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Abstract

Reaction of 6-azauridine (I) with a mixture of thionyl chloride and hexamethylphosphoramide afforded 5'-chloro-5'-deoxy-6-azauridine (II) and a mixture of SR- and SS-isomers of 5'-chloro-5'-deoxy-2',3'-O-sulfinyl-6-azauridine (IIIa and IIIb) which were separated by column chromatography on silica gel; compounds IIIa and IIIb also arose in the reaction of compound II with diphenyl sulfite. Removal of the cyclic sulfinyl group from the isomeric sulfites IIIa and IIIb gave compound II; reaction of IIIa and IIIb with imidazole in dimethylformamide afforded the 5'-chloro-5'-deoxy-2,2'-anhydro derivative IV.