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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 of D-lyxo-C-nucleoside analogs.
Sallam, M A; Abdel Megid, S M; Townsend, L B.
Afiliación
  • Sallam MA; Department of Chemistry, Faculty of Science, Alexandria University, Egypt.
Carbohydr Res ; 330(1): 53-63, 2001 Jan 15.
Article en En | MEDLINE | ID: mdl-11217962
ABSTRACT
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-(alpha-D-lyxopyranosyl)-2-phenyl-2H-1,2,3-triazole (major component) and its beta-anomer, as well as 4-(alpha-D-lyxofuranosyl)-2H-1,2,3-triazole and its beta-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.
Asunto(s)
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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Nucleósidos Idioma: En Revista: Carbohydr Res Año: 2001 Tipo del documento: Article País de afiliación: Egipto
Buscar en Google
Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Nucleósidos Idioma: En Revista: Carbohydr Res Año: 2001 Tipo del documento: Article País de afiliación: Egipto