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.
Documento: | Artículo |
Título: | The reaction of ammonia with acylated disaccharides. XI. The wohl reaction with octa-O-acytylmelibiononitrile |
Autor: | Deferrari, J.O.; Zuazo, B.N.; Gelpi, M.E. |
Filiación: | Departamento de Quimica Organica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón II, Ciudad Universitaria, Buenos Aires Argentina |
Año: | 1973 |
Volumen: | 30 |
Número: | 2 |
Página de inicio: | 313 |
Página de fin: | 318 |
DOI: | http://dx.doi.org/10.1016/S0008-6215(00)81817-0 |
Título revista: | Carbohydrate Research |
Título revista abreviado: | Carbohydr. Res. |
ISSN: | 00086215 |
CODEN: | CRBRA |
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v30_n2_p313_Deferrari |