Glucosylenamines as glycosyl acceptors: synthesis of gentiobiosylenamines.
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.
Fuentes Mota
J
J
Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, Spain.
Fernández-Bolaños Guzmán
J
J
García Fernández
J M
JM
Moreda
W
W
Ortiz
C
C
Pradera
M A
MA
Robina
I
I
Welsh
C
C
D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D008969:Molecular Sequence Data
D004187:Disaccharides; C100052:gentiobiose; D005944:Glucosamine