Facile Synthesis of 3'-O-Methylthymidine and 3'-Deoxythymidine and Related Deoxygenated Thymidine Derivative: A New Method for Selective Deoxygenation of Secondary Hydroxy Groups

Article abstract of DOI:10.1021/jo00290a024

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.