Journal of Organic Chemistry p. 3274 - 3278 (1980)
Update date:2022-07-29
Topics:
Matsuda, Akira
Watanabe, Kyoichi A.
Fox, Jack J.
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.
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