Synthesis of hypoxanthine, guanine, and 6-thiopurine nucleosides of 6-deoxy-D-allofuranose

V Nelson, HS El Khadem, BK Whitten…

Index: Nelson; El Khadem; Whitten; Sesselman Journal of Medicinal Chemistry, 1983 , vol. 26, # 7 p. 1071 - 1074

Full Text: HTML

Citation Number: 15

Abstract

In order to determine the anomeric configuration of nucleosides, NMR coupling constant of the H-1'proton is commonly used. However, all four of our compounds show a doublet for this proton with J= 6-7 Hz, consistent with either an a or P configuration. 1 A rule by Bakerll states that sugar derivatives with an ester group at C-2'will give rise to only 1, 2-trans nucleosides. Although exceptions are known, 12 this rule seems to have held true in our ...