Journal of Organic Chemistry p. 924 - 928 (1990)
Update date:2022-08-04
Topics:
Sekine, Mitsuo
Nakanishi, Takeshi
This paper deals with convenient synthesis of 3'-O-methylthymidine (2) and 3'-deoxythymidine (3), which involve Ag2O-promoted methylation and Barton-Robins reductive deoxygenation, respectively.New methods for the regioselective 3'- and 5'-deoxygenation of thymidine have also been developed.Namely, compound 3 was synthesized by the 3',5'-O-diacylation of thymidine with phenyl chlorothionoformate (PTCF) followed by the selective 3'-reduction with tributyltin hydride and successive alkaline hydrolysis. 5'-Deoxythymidine (18) was obtained by the 5'-selective acylation of thymidine with PTCF followed by reduction with tributyltin hydride.
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