Syntheses of <scp>d</scp>-Arabinofuranosyl and 2′-Deoxy-<scp>d</scp>-ribofuranosyl 1,2,3-Triazolecarboxamides

Abstract

Abstract Several d-arabino- and 2′-deoxy-d-ribonucleosides of 1,2,3-triazolecarboxamides were synthesized by two methods, one involving acid-catalyzed fusion reactions of 1-O-acetyl derivatives (3, 5) of the corresponding sugars and 1,2,3-triazole-4-carboxylate (1), and the other by glycosylation of the trimethylsilyl derivative (2) of 1 with glycosyl halides (4, 6). Evidence for the N-glycosylation sites and anomeric configurations of the resulting nucleosides is presented.