Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine
By heating tetra-O-benzoyl-α-D-mannopyranosyl bromide with sodium azide, 2,3,4,6-tetra-O-benzoyl-β-d-mannopyranosyl azide (3) was obtained. Catalytic hydrogenation of 3 produced 2,3,4,6-tetra-O-benzoyl-β-d-mannopyranosylamine (4). Ammonolysis of 4 afforded N-benzoyl-β-d-mannopyranosylamine (7) in go...
Guardado en:
| Autor principal: | |
|---|---|
| Formato: | JOUR |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v26_n2_p357_Sproviero |
| Aporte de: |
| Sumario: | By heating tetra-O-benzoyl-α-D-mannopyranosyl bromide with sodium azide, 2,3,4,6-tetra-O-benzoyl-β-d-mannopyranosyl azide (3) was obtained. Catalytic hydrogenation of 3 produced 2,3,4,6-tetra-O-benzoyl-β-d-mannopyranosylamine (4). Ammonolysis of 4 afforded N-benzoyl-β-d-mannopyranosylamine (7) in good yield (60%) and a mixture of d-mannose and d-mannopyranosylamine (34%). No other compound was characterized. This result shows that, in O-acylated glycosylamines, O→N acyl migration is stereospecific and takes place when there is a cis relation between the O-acyl group at O-2 and the amino group at C-1. © 1973. |
|---|