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

DC FieldValueLanguage
dc.contributor.authorKAZIMIERCZUK, Z
dc.contributor.authorSEELA, F
dc.date.accessioned2021-12-23T15:56:48Z-
dc.date.available2021-12-23T15:56:48Z-
dc.date.issued1991
dc.identifier.issn01702041
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/2541-
dc.description.abstractThe 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.
dc.language.isoen
dc.publisherVCH PUBLISHERS INC
dc.relation.ispartofLIEBIGS ANNALEN DER CHEMIE
dc.subject2'-DEOXYRIBONUCLEOSIDES
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectGLYCOSYLATIONS
dc.subjectIMIDAZO[4,5-D]-1,2,3-TRIAZINE
dc.subjectIMIDAZOLE
dc.subjectNOE DIFFERENCE SPECTROSCOPY
dc.subjectNUCLEOBASE-ANION GLYCOSYLATION
dc.subjectPHOTOLYSIS
dc.titleSYNTHESIS OF 5-AMINO-4-CYANO-1-IMIDAZOLYL 2-DEOXY-BETA-D-RIBOFURANOSIDE BY PHOTOLYSIS OF 2-AZA-2'-DEOXYADENOSINE OR GLYCOSYLATION
dc.typenote
dc.identifier.isiISI:A1991FY99200010
dc.description.issue7
dc.description.startpage695
dc.description.endpage697
dc.publisher.place303 NW 12TH AVE, DEERFIELD BEACH, FL 33442-1788
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