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.
Documento: | Artículo |
Título: | Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained |
Autor: | Cerezo, A.S.; Deulofeu, V. |
Filiación: | Departamento de Quimica Orgánica, Facultad de Ciencias Exactas y Naturales, Perú, 222 Buenos Aires, Argentina |
Año: | 1966 |
Volumen: | 2 |
Número: | 1 |
Página de inicio: | 35 |
Página de fin: | 41 |
DOI: | http://dx.doi.org/10.1016/S0008-6215(00)81774-7 |
Título revista: | Carbohydrate Research |
Título revista abreviado: | Carbohydr. Res. |
ISSN: | 00086215 |
CODEN: | CRBRA |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v2_n1_p35_Cerezo |