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

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
330
Issue
1
Identifiers
DOI: 10.1016/s0008-6215(00)00251-2
Keywords
  • 2-Phenyl-2H-1
  • 2
  • 3-Triazoles
  • α- And β-D-Lyxopyranosyl-α- And β-D-Lyxofuranosyl-C-Nucleosides
  • Anomeric Configuration

Abstract

Abstract Dehydration of 4-( d- galacto-pentitol-1-yl)-2-phenyl-2 H-1,2,3-triazole with 20% methanolic sulfuric acid afforded the anomeric pairs of nucleosides, 4-(α- d-lyxopyranosyl)-2-phenyl-2 H-1,2,3-triazole (major component) and its β-anomer, as well as 4-(α- d-lyxofuranosyl)-2 H-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.

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