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, J.O., de Lederkremer, R.M., Matsuhiro, B., Litter, M.I.
Formato: JOUR
Acceso en línea: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
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spelling todo:paper_00086215_v14_n1_p103_Deferrari2023-10-03T14:06:22Z Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine Deferrari, J.O. de Lederkremer, R.M. Matsuhiro, B. Litter, M.I. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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.
format JOUR
author Deferrari, J.O.
de Lederkremer, R.M.
Matsuhiro, B.
Litter, M.I.
spellingShingle Deferrari, J.O.
de Lederkremer, R.M.
Matsuhiro, B.
Litter, M.I.
Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine
author_facet Deferrari, J.O.
de Lederkremer, R.M.
Matsuhiro, B.
Litter, M.I.
author_sort Deferrari, J.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
url http://hdl.handle.net/20.500.12110/paper_00086215_v14_n1_p103_Deferrari
work_keys_str_mv AT deferrarijo anomalousreactionofdgluconamidewithbenzoylchlorideinanhydrouspyridine
AT delederkremerrm anomalousreactionofdgluconamidewithbenzoylchlorideinanhydrouspyridine
AT matsuhirob anomalousreactionofdgluconamidewithbenzoylchlorideinanhydrouspyridine
AT littermi anomalousreactionofdgluconamidewithbenzoylchlorideinanhydrouspyridine
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