A Reinvestigation of the Dichlorination of Thymidine
- 1 January 1980
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 10 (9) , 685-688
- https://doi.org/10.1080/00397918008065650
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.Keywords
This publication has 3 references indexed in Scilit:
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- Improved Syntheses of ChlorodeoxynucleosidesSynthetic Communications, 1976
- Halo sugar nucleosides. III. Reactions for the chlorination and bromination of nucleoside hydroxyl groupsThe Journal of Organic Chemistry, 1972