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
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-glucofur...
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| Autores principales: | , , |
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| Publicado: |
1987
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v170_n1_p71_Salinas http://hdl.handle.net/20.500.12110/paper_00086215_v170_n1_p71_Salinas |
| Aporte de: |
| Sumario: | 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. |
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