oxidation of alcohols with O-iodoxybenzoic acid (IBX).

Authors: Jesse D More; Nathaniel S Finney
Journal: Org Lett Date: 2002-08-22 Impact factor: 6.005

Review 8. Nucleoside, nucleotide, and non-nucleoside inhibitors of hepatitis C virus NS5B RNA-dependent RNA-polymerase.

Authors: Michael J Sofia; Wonsuk Chang; Phillip A Furman; Ralph T Mosley; Bruce S Ross
Journal: J Med Chem Date: 2012-01-23 Impact factor: 7.446

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Journal: Nat Rev Microbiol Date: 2004-09 Impact factor: 60.633

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Authors: Yung-hyo Koh; Jae Hoon Shim; Jim Zhen Wu; Weidong Zhong; Zhi Hong; Jean-Luc Girardet
Journal: J Med Chem Date: 2005-04-21 Impact factor: 7.446

3 in total