Helvetica Chimica Acta p. 169 - 178 (1996)
Update date:2022-08-03
Topics: Synthesis Column chromatography NMR spectroscopy Reagents Catalyst Nucleophilic substitution 6-substituted
Wenzel
Seela
The synthesis of 6-substituted 1-deazapurine 2'-deoxyribonucleosides is described. Glycosylation of the 1-deazapurine (imidazo[4,5-b]pyridine) anions with the α-D-halogenose 5 gives stereoselectively N7- and N9-regioisomers. 1H-NMR NOE and 13C-NMR spectroscopy are used for unambiguous assignment of isomers, and 15N-NMR chemical shifts are correlated with σ(para) Hammett constants and point charges.
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Doi:10.1021/jp026641t
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