title: Formation of septanoses from hexopyranosides via 5,6-exo-glycals.
abstract: Methyl D-hexo-5-ulosides are obtained in high yield by dihydroxylation of 5,6-exo-glucal compounds. The bicyclic structure (1,6-anhydropyrano-5-ulose) of the products is adopted in solution and in solid state in a (4)C(1) conformation. This methodology has been used to prepare 1,6-anhydro-L-idopyrano-5-uloses. Further manipulation of the 1,6-anhydro bridge allowed the preparation of the yet unknown septano-5-uloses in moderate to high yields.
authors.affiliation: UMR 7565 SRSMC, Nancy Université-CNRS, Groupe SUCRES, BP 70239, F-54506 Nancy Vandœuvre, France.
authors.forename: Olivier
authors.initials: O
authors.lastname: Jackowski
authors.forename: Françoise
authors.initials: F
authors.lastname: Chrétien
authors.forename: Claude
authors.initials: C
authors.lastname: Didierjean
authors.forename: Yves
authors.initials: Y
authors.lastname: Chapleur
mesh_terms: D002384:Catalysis; D005947:Glucose / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D008698:Mesylates / Q000737:chemistry; D008958:Models, Molecular; D009942:Organometallic Compounds / Q000737:chemistry; D010100:Oxygen / Q000737:chemistry
chemical_list: D006027:Glycosides; D008698:Mesylates; D009942:Organometallic Compounds; C518808:ytterbium(III) triflate; D005947:Glucose; D010100:Oxygen