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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| Publicado: |
1963
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| 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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| Sumario: | 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. |
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