Abstract
A practical synthesis of 2'-deoxy-2'-fluoro-5-methyl-beta-L-arabinofuranosyl uracil (14, L-FMAU) was developed from L-arabinose. L-Arabinose was converted to L-ribose 5, which was used for the synthesis of bromosugar 12 via 2,3,5-O-tribenzoyl-1-O-acetyl-beta-L-ribofuranose 8, which was subjected to condensation with silylated thymine and the resulting protected L-FMAU 13 was deprotected to afford L-FMAU in 14 steps in 8% overall yield.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Antiviral Agents / chemical synthesis
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Arabinofuranosyluracil / analogs & derivatives*
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Arabinofuranosyluracil / chemical synthesis
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Arabinose / chemistry*
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Hepatitis, Viral, Human / drug therapy
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Nucleosides / chemical synthesis
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Nucleosides / therapeutic use
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Stereoisomerism
Substances
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Antiviral Agents
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Nucleosides
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Arabinofuranosyluracil
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Arabinose
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clevudine