The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation

The reaction of ammonia with β-octa-O-acetylmaltose affords N,N′-diacetylmaltosylidenediamine (I), from which its acetate was prepared. A comparative study of the reaction in methanolic and in aqueous media was performed. The higher yield of I obtained in aqueous medium was qualitatively interpreted...

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Autores principales: Cadenas, Raúl Alberto, Deferrari, Jorge O.
Publicado: 1963
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v28_n10_p2613_Cadenas
http://hdl.handle.net/20.500.12110/paper_00223263_v28_n10_p2613_Cadenas
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
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spelling paper:paper_00223263_v28_n10_p2613_Cadenas2023-06-08T14:49:21Z The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation Cadenas, Raúl Alberto Deferrari, Jorge O. The reaction of ammonia with β-octa-O-acetylmaltose affords N,N′-diacetylmaltosylidenediamine (I), from which its acetate was prepared. A comparative study of the reaction in methanolic and in aqueous media was performed. The higher yield of I obtained in aqueous medium was qualitatively interpreted according to known kinetic studies about the reaction of ester ammonolysis, which is simultaneous and competitive with the reaction described. It is demonstrated that, in the reaction of penta-O-benzoyl-α-d-glucopyranose with methanolic ammonia, methyl benzoate is produced. Therefore, in that medium methoxide ions are formed, pointing out that, apart from the ammonolysis reaction and from the formation of “aldose–amides” by an ortho ester mechanism, a third competitive reaction takes place, by which acyl groups are split off through a transesterification mechanism. © 1963, American Chemical Society. All rights reserved. Fil:Cadenas, R.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Deferrari, J.O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1963 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v28_n10_p2613_Cadenas http://hdl.handle.net/20.500.12110/paper_00223263_v28_n10_p2613_Cadenas
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
description The reaction of ammonia with β-octa-O-acetylmaltose affords N,N′-diacetylmaltosylidenediamine (I), from which its acetate was prepared. A comparative study of the reaction in methanolic and in aqueous media was performed. The higher yield of I obtained in aqueous medium was qualitatively interpreted according to known kinetic studies about the reaction of ester ammonolysis, which is simultaneous and competitive with the reaction described. It is demonstrated that, in the reaction of penta-O-benzoyl-α-d-glucopyranose with methanolic ammonia, methyl benzoate is produced. Therefore, in that medium methoxide ions are formed, pointing out that, apart from the ammonolysis reaction and from the formation of “aldose–amides” by an ortho ester mechanism, a third competitive reaction takes place, by which acyl groups are split off through a transesterification mechanism. © 1963, American Chemical Society. All rights reserved.
author Cadenas, Raúl Alberto
Deferrari, Jorge O.
spellingShingle Cadenas, Raúl Alberto
Deferrari, Jorge O.
The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation
author_facet Cadenas, Raúl Alberto
Deferrari, Jorge O.
author_sort Cadenas, Raúl Alberto
title The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation
title_short The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation
title_full The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation
title_fullStr The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation
title_full_unstemmed The Reaction of Ammonia with Acylated Disaccharides. III. Acetyl Derivatives of Maltose and an Interpretation
title_sort reaction of ammonia with acylated disaccharides. iii. acetyl derivatives of maltose and an interpretation
publishDate 1963
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v28_n10_p2613_Cadenas
http://hdl.handle.net/20.500.12110/paper_00223263_v28_n10_p2613_Cadenas
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AT cadenasraulalberto reactionofammoniawithacylateddisaccharidesiiiacetylderivativesofmaltoseandaninterpretation
AT deferrarijorgeo reactionofammoniawithacylateddisaccharidesiiiacetylderivativesofmaltoseandaninterpretation
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