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...

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Autores principales: Cerezo, Alberto Saúl, Deulofeu, Venancio
Publicado: 1966
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v2_n1_p35_Cerezo
http://hdl.handle.net/20.500.12110/paper_00086215_v2_n1_p35_Cerezo
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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_v2_n1_p35_Cerezo2023-06-08T14:32:34Z 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, Alberto Saúl Deulofeu, Venancio 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. 1966 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v2_n1_p35_Cerezo 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.
author Cerezo, Alberto Saúl
Deulofeu, Venancio
spellingShingle Cerezo, Alberto Saúl
Deulofeu, Venancio
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, Alberto Saúl
Deulofeu, Venancio
author_sort Cerezo, Alberto Saúl
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
publishDate 1966
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v2_n1_p35_Cerezo
http://hdl.handle.net/20.500.12110/paper_00086215_v2_n1_p35_Cerezo
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AT deulofeuvenancio reactionofammoniawithsomeacetylatedandbenzoylatedmonosaccharidespartxassignmentoftheadconfigurationtothenacetyldglycofuranosylaminesobtained
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