The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile

Octa-O-acetylmelibiononitrile (1) was prepared from melibiose oxime. The reaction of aqueous ammonia with 1 gave 1,1-bis(acetamido)-1-deoxy-5-O-α-D-galactopyranosyl-D-arabinitol (2), N-acetyl-5-O-α-D-galactopyranosyl-α-D-arabinofuranosylamine (3), and the anomeric pair of 5-O-α-D-galactopyranosyl-D-...

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Autores principales: Deferrari, Jorge O., Zuazo, Beatriz Noemí, Gelpi, María Elena
Publicado: 1973
Acceso en línea:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v30_n2_p313_Deferrari
http://hdl.handle.net/20.500.12110/paper_00086215_v30_n2_p313_Deferrari
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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_v30_n2_p313_Deferrari2023-06-08T14:32:36Z The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile Deferrari, Jorge O. Zuazo, Beatriz Noemí Gelpi, María Elena Octa-O-acetylmelibiononitrile (1) was prepared from melibiose oxime. The reaction of aqueous ammonia with 1 gave 1,1-bis(acetamido)-1-deoxy-5-O-α-D-galactopyranosyl-D-arabinitol (2), N-acetyl-5-O-α-D-galactopyranosyl-α-D-arabinofuranosylamine (3), and the anomeric pair of 5-O-α-D-galactopyranosyl-D-arabinofuranoses (4 and 5). The hepta-O-acetyl derivative of 2 was prepared, and the acyclic structure of the nitrogen-containing moiety was established by oxidation with periodate. The α anomeric configuration of 3 was demonstrated by periodate oxidation and subsequent reduction with sodium borohydride and hydrolysis. © 1973. Fil:Deferrari, J.O. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Zuazo, B.N. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gelpi, M.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. 1973 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v30_n2_p313_Deferrari http://hdl.handle.net/20.500.12110/paper_00086215_v30_n2_p313_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 Octa-O-acetylmelibiononitrile (1) was prepared from melibiose oxime. The reaction of aqueous ammonia with 1 gave 1,1-bis(acetamido)-1-deoxy-5-O-α-D-galactopyranosyl-D-arabinitol (2), N-acetyl-5-O-α-D-galactopyranosyl-α-D-arabinofuranosylamine (3), and the anomeric pair of 5-O-α-D-galactopyranosyl-D-arabinofuranoses (4 and 5). The hepta-O-acetyl derivative of 2 was prepared, and the acyclic structure of the nitrogen-containing moiety was established by oxidation with periodate. The α anomeric configuration of 3 was demonstrated by periodate oxidation and subsequent reduction with sodium borohydride and hydrolysis. © 1973.
author Deferrari, Jorge O.
Zuazo, Beatriz Noemí
Gelpi, María Elena
spellingShingle Deferrari, Jorge O.
Zuazo, Beatriz Noemí
Gelpi, María Elena
The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile
author_facet Deferrari, Jorge O.
Zuazo, Beatriz Noemí
Gelpi, María Elena
author_sort Deferrari, Jorge O.
title The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile
title_short The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile
title_full The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile
title_fullStr The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile
title_full_unstemmed The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile
title_sort reaction of ammonia with acylated disaccharides. xi. the wohl reaction with octa-o-acytylmelibiononitrile
publishDate 1973
url https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v30_n2_p313_Deferrari
http://hdl.handle.net/20.500.12110/paper_00086215_v30_n2_p313_Deferrari
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