Artículo
Deferrari, J.O.; de Lederkremer, R.M.; Matsuhiro, B.; Litter, M.I. "Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine" (1970) Carbohydrate Research. 14(1):103-107
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Abstract:
The reaction of d-gluconamide with benzoyl chloride and pyridine gave a complex mixture from which ethyl or methyl 2,3,5,6-tetra-O-benzoyl-d-gluconate (5 and 6) crystallized after treatment with ethanol or methanol, respectively. These esters were formed by alcoholysis of 2,3,5,6-tetra-O-benzoyl-d-glucono-1,4-lactone (4), which was isolated by column chromatography, together with penta-O-benzoyl-d-glucononitrile (7), penta-O-benzoyl-d-gluconamide (8), N-benzoyl-penta-O-benzoyl-d-gluconamide (9), and benzamide when an excess of benzoyl chloride was used. The isolation of 4 and benzamide was explained by the formation and hydrolysis of a benzoylated imino-lactone intermediate (3). © 1970.
Registro:
| Documento: | Artículo |
| Título: | Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine |
| Autor: | Deferrari, J.O.; de Lederkremer, R.M.; Matsuhiro, B.; Litter, M.I. |
| Filiación: | Departamento de Quimica Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Perú, 222 Buenos Aires, Argentina |
| Año: | 1970 |
| Volumen: | 14 |
| Número: | 1 |
| Página de inicio: | 103 |
| Página de fin: | 107 |
| DOI: | http://dx.doi.org/10.1016/S0008-6215(00)80704-1 |
| Título revista: | Carbohydrate Research |
| Título revista abreviado: | Carbohydr. Res. |
| ISSN: | 00086215 |
| CODEN: | CRBRA |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v14_n1_p103_Deferrari |
Referencias:
- Jelinek, Upson, (1938) J. Amer. Chem. Soc., 60, p. 355
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- Wolfrom, Bennett, Synthesis of L-threo-Pentulose and 3,4,5-Tri-O-benzoyl-1-deoxy-L-threo-pentulose1 (1965) The Journal of Organic Chemistry, 30, p. 458
- Matsuhiro, (1963) Thesis Facultad de Ciencias Exactas y Naturales, , Universidad de Buenos Aires
- Deferrari, Matsuhiro, (1967) An. Asoc. Quim. Argent., 55, p. 187
- de Lederkremer, Cirelli, Deferrari, (1970) Carbohyd. Res., 13, p. 9
- Wolfrom, Bennet, Crum, (1958) J. Amer. Chem. Soc., 80, p. 944
- Weerman, L'action de l'hypochlorite de sodium sur les amides d'α-hydroxy-acides et de polyhydroxy-acides, ayant un groupe hydroxyle à la place α. Nouvelle méthode de dégradation des sucres (1918) Recueil des Travaux Chimiques des Pays-Bas et de la Belgique, 37, p. 16
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Citas:
---------- APA ----------
Deferrari, J.O., de Lederkremer, R.M., Matsuhiro, B. & Litter, M.I. (1970) . Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine. Carbohydrate Research, 14(1), 103-107.http://dx.doi.org/10.1016/S0008-6215(00)80704-1
---------- CHICAGO ----------
Deferrari, J.O., de Lederkremer, R.M., Matsuhiro, B., Litter, M.I. "Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine" . Carbohydrate Research 14, no. 1 (1970) : 103-107.http://dx.doi.org/10.1016/S0008-6215(00)80704-1
---------- MLA ----------
Deferrari, J.O., de Lederkremer, R.M., Matsuhiro, B., Litter, M.I. "Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine" . Carbohydrate Research, vol. 14, no. 1, 1970, pp. 103-107.http://dx.doi.org/10.1016/S0008-6215(00)80704-1
---------- VANCOUVER ----------
Deferrari, J.O., de Lederkremer, R.M., Matsuhiro, B., Litter, M.I. Anomalous reaction of d-gluconamide with benzoyl chloride in anhydrous pyridine. Carbohydr. Res. 1970;14(1):103-107.http://dx.doi.org/10.1016/S0008-6215(00)80704-1
