S. S. Rana, J. Barlow, K. Matta
Mar 16, 1982
Citations
0
Influential Citations
8
Citations
Journal
Carbohydrate Research
Abstract
Abstract The reaction of phenyl 2-acetamido-3,6-di- O -acetyl-2-deoxy-β- d -glucopyranoside with 2,3,4-tri- O -benzyl-α- l -fucopyranosyl bromide (catalyzed by bromide ion) proceeded readily, to give the protected, 4- O -substituted α- l -fucopyranosyl derivative which, on O -deacetylation, followed by hydrogenolysis, gave phenyl 2-acetamido-2-deoxy-4- O -α- l -fucopyranosyl-β- d -glucopyranoside. The reaction of 2-acetamido-1,3,4-tri- O -acetyl-2-deoxy-β- d -glucopyranose with the same glycosyl bromide under similar conditions gave the protected disaccharide derivative which, on hydrogenolysis, furnished 2-acetamido-1,3,4-tri- O -acetyl-2-deoxy-6- O -α- l -fucopyranosyl-β- d -glucopyranose ( 9 ). Treatment of compound 9 with acetyl chloride provided the corresponding glycosyl halide which, on reaction with sodium p -nitrophenoxide in N , N -dimethylformamide, gave compound 12 . O -Deacetylation of 12 gave p -nitrophenyl 2-acetamido-2-deoxy-6- O -α- l -fucopyranosyl-β- d -glucopyranoside. The synthesis of p -nitrophenyl 2-acetamido-2-deoxy-6- O -β- l -fucopyranosyl-β- d -glucopyranoside is also described. The structures of the final disaccharides were established by 1 H- and 13 C-n.m.r. spectroscopy.