The potential of carbocyclic nucleosides for the treatment of AIDS: synthesis of carbocyclic 6′-fluoro-2′,3′-dideoxythymidine
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 10,p. 2373-2377
- https://doi.org/10.1039/p19910002373
Abstract
The carbocyclic nucleoside 4 and the corresponding triphosphate 5 were prepared from cyclopent-2-enylmethanol 6 in 8 and 10 steps respectively. The key step in the synthesis is the reaction of the azido alcohol 9 with diethylaminosulphur trifluoride: participation of the azido group led to the formation of the isomeric fluorides 10 and 11(ratio ca. 2:1). The triphosphate 5 was found to be a poor inhibitor of HIV-coded reverse transcriptase.Keywords
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