SYNTHESIS OF 6-SUBSTITUTED 1-DEAZAPURINE 2'-DEOXYRIBONUCLEOSIDES

Authors
WENZEL T SEELA F
Citation
T. Wenzel et F. Seela, SYNTHESIS OF 6-SUBSTITUTED 1-DEAZAPURINE 2'-DEOXYRIBONUCLEOSIDES, Helvetica Chimica Acta, 79(1), 1996, pp. 169-178
Citations number
26
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
79
Issue
1
Year of publication
1996
Pages
169 - 178
Database
ISI
SICI code
0018-019X(1996)79:1<169:SO612>2.0.ZU;2-L
Abstract
The synthesis of 6-substituted 1-deazapurine 2'-deoxyribonucleosides i s described. Glycosylation of the 1-deazapurine (imidazo[4,5-b]pyridin e) anions with the alpha-D-halogenose 5 gives stereoselectively N-7- a nd N-9-regioisomers. H-1-NMR NOE and C-13-NMR spectroscopy are used fo r unambiguous assignment of isomers, and N-15-NMR chemical shifts are correlated with sigma(para) Hammett constants and point charges.