M. Shaban, R. Jeanloz
Apr 1, 1972
Citations
0
Influential Citations
14
Citations
Journal
Carbohydrate Research
Abstract
Abstract The title compound, used in the synthesis of glycopeptides and as a reference substance in the structural elucidation of glycoproteins, was synthesized by condensation of 2,3,4,6-tetra- O -acetyl-α- d -mannopyranosyl bromide with 2-acetamido-4,6- O -benzylidene-α- d -glucopyranosyl azide, followed by removal of the benzylidene group to give the disaccharide azide 6 and acetylation. The resulting fully acetylated disaccharide azide 7 was also obtained by treatment of the known 2-acetamido-1,4,6-tri- O -acetyl-2-deoxy-3- O -(2,3,4,6-tetra- O -acetyl-α- d -mannopyranosyl)-α- d -glucopyranose with hydrogen chloride and then with silver azide. The azide 7 was reduced in presence of platinum oxide (Adams' catalyst), and the resulting amine was condensed with 1-benzyl N -benzyloxycarbonyl- l -aspartate in the presence of N , N ′-dicyclocarbodiimide. The removal of the protective group was accomplished by hydrogenolysis and O -deacetylation. In a second route, the disaccharide azide 6 was reduced and then condensed with 1-benzyl N -benzyloxycarbonyl- l -aspartate, and the resulting product hydrogenolyzed.