Abstract
The target compounds were synthesized via the key intermediate carbohydrate 8, which was synthesized by first selectively protecting the 1'- and 2'-hydroxyl groups followed by selective tosylation of the 5'-hydroxyl group to obtain compound 3. The tosyl moiety was then replaced by a benzyl either to obtain 4. Compound 4 underwent Dess-Martin oxidation to afford the ketone 5. Compound 5 was subjected to Wittig olefination to afford the alkene 6 followed by regioselective hydroboration to obtain 7. Compound 7 was fully acetylated using acetic acid, acetic anhydride and sulfuric acid to obtain the key intermediate 8.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Acetylation
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Anti-HIV Agents / chemical synthesis
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Anti-HIV Agents / chemistry
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Anti-HIV Agents / pharmacology
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Antiviral Agents / chemical synthesis*
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Antiviral Agents / chemistry
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Antiviral Agents / pharmacology
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HIV-1 / drug effects
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Hepatitis B virus / drug effects
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Humans
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In Vitro Techniques
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Leukocytes, Mononuclear / drug effects
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Leukocytes, Mononuclear / virology
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Magnetic Resonance Spectroscopy
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Ribonucleosides / chemical synthesis*
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Ribonucleosides / chemistry
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Ribonucleosides / pharmacology
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Stereoisomerism
Substances
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Anti-HIV Agents
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Antiviral Agents
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Ribonucleosides