Harald Paulsen
Feb 28, 1985
Citations
0
Influential Citations
57
Citations
Journal
Carbohydrate Research
Abstract
Abstract The azidonitration of 3,4,6-tri- O -acetyl-1,5-anhydro-2-deoxy- d - arabino -hex-1-enitol at low temperature afforded preponderantly the azidonitrate having the d - manno configuration. After reaction with sodium acetate, 1,3,4,6-tetra- O -acetyl-2-azido-2-deoxy-α- d -mannopyranose was directly isolated and deblocking gave 2-azido-2-deoxy- d -mannopyranose. 3,4,6-Tri- O -acetyl-2-azido-2-deoxy-α- d -mannopyranosyl bromide and 2-azido-3,4,6-tri- O -benzyl-α- d -mannopyranosyl bromide were prepared and are suitable for selective α- and β-glycoside synthesis. In the presence of platinum-oxygen, the catalytic oxidation of benzyl 2-azido-2-deoxy-α- d -mannopyranoside gave in high yields (benzyl 2-azido-2-deoxy-α- d -mannopyranosid)uronic acid from which 2-amino-2-deoxy- d -mannopyranuronic acid was obtained. By catalytic oxidation, selectively blocked derivatives of 2-amino-2-deoxy- d -mannopyranose were converted into the corresponding uronic acid derivatives.