Artículo
Varela, O.J.; Cirelli, A.F.; De Lederkremer, R.M. "β-Elimination in aldonolactones. the conversion of l-rhamnono-1-5-lactone into 3-benzoyloxy-6-methylpyran-2-one" (1980) Carbohydrate Research. 79(2):219-224
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Abstract:
Benzoylation of l-rhamnono-1,5-lactone (1) for 90 min at room temperature afforded 2,3,4-tri-O-benzoyl-l-rhamnono-I,5-Iactone (2). When an excess of benzoyl chloride and pyridine was used for 20 h, with subsequent sublimation of benzoic acid from the mixture at 120° in vacua, a double elimination took place and 3-benzoyloxy-6-methylpyran-2-one (4) was isolated as the main product. The conversion of 1, 2, and 2,4.-di-O-benzoyl-3,6-dideoxy-l-erythro-hex-2-enono-l,5-lactone (3) into the pyran-one derivative 4 under different conditions was monitored chromatographically. © 1980.
Registro:
| Documento: | Artículo |
| Título: | β-Elimination in aldonolactones. the conversion of l-rhamnono-1-5-lactone into 3-benzoyloxy-6-methylpyran-2-one |
| Autor: | Varela, O.J.; Cirelli, A.F.; De Lederkremer, R.M. |
| Filiación: | Departamento de Quimica Orgánica, Facultad de Ciencas Exactas y Naturales, Universidad de Buenos Aires. Ciudad Univercitaria, Pabellón II, 1428 Buenos Aires, Argentina |
| Año: | 1980 |
| Volumen: | 79 |
| Número: | 2 |
| Página de inicio: | 219 |
| Página de fin: | 224 |
| DOI: | http://dx.doi.org/10.1016/S0008-6215(00)83833-1 |
| Título revista: | Carbohydrate Research |
| Título revista abreviado: | Carbohydr. Res. |
| ISSN: | 00086215 |
| CODEN: | CRBRA |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v79_n2_p219_Varela |
Referencias:
- Lederkremer, Litter, (1971) Carbohydr. Res., 20, pp. 442-444
- Litter, De Lederkremer, (1973) Carbohydr. Res., 26, pp. 431-434
- Litter, De Lederkremer, (1974) An. Asoc. Quim. Argent., 62, pp. 147-150
- De Lederkremer, Litter, Sala, (1974) Carbohydr. Res., 36, pp. 185-187
- Varela, Cirelli, De Lederkremer, (1979) Carbohydr. Res., 70, pp. 27-35
- Nelson, Gratzi, The conversion of d-glucono-1,5-lactone into an α-pyrone derivative (1978) Carbohydrate Research, 60, pp. 267-273
- Sheppard, Turner, (1968) Chem. Commun., pp. 77-78
- Pirkle, Dines, (1969) J. Org. Chem., 34, pp. 2239-2244
- Pirkle, Turner, (1975) J. Org. Chem., 40, pp. 1617-1620
- Nakata, Hirata, Tatematsu, (1965) Tetrahedron Lett., pp. 123-128
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- Nakata, Tatematsu, (1967) Tetrahedron Lett., pp. 4101-4103
- Hudson, Isbell, (1929) J. Am. Chem. Soc., 51, pp. 2225-2229
Citas:
---------- APA ----------
Varela, O.J., Cirelli, A.F. & De Lederkremer, R.M. (1980) . β-Elimination in aldonolactones. the conversion of l-rhamnono-1-5-lactone into 3-benzoyloxy-6-methylpyran-2-one. Carbohydrate Research, 79(2), 219-224.http://dx.doi.org/10.1016/S0008-6215(00)83833-1
---------- CHICAGO ----------
Varela, O.J., Cirelli, A.F., De Lederkremer, R.M. "β-Elimination in aldonolactones. the conversion of l-rhamnono-1-5-lactone into 3-benzoyloxy-6-methylpyran-2-one" . Carbohydrate Research 79, no. 2 (1980) : 219-224.http://dx.doi.org/10.1016/S0008-6215(00)83833-1
---------- MLA ----------
Varela, O.J., Cirelli, A.F., De Lederkremer, R.M. "β-Elimination in aldonolactones. the conversion of l-rhamnono-1-5-lactone into 3-benzoyloxy-6-methylpyran-2-one" . Carbohydrate Research, vol. 79, no. 2, 1980, pp. 219-224.http://dx.doi.org/10.1016/S0008-6215(00)83833-1
---------- VANCOUVER ----------
Varela, O.J., Cirelli, A.F., De Lederkremer, R.M. β-Elimination in aldonolactones. the conversion of l-rhamnono-1-5-lactone into 3-benzoyloxy-6-methylpyran-2-one. Carbohydr. Res. 1980;79(2):219-224.http://dx.doi.org/10.1016/S0008-6215(00)83833-1
