Artículo
Abstract:
Regioselective silylation of D-ribono- 1,4-lactone (1) with 1.1 molar equivalents of tert-butylchlorodiphenylsilane led to the 5-O-silyl derivative 2 (72% yield). The free HO-2 and HO-3 of 2 were acetylated or benzoylated to give the derivatives 3 and 4, respectively, in almost quantitative yield. The Sml2-promoted elimination of the 2,3-acyloxy groups was applied to 3 and 4. It was proved that the silyloxy group was stable under the reaction conditions, and the butenolide 5 (5-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-glycero-pent-2-eno-1,4-lactone) was obtained in over 50% yield, from both 3 and 4. In order to establish its optical purity, compound 5 was hydrogenated and O-desilylated to the (5)-4-hydroxymethyl-1,4-butyrolactone (6). Alternatively, enantiomerically pure compound 6 was prepared from L-glutamic acid. The optical rotations of 6 from both preparations were very coincident, indicating high optical purity (ee > 95%) for the butenolide 5.
Registro:
| Documento: | Artículo |
| Título: | Sml2 promoted elimination in 5-O-silyl derivatives of D-ribono-1,4-lactone |
| Autor: | Zunszain, P.A.; Varela, O. |
| Filiación: | CIHIDECAR (CONICET), Departamento de Química Orgánica, Pabellón 2, 1428 Buenos Aires, Argentina |
| Año: | 1998 |
| Volumen: | 86 |
| Número: | 3-6 |
| Página de inicio: | 151 |
| Página de fin: | 155 |
| Título revista: | Anales des la Asociacion Quimica Argentina |
| ISSN: | 03650375 |
| Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p151_Zunszain |
Referencias:
- De Lederkremer, R.M., Varela, O., (1994) Adv. Carbohydr. Chem. Biochem., 50, p. 125
- Hanessian, S., Murray, P.J., (1987) Fetrahedron, 43, p. 5055
- Camps, P., Cardelach, J., Font, J., Ortuño, R.M., Ponsati, O., (1982) Tetrahedron, 38, p. 2402
- Hanessian, S., Bargiotti, A., Larue, M., (1978) Tetrahedron Lett., p. 737
- Ireland, R.E., Anderson, R.C., Badoud, R., Fitzsimmons, B.J., McGarvey, G.J., Thaisrivongs, S., Wilcox, C.S., (1983) J. Am. Chem. Soc., 105, p. 1988
- Vekemans, J.A.J.M., Franken, G.A.M., Dapperens, C.W.M., Godefroi, E.F., Chittenden, G.J.F., (1988) J. Org. Chem., 53, p. 627
- Hanessian, S., Girard, C., Chiara, J.L., (1992) Tetrahedron Lett., 33, p. 573
- Garegg, P.J., Samuelsson, B., Synthesis, 469, p. 1979
- Inanaga, J., Katsuki, J., Yamaguchi, M., (1991) Chem. Lett., p. 1025
- Fukuzawa, S., Nakanishi, A., Fujinami, T., Sakai, S., (1988) J. Chem. Soc. Perkin Trans I, p. 1669
- Ravid, U., Silverstein, R.M., Smith, L.R., (1978) Tetrahedron, 34, p. 1449
Citas:
---------- APA ----------
Zunszain, P.A. & Varela, O. (1998) . Sml2 promoted elimination in 5-O-silyl derivatives of D-ribono-1,4-lactone. Anales des la Asociacion Quimica Argentina, 86(3-6), 151-155.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p151_Zunszain [ ]
---------- CHICAGO ----------
Zunszain, P.A., Varela, O. "Sml2 promoted elimination in 5-O-silyl derivatives of D-ribono-1,4-lactone" . Anales des la Asociacion Quimica Argentina 86, no. 3-6 (1998) : 151-155.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p151_Zunszain [ ]
---------- MLA ----------
Zunszain, P.A., Varela, O. "Sml2 promoted elimination in 5-O-silyl derivatives of D-ribono-1,4-lactone" . Anales des la Asociacion Quimica Argentina, vol. 86, no. 3-6, 1998, pp. 151-155.Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p151_Zunszain [ ]
---------- VANCOUVER ----------
Zunszain, P.A., Varela, O. Sml2 promoted elimination in 5-O-silyl derivatives of D-ribono-1,4-lactone. 1998;86(3-6):151-155.Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p151_Zunszain [ ]
