Navegar

Colección

Datos Estadísticas

Artículo

La versión final de este artículo es de uso interno. El editor solo permite incluir en el repositorio el artículo en su versión post-print. Por favor, si usted la posee enviela a
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Pyranosic enuloses were subjected to Horner-Wadsworth-Emmons (HWE) conditions using the enolate of dimethyl(methoxycarbonyl)methyl phosphonate and its ethyl analogue. 3-O-Phosphorylation of the products as well as an unusual stereospecificity were observed. A mechanism involving a phosphonate-phosphate like rearrangement through a five member intermediate followed by benzoate elimination is proposed.

Registro:

Documento: Artículo
Título:Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses
Autor:Moradei, O.M.; Du Mortier, C.M.; Cirelli, A.F.
Filiación:CIHIDECAR Depto. de Quim. Organ., Fac. de Ciencias Exactas y Naturales, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Palabras clave:sugar phosphate; article; carbohydrate synthesis; drug synthesis; in vitro study; methodology; nuclear magnetic resonance spectroscopy; priority journal; reaction analysis; stereochemistry
Año:1997
Volumen:53
Número:22
Página de inicio:7397
Página de fin:7402
DOI: http://dx.doi.org/10.1016/S0040-4020(97)00425-0
Título revista:Tetrahedron
Título revista abreviado:TETRAHEDRON
ISSN:00404020
CODEN:TETRA
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v53_n22_p7397_Moradei

Referencias:

  • Rosenthal, A., Nguyen, L., (1967) Tetrahedron Lett., p. 2393
  • Rosenthal, A., Catsoulacos, P., (1968) Can. J. Chem., 46, p. 2869
  • Moradei, O., Du Mortier, C., Fernández Cirelli, A., Thiem, J., (1995) J. Carbohydr. Chem., 14, p. 525
  • Hanessian, S., Lavallee, P., (1981) Can. J. Chem., 59, p. 870
  • Corey, E.J., Shibasaki, M., Knolle, J., (1977) Tetrahedron Lett., p. 1625
  • Wadsworth W.S., Jr., Emmons, W.D., (1961) J. Am. Chem. Soc., 83, p. 1733
  • Hall, L.D., Malcolm, R.B., (1972) Can. J. Chem., 50, p. 2102
  • Mellema, J., Pieters, J.M.L., Van Der Marel, G.A., Van Boom, J.H., Haasnoot, C.A.G., Altona, C., (1984) Eur. J. Biochem., 143, p. 285
  • Buchanan, G.W., Bowen, J.H., (1977) Can. J. Chem., 55, p. 604
  • Kelly, S.E., (1993) Comprehensive Organic Chemistry, 1, p. 729. , Trost, B. M. and Fleming, J. Ed.; Pergamon Press, Oxford
  • Brimacombe, J.S., Kabir, A.K., (1986) Carbohydr. Res., 150, p. 35
  • Maryanoff, B.E., Reitz, A.B., Mutter, M.S., Inners, R.R., Almond H.R., Jr., Whittle, R.R., Olofson, R.A., (1986) J. Am. Chem. Soc., 108, p. 7664
  • Pudovik, A.N., Zimin, M.G., (1980) Pure Appl. Chem., 52, p. 989
  • Westheimer, F.H., (1968) Acc. Chem. Res., 1, p. 70
  • Thatcher, G.R.J., Kluger, R.H., (1989) Adv. Phys. Org. Chem., 25, p. 99
  • Kluger, R., Taylor, S.D., (1991) J. Am. Chem. Soc., 113, p. 5714
  • Pudovik, A.N., Zimin, M.G., Sobanov, A.A., (1977) Zh. Obshch. Khim., 47, p. 1000
  • Iluminati, G., Mandolini, L., (1981) Acc. Chem. Res., 14, p. 95
  • Mandolini, L., (1986) Adv. Phys. Org. Chem., 22, p. 1
  • Lichtenthaler, F.W., Ogawa, S., Heidel, P., (1977) Chem. Ber., 110, p. 3324
  • Valverde, S., Martin-Lomas, M., Herradón, B., García Ochoa, S., (1987) Tetrahedron, 43, p. 1895
  • Maryanoff, B.E., Reitz, A.B., (1989) Chem. Rev., 89, p. 863
  • Hubert, A.J., Reimlinger, H., (1969) Synthesis, p. 97
  • (1970) Synthesis, p. 405
  • De Puy, C.H., Morris, G.F., Smith, J.S., Smat, R.J., (1965) J. Am. Chem. Soc., 87, p. 242
  • Kaneko, H., Okazaki, M., (1966) Tetrahedron Lett., p. 219
  • Gupta, R.C., Srivastava, S.C., Grover, P.K., Anand, N., (1971) Indian J. Chem., 9, p. 890

Citas:

---------- APA ----------
Moradei, O.M., Du Mortier, C.M. & Cirelli, A.F. (1997) . Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses. Tetrahedron, 53(22), 7397-7402.
http://dx.doi.org/10.1016/S0040-4020(97)00425-0
---------- CHICAGO ----------
Moradei, O.M., Du Mortier, C.M., Cirelli, A.F. "Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses" . Tetrahedron 53, no. 22 (1997) : 7397-7402.
http://dx.doi.org/10.1016/S0040-4020(97)00425-0
---------- MLA ----------
Moradei, O.M., Du Mortier, C.M., Cirelli, A.F. "Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses" . Tetrahedron, vol. 53, no. 22, 1997, pp. 7397-7402.
http://dx.doi.org/10.1016/S0040-4020(97)00425-0
---------- VANCOUVER ----------
Moradei, O.M., Du Mortier, C.M., Cirelli, A.F. Anomalous Horner-Wadsworth-Emmons reactions on 3,4-enuloses. TETRAHEDRON. 1997;53(22):7397-7402.
http://dx.doi.org/10.1016/S0040-4020(97)00425-0