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A new method for the synthesis of 4'-substituted 4'-thiothymidines has been developed. This synthetic method consists of 1) diacetoxylation of 4',5'-unsaturated 4'-thiothymidine derivative 9 with Pb(OAc)(4), and 2) Lewis acid-promoted nucleophilic substitution of the resulting 4'-acetoxy nucleoside 10 with silicon reagents. This novel method enabled us to introduce carbon-substituents or heteroatom-substituents to the 4'-position.

Nucleophilic substitution of 4′-acetoxy-4′-thionucleosides: A new access to 4′-substituted 4′-thiothymidines