Synthesis of benzyl 2-acetamido-2-deoxy-3-O-β-d-fucopyranosyl-α-d-galactopyranoside and benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-2-deoxy-3-O-β-d-fucopyranosyl-α-d-galactopyranoside

✍ Scribed by Conrad F. Piskorz; Saeed A. Abbas; Khushi L. Matta

• Publisher: Elsevier Science
• Year: 1984
• Tongue: English
• Weight: 428 KB
• Volume: 131
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(84)85247-7

✦ Synopsis

Condensation of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-a-D-galactopyranoside with 2,3,4-tri-o-acetyl-a-D-fucopyranosyl bromide in 1: 1 nitromethane-benzene, in the presence of powdered mercuric cyanide, afforded benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-0-(2,3,4-tri-O-acetyl-P-D-fucopyranosyl)-cu-D-galactopyranoside (3). Cleavage of the benzylidene group of 3 with hot, 60% aqueous acetic acid afforded diol 4, which, on deacetylation, furnished the disaccharide 5. Condensation of dio14 with 2-methyl-(3,4,6-tri-0-acetyl-1,2-dideoxy-a-D-glucopyrano)-[2,1-d]-2oxazoline in 1,2-dichloroethane afforded the trisaccharide derivative (7). Deacetylation of 7 with Amberlyst A-26 (OH-) anionexchange resin in methanol gave the title trisaccharide (8). The structures of 5 and 8 were confirmed by 13C-n.m.r. spectroscopy. *Synthetic Studies in Carbohydrates, Part XXXVIII. For Part XXXVII, see ref. 1.