Abstract:
Branched-chain conjugated dienepyranosides including vinyl phosphate esters were subjected to catalytic hydrogenation under different conditions. Heterogeneous catalysts led to isomerization products that were resistant to further hydrogenation. On the other hand, under homogeneous conditions, complete stereoselective hydrogenation was achieved. Methyl 2,4-dideoxy-3-O-diethoxyphosphoryl-4-C-[(methoxycarbonyl)methyl]-α-D-ribo- hexopyranoside (6b), a potential precursor of thromboxane analogs, was obtained.
Registro:
Documento: |
Artículo
|
Título: | Catalytic hydrogenation of phosphate enol esters present in branched chain dienepyranosides in a route to thromboxane analogs from d-galactose |
Autor: | Moradei, O.; Du Mortier, C.M.; Cirelli, A.F.; Thiem, J. |
Filiación: | Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pab. II, 1428 Buenos Aires, Argentina Institut für Organische Chemie, Universität Hamburg, Martin-Luther-King-Platz 6, D-20146 Hamburg, Germany
|
Año: | 1999
|
Volumen: | 18
|
Número: | 1
|
Página de inicio: | 15
|
Página de fin: | 29
|
DOI: |
http://dx.doi.org/10.1080/07328309908543975 |
Título revista: | Journal of Carbohydrate Chemistry
|
Título revista abreviado: | J. Carbohydr. Chem.
|
ISSN: | 07328303
|
CODEN: | JCACD
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07328303_v18_n1_p15_Moradei |
Referencias:
- Vargaftig, B.B., Zirins, P., (1973) Nature (London), 244, p. 114
- Silver, M.J., Smith, J.B., Ingerman, C., Kocsis, J., (1973) Prostaglandins, 4, p. 863
- Gibson, K.H., (1977) Chem. Soc. Rev., 6, p. 489
- Svensson, J., Hamberg, M., Samuelson, B., (1975) Acta Physiol. Scand., 94, p. 222
- Hamberg, M., Samuelson, B., (1974) Proc. Natl. Acad Sci. USA, 71, p. 3400
- Bhagwat, S.S., Hamann, P.R., Still, W.C., Bunting, S., Fitzpatric, F.A., (1985) Nature (London), 315, p. 511
- Bhagwat, S.S., Hamann, P.R., Still, W.C., (1985) J. Am. Chem. Soc., 107, p. 6372
- Hanessian, S., Lavallee, P., (1980) Can. J. Chem., 59, p. 870
- Corey, E.J., Shibasaki, M., Knolle, J., (1977) Tetrahedron Lett., p. 1625
- Pelyvás, I., Lindhorst, T., Thiem, J., (1990) Liebigs Ann. Chem., p. 761
- Kelly, A.G., Roberts, J.S., (1980) J. Chem. Soc., Chem. Commun., p. 228
- Booysen, J.F., Holzapfel, C.W., (1995) Synth. Commun., 25, p. 1461
- Moradei, O., Du Mortier, C., Fernández Cirelli, A., Thiem, J., (1995) J. Carbohydr. Chem., 14, p. 525
- Moradei, O., Du Mortier, C., Fernández Cirelli, A., (1997) Tetrahedron, 53, p. 7397
- Nishimura, S., Sakamoto, H., Ozawa, T., (1973) Chem. Lett., p. 855
- Romo De Vivar, A., Bratoeff, E.A., Ríos, T., (1966) J. Org. Chem., 31, p. 673
- Coates, R., Shah, S., Mason, R., (1982) J. Am. Chem. Soc., 104, p. 2198
- Augustine, R.L., (1963) J. Org. Chem., 28, p. 152
- Rylander, P.N., (1967) Catalytic Hydrogenation over Platinum Metal, , Academic Press, New York
- Lichtenthaler, F.W., (1961) Chem. Rev., 61, p. 607
- Brown, J.M., Naik, R., (1982) J. Chem. Soc., Chem. Commun., p. 348
- Evans, D.A., Morrissey, M.M., (1984) J. Am. Chem. Soc., 106, p. 3866
- Corey, E.J., Desai, M.C., Engler, T.A., (1985) J. Am. Chem. Soc., 107, p. 4339
- Smith A. III, Yokoyama, Y., Huryn, D., Dunlap, N., (1987) Tetrahedron Lett., 28, p. 3659
- Christl, M., Reich, H.J., Roberts, J.D., (1971) J. Am. Chem. Soc., 93, p. 3463
- Roberts, J.D., Weigert, F.J., Kroschwitz, J.J., Reich, H.J., (1970) J. Am. Chem. Soc., 92, p. 1338
- Brown, J.M., Hall, S.A., (1985) Tetrahedron, 41, p. 4639
Citas:
---------- APA ----------
Moradei, O., Du Mortier, C.M., Cirelli, A.F. & Thiem, J.
(1999)
. Catalytic hydrogenation of phosphate enol esters present in branched chain dienepyranosides in a route to thromboxane analogs from d-galactose. Journal of Carbohydrate Chemistry, 18(1), 15-29.
http://dx.doi.org/10.1080/07328309908543975---------- CHICAGO ----------
Moradei, O., Du Mortier, C.M., Cirelli, A.F., Thiem, J.
"Catalytic hydrogenation of phosphate enol esters present in branched chain dienepyranosides in a route to thromboxane analogs from d-galactose"
. Journal of Carbohydrate Chemistry 18, no. 1
(1999) : 15-29.
http://dx.doi.org/10.1080/07328309908543975---------- MLA ----------
Moradei, O., Du Mortier, C.M., Cirelli, A.F., Thiem, J.
"Catalytic hydrogenation of phosphate enol esters present in branched chain dienepyranosides in a route to thromboxane analogs from d-galactose"
. Journal of Carbohydrate Chemistry, vol. 18, no. 1, 1999, pp. 15-29.
http://dx.doi.org/10.1080/07328309908543975---------- VANCOUVER ----------
Moradei, O., Du Mortier, C.M., Cirelli, A.F., Thiem, J. Catalytic hydrogenation of phosphate enol esters present in branched chain dienepyranosides in a route to thromboxane analogs from d-galactose. J. Carbohydr. Chem. 1999;18(1):15-29.
http://dx.doi.org/10.1080/07328309908543975