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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| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_00086215_v30_n2_p313_Deferrari |
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todo:paper_00086215_v30_n2_p313_Deferrari2023-10-03T14:06:52Z The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile Deferrari, J.O. Zuazo, B.N. Gelpi, M.E. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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. |
| format |
JOUR |
| author |
Deferrari, J.O. Zuazo, B.N. Gelpi, M.E. |
| spellingShingle |
Deferrari, J.O. Zuazo, B.N. Gelpi, M.E. The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile |
| author_facet |
Deferrari, J.O. Zuazo, B.N. Gelpi, M.E. |
| author_sort |
Deferrari, J.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 |
| url |
http://hdl.handle.net/20.500.12110/paper_00086215_v30_n2_p313_Deferrari |
| work_keys_str_mv |
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