ChemInform Abstract: Synthesis of 5-Amino-4-cyano-1-imidazolyl 2-Deoxy-β-D- ribofuranoside by Photolysis of 2-Aza-2′-deoxyadenosine or Glycosylation.

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.