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.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Amides / chemistry
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Amides / pharmacology
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Antiviral Agents / chemical synthesis
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Hepacivirus / drug effects*
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Methane / analogs & derivatives
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Molecular Structure
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Nucleosides / chemical synthesis*
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Nucleosides / chemistry
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Nucleosides / pharmacology
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Phosphoric Acids / chemistry
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Phosphoric Acids / pharmacology
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Prodrugs / chemical synthesis*
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Prodrugs / chemistry
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Prodrugs / pharmacology
Substances
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Amides
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Antiviral Agents
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Nucleosides
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Phosphoric Acids
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Prodrugs
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carbene
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phosphoramidic acid
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Methane