Key indicators: single-crystal X-ray study; T = 200 K; mean (C-C) = 0.003 Å; R factor = 0.036; wR factor = 0.095; data-to-parameter ratio = 13.0.In the crystal structure of the title compound, C 4 H 8 N 2 O 4 Á-C 18 H 15 OP, two triphenylphosphine oxide molecules and two dimethyl hydrazine-1,2-dicarboxylate molecules are connected via N-HÁ Á ÁO hydrogen bonds of moderate strength and are related via a twofold rotational axis. Weak C ar -HÁ Á Á O contacts strengthen the crystal structure.
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ExperimentalCrystal data
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.
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