Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained
The N-acetyl-d-glycofuranosylamines produced in the ammonolysis of acetylated d-xylopyranose and acetylated d-glucopyranose have been found to be the α-d anomers. These assignments were obtained by destroying the asymmetry of all of the carbon atoms but the anomeric one (by periodate oxidation) foll...
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| Autores principales: | , |
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| Publicado: |
1966
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v2_n1_p35_Cerezo http://hdl.handle.net/20.500.12110/paper_00086215_v2_n1_p35_Cerezo |
| Aporte de: |
| Sumario: | The N-acetyl-d-glycofuranosylamines produced in the ammonolysis of acetylated d-xylopyranose and acetylated d-glucopyranose have been found to be the α-d anomers. These assignments were obtained by destroying the asymmetry of all of the carbon atoms but the anomeric one (by periodate oxidation) followed by reduction of the resulting aldehydes with sodium borohydride, and comparing the optical rotations of the resulting products with those of known configuration. Application of Hudson's isorotation rules led to the same result. In the ammonolysis of tetra-O-acetyl-β-d-xylopyranose, the known N-acetyl-β-d-xylopyranosylamine is also produced. © 1966. |
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