Synthesis and conformational studies of carrabiose and its 4'-sulphate and 2,4'-disulphate.
Methyl alpha-carrabioside (13), and its 4-sulphate (19) and 2,4-disulphate (20) have been synthesised via glycosylation of methyl 3,6-anhydro-2-O-benzyl-alpha-D-galactopyranoside with 2,3,6-tri-O-acetyl-4-O-benzyl-beta-D-galactopyranosyl bromide and subsequent partial or complete debenzylation, sulphation, and deprotection of the resulting disaccharide derivatives. Conformational studies have been carried out on 13, 19, and 20 on the basis of 1D and 2D 1H-n.m.r. spectroscopy and molecular mechanics calculations.
Parra
E
E
Grupo de Carbohidratos, Instituto de Quimica Orgánica, Madrid, Spain.
Caro
H N
HN
Jiménez-Barbero
J
J
Martín-Lomas
M
M
Bernabé
M
M
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002351:Carrageenan / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008969:Molecular Sequence Data; D012984:Software
C068275:methylcarrabioside; C068276:methylcarrabioside 4'-sulfate; C068277:methylcarrabioside 2,4'-disulfate; D002351:Carrageenan