Artículo
Sproviero, J.F. "Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine" (1973) Carbohydrate Research. 26(2):357-363
Consulte la política de Acceso Abierto del editor
Abstract:
By heating tetra-O-benzoyl-α-D-mannopyranosyl bromide with sodium azide, 2,3,4,6-tetra-O-benzoyl-β-d-mannopyranosyl azide (3) was obtained. Catalytic hydrogenation of 3 produced 2,3,4,6-tetra-O-benzoyl-β-d-mannopyranosylamine (4). Ammonolysis of 4 afforded N-benzoyl-β-d-mannopyranosylamine (7) in good yield (60%) and a mixture of d-mannose and d-mannopyranosylamine (34%). No other compound was characterized. This result shows that, in O-acylated glycosylamines, O→N acyl migration is stereospecific and takes place when there is a cis relation between the O-acyl group at O-2 and the amino group at C-1. © 1973.
Registro:
| Documento: | Artículo |
| Título: | Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine |
| Autor: | Sproviero, J.F. |
| Filiación: | Departamento de Quimica Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, Buenos Aires Argentina |
| Año: | 1973 |
| Volumen: | 26 |
| Número: | 2 |
| Página de inicio: | 357 |
| Página de fin: | 363 |
| DOI: | http://dx.doi.org/10.1016/S0008-6215(00)84523-1 |
| Título revista: | Carbohydrate Research |
| Título revista abreviado: | Carbohydr. Res. |
| ISSN: | 00086215 |
| CODEN: | CRBRA |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v26_n2_p357_Sproviero |
Referencias:
- Sproviero, Salinas, Bertiche, (1971) Carbohyd. Res., 19, p. 81
- Anderson, Lardy, (1950) J. Amer. Chem. Soc., 72, p. 3141
- McCasland, (1951) J. Amer. Chem. Soc., 73, p. 2295
- Fodor, Kiss, (1950) J. Amer. Chem. Soc., 72, p. 3495
- White, 285. Studies in the amino-sugars. Part I. A case of acyl migration (1938) Journal of the Chemical Society (Resumed), p. 1498
- Fodor, Otvös, Die Raumstruktur der Aminodesoxyzucker, II. Mitteil.: Die Konstellation des D-Glucosamins (1956) Chemische Berichte, 89, p. 701
- Micheel, van de Kamp, Petersen, Über die Reaktionen desD-Glucosamins, IV. Die Acetohalogenverbindungen desD-Glucosamins (1957) Chemische Berichte, 90, p. 521
- Micheel, van de Kamp, Wulff, Über die Struktur der Acetobromverbindungen desD-Glucosamins (1955) Chemische Berichte, 88, p. 2011
- van de Kamp, Micheel, Über die Reaktionen desD-Glucosamins, VI. Acylwanderungen beiD-Glucosamin-Derivaten (1957) Chemische Berichte, 90, p. 2054
- Inch, Fletcher, Jr., (1966) J. Org. Chem., 31, p. 1821
- Horton, Mast, Philips, (1967) J. Org. Chem., 32, p. 1471
- Ness, Fletcher, Jr., Hudson, (1950) J. Amer. Chem. Soc., 72, p. 521
- Isbell, Frush, (1958) J. Org. Chem., 23, p. 1309
- Deferrari, Deulofeu, (1952) J. Org. Chem., 17, p. 1093
- Zanlungo, Deferrari, Cadenas, Acyl migrations in acylated monosaccharides. Formation of N-acetyl-β-D-galactofuranosylamine (1969) Carbohydrate Research, 10, p. 403
- Cerezo, (1971) Chem. Ind., p. 96. , London
- Fodor, Letourneau, Mandava, Etude spectroscopique de l'intermédiaire des migrations d'acyleO → Ndans le β-éthyl triacétyl-3,4,6 désoxy-2 amino-2D-glucoside (1970) Canadian Journal of Chemistry, 48, p. 1465
- Isbell, Frush, (1949) J. Amer. Chem. Soc., 71, p. 1579
- Gros, Ondetti, Sproviero, Deulofeu, Deferrari, (1962) J. Org. Chem., 27, p. 924
- Petronici, Safina, (1953) Conserve Deriv. Agrum., 5 (2), p. 3. , Chem. Abstr. 47 1953 11297
- Mastronardi, Flematti, Deferrari, Gros, (1966) Carbohyd. Res., 3, p. 177
Citas:
---------- APA ----------
(1973) . Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine. Carbohydrate Research, 26(2), 357-363.http://dx.doi.org/10.1016/S0008-6215(00)84523-1
---------- CHICAGO ----------
Sproviero, J.F. "Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine" . Carbohydrate Research 26, no. 2 (1973) : 357-363.http://dx.doi.org/10.1016/S0008-6215(00)84523-1
---------- MLA ----------
Sproviero, J.F. "Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine" . Carbohydrate Research, vol. 26, no. 2, 1973, pp. 357-363.http://dx.doi.org/10.1016/S0008-6215(00)84523-1
---------- VANCOUVER ----------
Sproviero, J.F. Stereospecificity of the O→N acyl migration in 2,3,4,6-tetra-O-benzoyl-β-D-mannopyranosylamine. Carbohydr. Res. 1973;26(2):357-363.http://dx.doi.org/10.1016/S0008-6215(00)84523-1
