Reaction of nucleosides with thionyl chloride; preparation of the deoxy derivatives of cytidine and adenosine

H Hřebabecký, J Brokeš, J Beránek

Index: Hrebabecky, Hubert; Brokes, Josef; Beranek, Jiri Collection of Czechoslovak Chemical Communications, 1980 , vol. 45, # 2 p. 599 - 605

Full Text: HTML

Citation Number: 17

Abstract

Abstract On reaction of thionyl chloride with cytidine and adenosine in refluxing acetonitrile, the 5'-chloro-2', 3'-sulphinyl derivatives I and VII are formed in a quantitative yield. On heating in dimethyl-formamide, compound I affords 5'-chloro-5'-deoxycyclocytidine (II) which is hydrolyzed in alkali to the arabinosyl derivative III; reduction of III with tributyltin hydride gives the 5'-deoxyarabinosyl derivative IV. The sulphinyl derivative I is hydrolyzed to 5'- ...