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Synthesis of 5-amino-4-cyano-1-imidazolyl 2-Deoxy-β-D-ribofuranoside by photolysis of 2-aza-2′-deoxyadenosine or glycosylation

✍ Scribed by Kazimierczuk, Zygmunt ;Seela, Frank

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
274 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

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 ^13^C‐NMR and ^1^H‐NMR NOE difference spectroscopy.

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