title: Homo-C-nucleoside analogs IV. Synthesis of 4-(2,5-anhydro-D-altro-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole homo-C-nucleoside. CD assignment of the absolute configuration of the carbon bridge.
abstract: Dehydrative cyclization of 4-(D-altro-pentitol-1-yl)2-phenyl-2H-1,2,3-triazole in basic medium with one moler equivalent of p-toluene sulfonyl chloride in pyridine solution gave the homo-C-nucleoside 4-(2,5-anhydro-D-altro-1-yl)-2-phenyl-2H-1,2,3-triazole. The structure and anomeric configuration was determined by acylation, nuclear magnetic resonance (NMR), and mass spectroscopy. The stereochemistry at the carbon bridge of homo-C-nucleoside 2-phenyl-2H-1,2,3-triazoles was determined by circular dichroism (CD) spectroscopy.
authors.affiliation: Chemistry Department, Faculty of Science, Alexandria University, Alexandria, Egypt.
authors.forename: Mohammed A E
authors.initials: MA
authors.lastname: Sallam
mesh_terms: D002244:Carbon / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009705:Nucleosides; D011725:Pyridines; D014230:Triazoles; D002244:Carbon; C023666:pyridine
keywords: 1,2,3-triazoles; anomeric configuration; carbon bridge chirality; circular dichroism; homo-C-nucleosides