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Issue 30, 2014
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A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues

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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.

Graphical abstract: A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues

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Submitted
19 Mar 2014
Accepted
11 Jun 2014
First published
11 Jun 2014

Org. Biomol. Chem., 2014,12, 5634-5644
Article type
Paper
Author version available

A general approach to the synthesis of 5-S-functionalized pyrimidine nucleosides and their analogues

D. G. Kananovich, A. Reino, K. Ilmarinen, M. Rõõmusoks, M. Karelson and M. Lopp, Org. Biomol. Chem., 2014, 12, 5634
DOI: 10.1039/C4OB00597J

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