Synthesis of 5‐amino‐4‐cyano‐1‐imidazolyl 2‐Deoxy‐β‐D‐ribofuranoside by photolysis of 2‐aza‐2′‐deoxyadenosine or glycosylation
- 12 July 1991
- journal article
- research article
- Published by Wiley in European Journal of Organic Chemistry
- Vol. 1991 (7) , 695-697
- https://doi.org/10.1002/jlac.1991199101122
Abstract
The photolysis of 2‐aza‐2′‐deoxyadenosine (1) results in the formation of a single reaction product. Its structure was assigned as 5‐amino‐4‐cyano‐1‐imidazolyl 2‐deoxyribofuranoside (2). The latter is also obtained independently from the glycosylation of the 5‐amino‐4‐imidazolecarbonitrile (4) anion with the halogenose 5. The reaction is stereoselective but regioisomers are formed: the N‐1 compound 6 in 21% and the N‐3 regiosomer 7 in 45% yield. The structures of the regioisomeric imidazole nucleosides 2 and 3 have been assigned by 13C‐NMR and 1H‐NMR NOE difference spectroscopy.Keywords
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