Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained

The N-acetyl-d-glycofuranosylamines produced in the ammonolysis of acetylated d-xylopyranose and acetylated d-glucopyranose have been found to be the α-d anomers. These assignments were obtained by destroying the asymmetry of all of the carbon atoms but the anomeric one (by periodate oxidation) foll...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Cerezo, A.S., Deulofeu, V.
Formato: JOUR
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00086215_v2_n1_p35_Cerezo
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_00086215_v2_n1_p35_Cerezo
record_format dspace
spelling todo:paper_00086215_v2_n1_p35_Cerezo2023-10-03T14:06:47Z Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained Cerezo, A.S. Deulofeu, V. The N-acetyl-d-glycofuranosylamines produced in the ammonolysis of acetylated d-xylopyranose and acetylated d-glucopyranose have been found to be the α-d anomers. These assignments were obtained by destroying the asymmetry of all of the carbon atoms but the anomeric one (by periodate oxidation) followed by reduction of the resulting aldehydes with sodium borohydride, and comparing the optical rotations of the resulting products with those of known configuration. Application of Hudson's isorotation rules led to the same result. In the ammonolysis of tetra-O-acetyl-β-d-xylopyranose, the known N-acetyl-β-d-xylopyranosylamine is also produced. © 1966. Fil:Cerezo, A.S. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00086215_v2_n1_p35_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 The N-acetyl-d-glycofuranosylamines produced in the ammonolysis of acetylated d-xylopyranose and acetylated d-glucopyranose have been found to be the α-d anomers. These assignments were obtained by destroying the asymmetry of all of the carbon atoms but the anomeric one (by periodate oxidation) followed by reduction of the resulting aldehydes with sodium borohydride, and comparing the optical rotations of the resulting products with those of known configuration. Application of Hudson's isorotation rules led to the same result. In the ammonolysis of tetra-O-acetyl-β-d-xylopyranose, the known N-acetyl-β-d-xylopyranosylamine is also produced. © 1966.
format JOUR
author Cerezo, A.S.
Deulofeu, V.
spellingShingle Cerezo, A.S.
Deulofeu, V.
Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained
author_facet Cerezo, A.S.
Deulofeu, V.
author_sort Cerezo, A.S.
title Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained
title_short Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained
title_full Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained
title_fullStr Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained
title_full_unstemmed Reaction of ammonia with some acetylated and benzoylated monosaccharides. Part X. Assignment of the α-d configuration to the N-acetyl-d-glycofuranosylamines obtained
title_sort reaction of ammonia with some acetylated and benzoylated monosaccharides. part x. assignment of the α-d configuration to the n-acetyl-d-glycofuranosylamines obtained
url http://hdl.handle.net/20.500.12110/paper_00086215_v2_n1_p35_Cerezo
work_keys_str_mv AT cerezoas reactionofammoniawithsomeacetylatedandbenzoylatedmonosaccharidespartxassignmentoftheadconfigurationtothenacetyldglycofuranosylaminesobtained
AT deulofeuv reactionofammoniawithsomeacetylatedandbenzoylatedmonosaccharidespartxassignmentoftheadconfigurationtothenacetyldglycofuranosylaminesobtained
_version_ 1807315990398107648

Ejemplares similares