Synthesis of 6-substituted 1-deazapurine 2'-deoxyribonucleosides

Autor(en): Wenzel, T
Seela, F
Stichwörter: 1-DEAZAADENOSINE; BUILDING-BLOCKS; CHEMICAL SYNTHESIS; Chemistry; Chemistry, Multidisciplinary; INHIBITORS; POTENTIAL ANTI-METABOLITES; RIBONUCLEOSIDES
Erscheinungsdatum: 1996
Herausgeber: NEW SWISS CHEMICAL SOC
Journal: HELVETICA CHIMICA ACTA
Volumen: 79
Ausgabe: 1
Startseite: 169
Seitenende: 178
Zusammenfassung: 
The synthesis of 6-substituted 1-deazapurine 2'-deoxyribonucleosides is described. Glycosylation of the 1-deazapurine (imidazo[4,5-b]pyridine) anions with the alpha-D-halogenose 5 gives stereoselectively N-7- and N-9-regioisomers. H-1-NMR NOE and C-13-NMR spectroscopy are used for unambiguous assignment of isomers, and N-15-NMR chemical shifts are correlated with sigma(para) Hammett constants and point charges.
ISSN: 0018019X
DOI: 10.1002/hlca.19960790117

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