Synthesis of 5鈥?Methylene-Phosphonate Furanonucleoside Prodrugs: Application to D-2鈥?Deoxy-2鈥?伪-fluoro-2鈥?尾-C-methyl Nucleosides
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- 作者：Ugo Pradere ; Franck Amblard ; Steven J. Coats ; Raymond F. Schinazi
- 刊名：Organic Letters
- 出版年：2012
- 出版时间：September 7, 2012
- 年：2012
- 卷：14
- 期：17
- 页码：4426-4429
- 全文大小：288K
- 年卷期：v.14,no.17(September 7, 2012)
- ISSN：1523-7052
文摘
A new and facile synthetic pathway to metabolically stable 5鈥?methylene-bis(pivaloyloxymethyl)(POM)phosphonate furanonucleoside prodrugs is reported. The key step involves a Horner鈥揥adsworth鈥揈mmons reaction of a tetra(pivaloyloxymethyl) bisphosphonate salt with appropriately protected 5鈥?aldehydic nucleosides. This efficient approach was applied for the synthesis HCV related 2鈥?deoxy-2鈥?伪-fluoro-2鈥?尾-C-methyl nucleosides.