Abstract
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 Rf=0.6 [reported1 one spot at Rf=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.
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