Acid-catalyzed dehydrative cyclization of 4-(d-galacto-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole. Synthesis and anomeric configuration of d-lyxo-C-nucleoside analogs Original Research Article

Dehydration of 4-(d-galacto-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole with 20% methanolic sulfuric acid afforded the anomeric pairs of nucleosides, 4-(α-d-lyxopyranosyl)-2-phenyl-2H-1,2,3-triazole (major component) and its β-anomer, as well as 4-(α-d-lyxofuranosyl)-2H-1,2,3-triazole and its β-anomer. The four anomeric C-nucleosides were separated by chromatography, and their structure and anomeric configuration were determined by periodate oxidation, acylation, and NMR spectroscopy as well as mass spectrometry. The anomeric assignment from optical rotation was not in agreement with final structure assignment and represented a violation of the Hudson isorotation rules. NOE studies and X-ray diffraction measurements confirmed the anomeric configuration.