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Molecules 2018, 23(6), 1457; https://doi.org/10.3390/molecules23061457

Phosphorus Pentachloride Promoted gem-Dichlorination of 2′- and 3′-Deoxynucleosides

Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Herestraat 49, 3000 Leuven, Belgium
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Academic Editor: Christian Ducho
Received: 29 May 2018 / Revised: 11 June 2018 / Accepted: 11 June 2018 / Published: 15 June 2018
(This article belongs to the Special Issue Bioactive Nucleosides and Nucleotides)
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Abstract

Halogen substitution at various positions of canonical nucleosides has generated a number of bioactive structural variants. Herein, the synthesis of two unique series of sugar modified nucleosides bearing a gem-dichloro group is presented. The synthetic plan entails the controlled addition of phosphorus pentachloride to suitably protected 2′- or 3′-ketodeoxynucleoside intermediates as the key step, facilitating the rapid construction of such functionalized molecules. Under the same reaction conditions, the highest chemoselectivity was observed for the formation of 2′,2′-dichloro-2′,3′-dideoxynucleosides, while a competing 2′,3′-elimination process occurred in the case of the 3′,3′-dichloro counterparts. View Full-Text
Keywords: gem-dichlorination; modified nucleosides; halogenated nucleosides; phosphorus pentachloride gem-dichlorination; modified nucleosides; halogenated nucleosides; phosphorus pentachloride
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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da Paixao Soares, F.; Groaz, E.; Herdewijn, P. Phosphorus Pentachloride Promoted gem-Dichlorination of 2′- and 3′-Deoxynucleosides. Molecules 2018, 23, 1457.

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