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: Salinas, Amelia Esther, Sproviero, Jorge Félix, Deulofeu, Venancio
Publicado: 1987
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
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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_00086215_v170_n1_p71_Salinas2023-06-08T14:32:21Z 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 Salinas, Amelia Esther Sproviero, Jorge Félix Deulofeu, Venancio 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. Fil:Salinas, A.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Sproviero, J.F. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Deulofeu, V. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1987 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
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 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.
author Salinas, Amelia Esther
Sproviero, Jorge Félix
Deulofeu, Venancio
spellingShingle Salinas, Amelia Esther
Sproviero, Jorge Félix
Deulofeu, Venancio
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
author_facet Salinas, Amelia Esther
Sproviero, Jorge Félix
Deulofeu, Venancio
author_sort Salinas, Amelia Esther
title 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
title_short 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_sort 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
publishDate 1987
url 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
work_keys_str_mv AT salinasameliaesther ammonolysisofpentaobenzoyladglucopyranoseinanaproticmediumcharacterizationoftheproductsisolatedandconformationalanalysisofelevennbenzoyldglucofuranosylaminederivatives
AT sprovierojorgefelix ammonolysisofpentaobenzoyladglucopyranoseinanaproticmediumcharacterizationoftheproductsisolatedandconformationalanalysisofelevennbenzoyldglucofuranosylaminederivatives
AT deulofeuvenancio ammonolysisofpentaobenzoyladglucopyranoseinanaproticmediumcharacterizationoftheproductsisolatedandconformationalanalysisofelevennbenzoyldglucofuranosylaminederivatives
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