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Abstract:

NewN-acyl-D-glucosylamines (2,3) and 1,1-bis(acylamido)-1-deoxy-D-glucitols (1) have been isolated by applying chromatographic and ionophoretic techniques to the separation of the products from the ammonolysis of penta-O-acetyl-, penta-O-propionyl-, and penta-O-benzoyl-D-glucopyranose. It has been found that, in all cases, acyclic (1) and cyclic (2, 3) products are formed simultaneously. The molar ratio of the cyclic products formed (2+3) to the acyclic ones (1) is higher if the acyl group is aliphatic. The yield ofN-benzoyl-β-D-mannopyranosylamine obtained in the ammonolysis of penta-O-benzoyl-D-mannopyranose is higher than that ofN-benzoyl-β-D-glucopyranosylamine from penta-O-benzoyl-D-glucopyranose, showing the influence of inversion of configuration at C-2. This influence is less pronounced for other acylated monosaccharides that belong to themanno series. © 1968 Elsevier Publishing Company, Amsterdam.

Registro:

Documento: Artículo
Título:Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses
Autor:Cerezo, A.S.; Sproviero, J.F.; Deulofeu, V.; Delpy, S.
Filiación:Departamento de Quimica Orga ́nica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Peru, ́222 Buenos Aires, Argentina
Año:1968
Volumen:7
Número:4
Página de inicio:395
Página de fin:404
DOI: http://dx.doi.org/10.1016/S0008-6215(00)82957-2
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v7_n4_p395_Cerezo

Citas:

---------- APA ----------
Cerezo, A.S., Sproviero, J.F., Deulofeu, V. & Delpy, S. (1968) . Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses. Carbohydrate Research, 7(4), 395-404.
http://dx.doi.org/10.1016/S0008-6215(00)82957-2
---------- CHICAGO ----------
Cerezo, A.S., Sproviero, J.F., Deulofeu, V., Delpy, S. "Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses" . Carbohydrate Research 7, no. 4 (1968) : 395-404.
http://dx.doi.org/10.1016/S0008-6215(00)82957-2
---------- MLA ----------
Cerezo, A.S., Sproviero, J.F., Deulofeu, V., Delpy, S. "Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses" . Carbohydrate Research, vol. 7, no. 4, 1968, pp. 395-404.
http://dx.doi.org/10.1016/S0008-6215(00)82957-2
---------- VANCOUVER ----------
Cerezo, A.S., Sproviero, J.F., Deulofeu, V., Delpy, S. Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses. Carbohydr. Res. 1968;7(4):395-404.
http://dx.doi.org/10.1016/S0008-6215(00)82957-2