A Reinvestigation of the Dichlorination of Thymidine

Abstract

The reaction of thymidine with thionyl chloride in HMPA, reported¹ to give pure 1-(3,5-dichloro-2,3,5-trideoxy-β-D-threo-pentofuranosyl)thymine, has been found to give a mixture of erythro and threo isomers. Upon reacting thymidine with thionyl chloride, according to the literature procedure,¹ a product was isolated which melted 138–141°C [reported¹ 138–140°C] and gave one spot in CHCl₃/ETOH (4:1) on Eastman silica gel sheets at R_f=0.6 [reported¹ one spot at R_f=0.7 on Baker silica gel sheets]. However, the TLC of the product in neat ethyl acetate or CHCl₃/MeOH (9:1) gave two spots. A sample was separated into pure components by flash chromatography².