Molecules, Vol. 23, Pages 1457: Phosphorus Pentachloride Promoted gem-Dichlorination of 2 ′- and 3′-Deoxynucleosides

Molecules, Vol. 23, Pages 1457: Phosphorus Pentachloride Promoted gem-Dichlorination of 2′- and 3′-Deoxynucleosides
Molecules doi: 10.3390/molecules23061457
Authors:
Fabio da Paixao Soares
Elisabetta Groaz
Piet Herdewijn

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.

Source: Molecules - June 15, 2018 Category: Chemistry Authors: Fabio da Paixao Soares Elisabetta Groaz Piet Herdewijn Tags: Article Source Type: research