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Abstract:

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.

Registro:

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

Citas:

---------- APA ----------
Cerezo, A.S. & Deulofeu, V. (1966) . Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained. Carbohydrate Research, 2(1), 35-41.
http://dx.doi.org/10.1016/S0008-6215(00)81774-7
---------- CHICAGO ----------
Cerezo, A.S., Deulofeu, V. "Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained" . Carbohydrate Research 2, no. 1 (1966) : 35-41.
http://dx.doi.org/10.1016/S0008-6215(00)81774-7
---------- MLA ----------
Cerezo, A.S., Deulofeu, V. "Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained" . Carbohydrate Research, vol. 2, no. 1, 1966, pp. 35-41.
http://dx.doi.org/10.1016/S0008-6215(00)81774-7
---------- VANCOUVER ----------
Cerezo, A.S., Deulofeu, V. Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained. Carbohydr. Res. 1966;2(1):35-41.
http://dx.doi.org/10.1016/S0008-6215(00)81774-7