133349-83-4Relevant academic research and scientific papers
Synthesis of 5-Amino-4-cyano-1-imidazolyl 2-Deoxy-β-D-ribofuranoside by Photolysis of 2-Aza-2'-deoxyadenosine or Glycosylation
Kazimierczuk, Zygmunt,Seela, Frank
, p. 695 - 698 (2007/10/02)
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 percent and the N-3 regioisomer 7 in 45 percent yield.The structures of the regioisomeric imidazole nucleosides 2 and 3 have been assigned by 13C-NMR and 1H-NMR NOE difference spectroscopy. Key words: Imidazo-1,2,3-triazine / Imidazole / 2'-Deoxyribonucleosides / Nucleobase-anion glycosylation / Photolysis / Glycosylations
