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

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 -dichloro group is presented. The synthetic plan entails the controlled addition of phosphoru...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2018-06, Vol.23 (6), p.1457
Main Authors: da Paixao Soares, Fabio, Groaz, Elisabetta, Herdewijn, Piet
Format: Article
Language:English
Subjects:
Cell culture
Chlorides - chemistry
Chlorine
Chromatography
Crystallography, X-Ray
gem-dichlorination
halogenated nucleosides
Halogens - chemistry
HIV
Human immunodeficiency virus
Intermediates
modified nucleosides
Molecular Structure
Nucleosides
Nucleosides - chemistry
Phosphorus
Phosphorus Compounds - chemistry
phosphorus pentachloride
Respiratory syncytial virus
Substitution reactions
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Summary: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 -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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules23061457