Nucleosides. 115. Reaction of 3'-O-Mesylthymidine. Formation of 1-(3-Azido-2,3-dideoxy-β-D-threo-pentofuranosyl)thymine and Its Conversion into 6,3'-Imino-1-(2,3-dideoxy-β-D-threo-pentofuranosyl)thymine

Article abstract of DOI:10.1021/jo01304a026

Treatment of 5'-O-trityl-3'-O-mesylthymidine (3) with NaN3 in DMF at reflux gave 5'-O-trityl-3'-azido-3'-deoxythymidine (5) and 6,3'-imino-1-(5-O-trityl-3-deoxy-β-D-threo-pentofuranosyl)thymine (8).Compound 8 was formed from the 3'-azido-threo-pentofuranosylthymine derivative 6.A mechanism is proposed for the formation of 8 from 6.Also, the 6,5'-imino-bridged thymidine 18 was prepared.Conformational features of these imino-bridged nucleosides are discussed.