Abstract:
The reaction of tetra-O-benzoyl-α-D-glucopyranosyl bromide with sodium azide afforded 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl azide (7). Hydrogenation of 7 produced 2,3,4,6-tetra-O-benzoyl-D-glucopyranosylamine (8), characterized as its hydrochloride (9). Ammonolysis of 8 produced 1,1-bis(benzamido)-1-deoxy-D-glucitol in very low yield (1.4%), traces of N-benzoyl-D-glucopyranosylamine, and a mixture (95%) of D-glucose and D-glucosylamine. This result strongly supports the concept that O → N acyl migrations are not favored in this reaction of a tetra-O-benzoyl-D-glucosylamine. © 1971.
Registro:
Documento: |
Artículo
|
Título: | Ammonolysis of 2,3,4,6-tetra-O-benzoyl-D-glucopyranosylamine |
Autor: | Sproviero, J.F.; Salinas, A.; Bertiche, E.S. |
Filiación: | Departamento de Quimica Orgánica, Facultad de Ciencias Exastas y Naturales, Universidad de Buenos Aires, Perú, 222 Buenos Aires, Argentina
|
Año: | 1971
|
Volumen: | 19
|
Número: | 1
|
Página de inicio: | 81
|
Página de fin: | 86
|
DOI: |
http://dx.doi.org/10.1016/S0008-6215(00)80314-6 |
Título revista: | Carbohydrate Research
|
Título revista abreviado: | Carbohydr. Res.
|
ISSN: | 00086215
|
CODEN: | CRBRA
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v19_n1_p81_Sproviero |
Referencias:
- Isaell, Frush, Orthoester Reactions of Sugar Acetates with Ammonia (1949) Journal of the American Chemical Society, 71, p. 1579
- Hockett, Deulofeu, Deferrari, (1950) J. Amer. Chem. Soc., 72, p. 1840
- Gros, Ondetti, Sproviero, Deulofeu, Deferrari, (1962) J. Org. Chem., 27, p. 924
- Gros, Deulofeu, (1964) J. Org. Chem., 29, p. 3647
- Lezerovich, Gros, Sproviero, Deulofeu, (1967) Carbohyd. Res., 4, p. 1
- Salinas, Sproviero, (1971) Carbohyd. Res., 16, p. 243
- Micheel, Klemer, Advan. Carbohyd. Chem. (1961) Advan. Carbohyd. Chem., 16, p. 85
- Bertho, Über Azidoderivate der Glucose (1930) Berichte der deutschen chemischen Gesellschaft (A and B Series), 63, p. 836. , with H. Nüssel
- Bertho, (1949) Ann., 562, p. 229. , with M. Beutler
- Ness, Fletcher, .Jr, Hudson, (1950) J. Amer. Chem. Soc., 72, p. 2200
- Cerezo, Sproviero, Deulofeu, Delpy, (1968) Carbohyd. Res., 7, p. 395
- Farkas, Szabó, Bognár, (1969) Acta Chim. Acad. Sci. Hung., 59, p. 419. , and references cited therein
- Deferrari, Gelpi, Cadenas, (1965) J. Org. Chem., 30, p. 2328
- Van de Kamp, Micheel, Über die Reaktionen desD-Glucosamins, VI. Acylwanderungen beiD-Glucosamin-Derivaten (1957) Chemische Berichte, 90, p. 2054
- Angyal, MacDonald, 124. Cyclitols. Part I. isoPropylidene derivatives of inositols and quercitols. The structure of pinitol and quebrachitol (1952) Journal of the Chemical Society (Resumed), p. 686
- Petronici, Safina, (1953) Conserve Deriv. Agrum., 2 (5), p. 3
- Petronici, Safina, (1953) Chem. Abstr., 47, p. 11297
Citas:
---------- APA ----------
Sproviero, J.F., Salinas, A. & Bertiche, E.S.
(1971)
. Ammonolysis of 2,3,4,6-tetra-O-benzoyl-D-glucopyranosylamine. Carbohydrate Research, 19(1), 81-86.
http://dx.doi.org/10.1016/S0008-6215(00)80314-6---------- CHICAGO ----------
Sproviero, J.F., Salinas, A., Bertiche, E.S.
"Ammonolysis of 2,3,4,6-tetra-O-benzoyl-D-glucopyranosylamine"
. Carbohydrate Research 19, no. 1
(1971) : 81-86.
http://dx.doi.org/10.1016/S0008-6215(00)80314-6---------- MLA ----------
Sproviero, J.F., Salinas, A., Bertiche, E.S.
"Ammonolysis of 2,3,4,6-tetra-O-benzoyl-D-glucopyranosylamine"
. Carbohydrate Research, vol. 19, no. 1, 1971, pp. 81-86.
http://dx.doi.org/10.1016/S0008-6215(00)80314-6---------- VANCOUVER ----------
Sproviero, J.F., Salinas, A., Bertiche, E.S. Ammonolysis of 2,3,4,6-tetra-O-benzoyl-D-glucopyranosylamine. Carbohydr. Res. 1971;19(1):81-86.
http://dx.doi.org/10.1016/S0008-6215(00)80314-6