Abstract
A general and efficient approach was developed for the introduction of S-functionality at the C-5 position of cytosine and uracil nucleosides and their analogues. The key step is a palladium-catalyzed C-S coupling of the corresponding 5-bromo nucleoside derivative and alkyl thiol. The butyl 3-mercaptopropionate coupling products were further converted to the corresponding disulphides, the stable precursors of 5-mercaptopyrimidine nucleosides.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Chemistry, Organic / methods*
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Cytosine / chemical synthesis
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Cytosine / chemistry
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Disulfides / chemical synthesis
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Disulfides / chemistry
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Lamivudine / analogs & derivatives
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Lamivudine / chemistry
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Pyrimidine Nucleosides / chemical synthesis*
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Pyrimidine Nucleosides / chemistry*
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Thiouracil / chemical synthesis
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Thiouracil / chemistry
Substances
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Disulfides
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Pyrimidine Nucleosides
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Lamivudine
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Thiouracil
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Cytosine