title: Highly stereoselective synthesis of C-vinyl furanosides through acid-catalyzed S(N)2 inversion at the C-3 position of 1,2-dideoxy-hept-1-enitols.
abstract: A highly stereoselective synthesis of C-vinyl furanosides through the S(N)2 inversion at the C-3 position of the 1,2-dideoxy-hept-1-enitols is disclosed. Treatment of the 1,2-dideoxy-hept-1-enitols with diphenylammonium trifluoromethanesulfonate as the acid catalyst produced the C-vinyl furanosides (3,6-anhydro-1,2-dideoxy-hept-1-enitol derivatives) via a subsequent S(N)2 intramolecular debenzyloxyation-cycloetherification reaction at the C-3 position.
authors.affiliation: School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan.
authors.forename: Hitoshi
authors.initials: H
authors.lastname: Tsuchiya
authors.forename: Noriaki
authors.initials: N
authors.lastname: Asakura
authors.forename: Yasunori
authors.initials: Y
authors.lastname: Ikeda
authors.forename: Hidetoshi
authors.initials: H
authors.lastname: Yamada
mesh_terms: D002236:Carbohydrate Conformation; D002384:Catalysis; D050113:Imino Furanoses / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000737:chemistry*; D013816:Thermodynamics; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D050113:Imino Furanoses; D007202:Indicators and Reagents; D013402:Sugar Alcohols; D014753:Vinyl Compounds