Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine

The reaction of d-gluconamide with benzoyl chloride and pyridine gave a complex mixture from which ethyl or methyl 2,3,5,6-tetra-O-benzoyl-d-gluconate (5 and 6) crystallized after treatment with ethanol or methanol, respectively. These esters were formed by alcoholysis of 2,3,5,6-tetra-O-benzoyl-d-g...

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Autores principales: Deferrari, Jorge O., Muchnik de Lederkremer, Rosa María, Matsuhiro, Betty, Litter, Marta Irene
Publicado: 1970
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v14_n1_p103_Deferrari
http://hdl.handle.net/20.500.12110/paper_00086215_v14_n1_p103_Deferrari
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id paper:paper_00086215_v14_n1_p103_Deferrari
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spelling paper:paper_00086215_v14_n1_p103_Deferrari2023-06-08T14:32:16Z Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine Deferrari, Jorge O. Muchnik de Lederkremer, Rosa María Matsuhiro, Betty Litter, Marta Irene The reaction of d-gluconamide with benzoyl chloride and pyridine gave a complex mixture from which ethyl or methyl 2,3,5,6-tetra-O-benzoyl-d-gluconate (5 and 6) crystallized after treatment with ethanol or methanol, respectively. These esters were formed by alcoholysis of 2,3,5,6-tetra-O-benzoyl-d-glucono-1,4-lactone (4), which was isolated by column chromatography, together with penta-O-benzoyl-d-glucononitrile (7), penta-O-benzoyl-d-gluconamide (8), N-benzoyl-penta-O-benzoyl-d-gluconamide (9), and benzamide when an excess of benzoyl chloride was used. The isolation of 4 and benzamide was explained by the formation and hydrolysis of a benzoylated imino-lactone intermediate (3). © 1970. Fil:Deferrari, J.O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:de Lederkremer, R.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Matsuhiro, B. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Litter, M.I. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1970 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v14_n1_p103_Deferrari http://hdl.handle.net/20.500.12110/paper_00086215_v14_n1_p103_Deferrari
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 d-gluconamide with benzoyl chloride and pyridine gave a complex mixture from which ethyl or methyl 2,3,5,6-tetra-O-benzoyl-d-gluconate (5 and 6) crystallized after treatment with ethanol or methanol, respectively. These esters were formed by alcoholysis of 2,3,5,6-tetra-O-benzoyl-d-glucono-1,4-lactone (4), which was isolated by column chromatography, together with penta-O-benzoyl-d-glucononitrile (7), penta-O-benzoyl-d-gluconamide (8), N-benzoyl-penta-O-benzoyl-d-gluconamide (9), and benzamide when an excess of benzoyl chloride was used. The isolation of 4 and benzamide was explained by the formation and hydrolysis of a benzoylated imino-lactone intermediate (3). © 1970.
author Deferrari, Jorge O.
Muchnik de Lederkremer, Rosa María
Matsuhiro, Betty
Litter, Marta Irene
spellingShingle Deferrari, Jorge O.
Muchnik de Lederkremer, Rosa María
Matsuhiro, Betty
Litter, Marta Irene
Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine
author_facet Deferrari, Jorge O.
Muchnik de Lederkremer, Rosa María
Matsuhiro, Betty
Litter, Marta Irene
author_sort Deferrari, Jorge O.
title Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine
title_short Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine
title_full Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine
title_fullStr Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine
title_full_unstemmed Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine
title_sort anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine
publishDate 1970
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v14_n1_p103_Deferrari
http://hdl.handle.net/20.500.12110/paper_00086215_v14_n1_p103_Deferrari
work_keys_str_mv AT deferrarijorgeo anomalousreactionofdgluconamidewithbenzoylchlorideinanhydrouspyridine
AT muchnikdelederkremerrosamaria anomalousreactionofdgluconamidewithbenzoylchlorideinanhydrouspyridine
AT matsuhirobetty anomalousreactionofdgluconamidewithbenzoylchlorideinanhydrouspyridine
AT littermartairene anomalousreactionofdgluconamidewithbenzoylchlorideinanhydrouspyridine
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