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...
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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v26_n2_p357_Sproviero |
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todo:paper_00086215_v26_n2_p357_Sproviero2023-10-03T14:06:42Z Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine Sproviero, J.F. 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. Fil:Sproviero, J.F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v26_n2_p357_Sproviero |
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Universidad de Buenos Aires |
| institution_str |
I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| description |
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. |
| format |
JOUR |
| author |
Sproviero, J.F. |
| spellingShingle |
Sproviero, J.F. Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine |
| author_facet |
Sproviero, J.F. |
| author_sort |
Sproviero, J.F. |
| title |
Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine |
| title_short |
Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine |
| title_full |
Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine |
| title_fullStr |
Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine |
| title_full_unstemmed |
Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine |
| title_sort |
stereospecificity of the o→n acyl migration in 2,3,4,6-tetra-o-benzoyl-β-d-mannopyranosylamine |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v26_n2_p357_Sproviero |
| work_keys_str_mv |
AT sprovierojf stereospecificityoftheonacylmigrationin2346tetraobenzoylbdmannopyranosylamine |
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1807319424893452288 |