[Synthesis of 2-acetamido-2-deoxy-4-O-alpha-L-fucopyranosyl-alpha-D-glucopyranose].
Condensation of 2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl bromide with benzyl 2-acetamido-3,6-di-O-benzyl-alpha-D-glucopyranoside in dichloromethane-N,N-dimethylformamide, in the presence of tetraethylammonium bromide, diisopropylethylamine, and molecular sieve (halide ion-catalyzed reaction), gave benzyl 2-acetamido-3,6-di-O-benzyl-2 deoxy-4-O-(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)-alpha-D-glucopyranoside in crystalline form in 82% yield. Hydrogenolysis of the benzyl groups gave the title disaccharide, in crystalline form in 90% yield, which was characterized by a crystalline peracetylated alpha-D derivative.
D001593:Benzyl Compounds; D003460:Crystallization; D004187:Disaccharides / Q000138:chemical synthesis*; D005643:Fucose; D005947:Glucose; D006595:Hexosamines; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D009904:Optical Rotation
D001593:Benzyl Compounds; D004187:Disaccharides; D006595:Hexosamines; D005643:Fucose; D005947:Glucose
Synthèse du 2-acétamido-2-désoxy-4-O-alpha-L-fucopyranosyl-alpha-D-glucopyranose