title: Glucosylenamines as glycosyl acceptors: synthesis of gentiobiosylenamines.
abstract: The preparation of 2,3,4-tri-O-benzyl- (3), 2,3,4-tri-O-acetyl- (4), and 2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-6-O-trityl-beta- D-glucopyranosylamine (5) is described. The reaction of 3-5 with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide yields 2,3,4-tri-O-benzyl- (9), 2,3,4-tri-O-acetyl- (10), and 2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-6-O-(2,3,4,6-tet ra-O- acetyl-beta-D-glucopyranosyl)-beta-D-glucopyranosylamine (11), respectively. 2,3,4-Tri-O-benzyl- (6), 2,3,4-tri-O-acetyl- (7), and 2,3,4-tri-O- benzoyl-N-(2,2-diethoxycarbonylvinyl)-beta-D-glucopyranosylamine (8) are also described.
authors.affiliation: Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Spain.
authors.forename: J
authors.initials: J
authors.lastname: Fuentes Mota
authors.forename: J
authors.initials: J
authors.lastname: Fernández-Bolaños Guzmán
authors.forename: J M
authors.initials: JM
authors.lastname: García Fernández
authors.forename: W
authors.initials: W
authors.lastname: Moreda
authors.forename: C
authors.initials: C
authors.lastname: Ortiz
authors.forename: M A
authors.initials: MA
authors.lastname: Pradera
authors.forename: I
authors.initials: I
authors.lastname: Robina
authors.forename: C
authors.initials: C
authors.lastname: Welsh
mesh_terms: D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008969:Molecular Sequence Data
chemical_list: D004187:Disaccharides; C100052:gentiobiose; D005944:Glucosamine