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Abstract:

The reaction of penta-O-benzoyl-α-d-glucopyranose with chloroform-1,4-dioxane-liquid ammonia gave 1,1-bis(benzamido)-6-O-benzoyl-1-deoxy-d-glucitol (29.0%), three partially benzoylated derivatives of N-benzoyl-α-d-glucofuranosylamine (23.6%), a small proportion of N-benzoyl-di-O-benzoyl-β-d-glucofuranosylamine (0.2%), and four partially benzoylated derivatives of α-d-glucopyranose (9.9%). The structures of the hitherto-unknown products, and their anomeric configurations, were established by chemical and spectroscopic methods. The conformations in solution of both anomers of N-benzoyl-d-glucofuranosylamine, their partially benzoylated derivatives isolated from the ammonolysis reaction, and the per-O-acetyl derivatives of the various compounds were analyzed by 1H-n.m.r. spectroscopy. © 1987.

Registro:

Documento: Artículo
Título:Ammonolysis of penta-O-benzoyl-α-d-glucopyranose in an aprotic medium. Characterization of the products isolated, and conformational analysis of eleven N-benzoyl-d-glucofuranosylamine derivatives
Autor:Salinas, A.E.; Sproviero, J.F.; Deulofeu, V.
Filiación:Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon II, Ciudad Universitaria, 1428 Buenos Aires, Argentina
Año:1987
Volumen:170
Número:1
Página de inicio:71
Página de fin:99
DOI: http://dx.doi.org/10.1016/0008-6215(87)85006-1
Título revista:Carbohydrate Research
Título revista abreviado:Carbohydr. Res.
ISSN:00086215
CODEN:CRBRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v170_n1_p71_Salinas

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Citas:

---------- APA ----------
Salinas, A.E., Sproviero, J.F. & Deulofeu, V. (1987) . Ammonolysis of penta-O-benzoyl-α-d-glucopyranose in an aprotic medium. Characterization of the products isolated, and conformational analysis of eleven N-benzoyl-d-glucofuranosylamine derivatives. Carbohydrate Research, 170(1), 71-99.
http://dx.doi.org/10.1016/0008-6215(87)85006-1
---------- CHICAGO ----------
Salinas, A.E., Sproviero, J.F., Deulofeu, V. "Ammonolysis of penta-O-benzoyl-α-d-glucopyranose in an aprotic medium. Characterization of the products isolated, and conformational analysis of eleven N-benzoyl-d-glucofuranosylamine derivatives" . Carbohydrate Research 170, no. 1 (1987) : 71-99.
http://dx.doi.org/10.1016/0008-6215(87)85006-1
---------- MLA ----------
Salinas, A.E., Sproviero, J.F., Deulofeu, V. "Ammonolysis of penta-O-benzoyl-α-d-glucopyranose in an aprotic medium. Characterization of the products isolated, and conformational analysis of eleven N-benzoyl-d-glucofuranosylamine derivatives" . Carbohydrate Research, vol. 170, no. 1, 1987, pp. 71-99.
http://dx.doi.org/10.1016/0008-6215(87)85006-1
---------- VANCOUVER ----------
Salinas, A.E., Sproviero, J.F., Deulofeu, V. Ammonolysis of penta-O-benzoyl-α-d-glucopyranose in an aprotic medium. Characterization of the products isolated, and conformational analysis of eleven N-benzoyl-d-glucofuranosylamine derivatives. Carbohydr. Res. 1987;170(1):71-99.
http://dx.doi.org/10.1016/0008-6215(87)85006-1