title: A study of the epoxidation of 6-deoxyhex-5-enopyranosides. 1,5-Dicarbonyl derivatives and novel synthetic routes to D-xylo-hexos-5-ulose and D-lyxo-hexos-5-ulose.
abstract: The work described deals with the isolation and characterization of epoxides from 6-deoxyhex-5-enopyranosides and preliminary exploration of their synthetic potential. Prolonged epoxidation reaction times led to their hydrolysis in situ and gave novel protected D-hexos-5-ulose derivatives (sugar 1,5-dicarbonyls). Some reactions of the hexos-5-uloses were studied, and in some cases septanoside (seven-membered-ring saccharide) derivatives were isolated. Novel routes to D-xylo-hexos-5-ulose and D-lyxo-hexos-5-ulose, of interest as intermediates in the synthesis and biosynthesis of inositols and aza sugars, are also described. The structures of the epoxides and novel hexos-5-uloses were established by NMR and X-ray crystallographic methods.
authors.affiliation: Department of Chemistry, Centre for Synthesis and Chemical Biology, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland.
authors.forename: Philomena M
authors.initials: PM
authors.lastname: Enright
authors.forename: Manuela
authors.initials: M
authors.lastname: Tosin
authors.forename: Mark
authors.initials: M
authors.lastname: Nieuwenhuyzen
authors.forename: Linda
authors.initials: L
authors.lastname: Cronin
authors.forename: Paul V
authors.initials: PV
authors.lastname: Murphy
mesh_terms: D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D006601:Hexoses / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism
chemical_list: D004852:Epoxy Compounds; D006601:Hexoses