SYNTHESIS OF 5-AMINO-4-CYANO-1-IMIDAZOLYL 2-DEOXY-BETA-D-RIBOFURANOSIDE BY PHOTOLYSIS OF 2-AZA-2'-DEOXYADENOSINE OR GLYCOSYLATION

Autor(en): KAZIMIERCZUK, Z
SEELA, F
Stichwörter: 2'-DEOXYRIBONUCLEOSIDES; Chemistry; Chemistry, Multidisciplinary; GLYCOSYLATIONS; IMIDAZO[4,5-D]-1,2,3-TRIAZINE; IMIDAZOLE; NOE DIFFERENCE SPECTROSCOPY; NUCLEOBASE-ANION GLYCOSYLATION; PHOTOLYSIS
Erscheinungsdatum: 1991
Herausgeber: VCH PUBLISHERS INC
Journal: LIEBIGS ANNALEN DER CHEMIE
Ausgabe: 7
Startseite: 695
Seitenende: 697
Zusammenfassung: 
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 regioisomer 7 in 45% yield. The structures of the regioisomeric imidazole nucleosides 2 and 3 have been assigned by C-13-NMR and H-1-NMR NOE difference spectroscopy.
ISSN: 01702041

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