Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses

NewN-acyl-D-glucosylamines (2,3) and 1,1-bis(acylamido)-1-deoxy-D-glucitols (1) have been isolated by applying chromatographic and ionophoretic techniques to the separation of the products from the ammonolysis of penta-O-acetyl-, penta-O-propionyl-, and penta-O-benzoyl-D-glucopyranose. It has been f...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Cerezo, A.S., Sproviero, J.F., Deulofeu, V., Delpy, S.
Formato: JOUR
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00086215_v7_n4_p395_Cerezo
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_00086215_v7_n4_p395_Cerezo
record_format dspace
spelling todo:paper_00086215_v7_n4_p395_Cerezo2023-10-03T14:07:40Z Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses Cerezo, A.S. Sproviero, J.F. Deulofeu, V. Delpy, S. NewN-acyl-D-glucosylamines (2,3) and 1,1-bis(acylamido)-1-deoxy-D-glucitols (1) have been isolated by applying chromatographic and ionophoretic techniques to the separation of the products from the ammonolysis of penta-O-acetyl-, penta-O-propionyl-, and penta-O-benzoyl-D-glucopyranose. It has been found that, in all cases, acyclic (1) and cyclic (2, 3) products are formed simultaneously. The molar ratio of the cyclic products formed (2+3) to the acyclic ones (1) is higher if the acyl group is aliphatic. The yield ofN-benzoyl-β-D-mannopyranosylamine obtained in the ammonolysis of penta-O-benzoyl-D-mannopyranose is higher than that ofN-benzoyl-β-D-glucopyranosylamine from penta-O-benzoyl-D-glucopyranose, showing the influence of inversion of configuration at C-2. This influence is less pronounced for other acylated monosaccharides that belong to themanno series. © 1968 Elsevier Publishing Company, Amsterdam. Fil:Cerezo, A.S. 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. Fil:Delpy, S. 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_v7_n4_p395_Cerezo
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
description NewN-acyl-D-glucosylamines (2,3) and 1,1-bis(acylamido)-1-deoxy-D-glucitols (1) have been isolated by applying chromatographic and ionophoretic techniques to the separation of the products from the ammonolysis of penta-O-acetyl-, penta-O-propionyl-, and penta-O-benzoyl-D-glucopyranose. It has been found that, in all cases, acyclic (1) and cyclic (2, 3) products are formed simultaneously. The molar ratio of the cyclic products formed (2+3) to the acyclic ones (1) is higher if the acyl group is aliphatic. The yield ofN-benzoyl-β-D-mannopyranosylamine obtained in the ammonolysis of penta-O-benzoyl-D-mannopyranose is higher than that ofN-benzoyl-β-D-glucopyranosylamine from penta-O-benzoyl-D-glucopyranose, showing the influence of inversion of configuration at C-2. This influence is less pronounced for other acylated monosaccharides that belong to themanno series. © 1968 Elsevier Publishing Company, Amsterdam.
format JOUR
author Cerezo, A.S.
Sproviero, J.F.
Deulofeu, V.
Delpy, S.
spellingShingle Cerezo, A.S.
Sproviero, J.F.
Deulofeu, V.
Delpy, S.
Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses
author_facet Cerezo, A.S.
Sproviero, J.F.
Deulofeu, V.
Delpy, S.
author_sort Cerezo, A.S.
title Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses
title_short Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses
title_full Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses
title_fullStr Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses
title_full_unstemmed Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part XII.N-acyl-D-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-D-glucitols isolated from the ammonolysis of different penta-O-acyl-D-glucoses
title_sort reaction of ammonia with some acetylated and benzoylated monosaccharides. part xii.n-acyl-d-glucosylamines and 1, 1-bis(acylamido)-1-deoxy-d-glucitols isolated from the ammonolysis of different penta-o-acyl-d-glucoses
url http://hdl.handle.net/20.500.12110/paper_00086215_v7_n4_p395_Cerezo
work_keys_str_mv AT cerezoas reactionofammoniawithsomeacetylatedandbenzoylatedmonosaccharidespartxiinacyldglucosylaminesand11bisacylamido1deoxydglucitolsisolatedfromtheammonolysisofdifferentpentaoacyldglucoses
AT sprovierojf reactionofammoniawithsomeacetylatedandbenzoylatedmonosaccharidespartxiinacyldglucosylaminesand11bisacylamido1deoxydglucitolsisolatedfromtheammonolysisofdifferentpentaoacyldglucoses
AT deulofeuv reactionofammoniawithsomeacetylatedandbenzoylatedmonosaccharidespartxiinacyldglucosylaminesand11bisacylamido1deoxydglucitolsisolatedfromtheammonolysisofdifferentpentaoacyldglucoses
AT delpys reactionofammoniawithsomeacetylatedandbenzoylatedmonosaccharidespartxiinacyldglucosylaminesand11bisacylamido1deoxydglucitolsisolatedfromtheammonolysisofdifferentpentaoacyldglucoses
_version_ 1807315572760772608

Ejemplares similares