Abstract:
The regioselective introduction of a methoxymethyl (MOM) group on different type of glycols via an orthoester intermediate was investigated. The novelty presented in this study is the use of ceric ammonium nitrate instead of the previously employed camphorsulfonic acid as catalyst. The monoprotection reaction was revealed to be highly selective when the glycol moiety was in the presence of an ether functionality. Graphical abstract © 2004 Elsevier Ltd. All rights reserved.
Registro:
Documento: |
Artículo
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Título: | Cerium ammonium nitrate: A new catalyst for regioselective protection of glycols |
Autor: | Comin, M.J.; Elhalem, E.; Rodriguez, J.B. |
Filiación: | Depto. de Quím. Orgán., Fac. de Ciencias Exactas Y Naturales, Univ. Buenos Aires, Pabellon 2, C., Argentina
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Palabras clave: | Diisobutyl aluminum hydride; Glycols; Methoxymethyl protecting group; Regioselective monoprotection; cerium ammonium nitrate; glycol; nitric acid derivative; unclassified drug; article; catalysis; catalyst; chemical analysis; chemical structure; priority journal; structure analysis |
Año: | 2004
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Volumen: | 60
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Número: | 51
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Página de inicio: | 11851
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Página de fin: | 11860
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DOI: |
http://dx.doi.org/10.1016/j.tet.2004.09.097 |
Título revista: | Tetrahedron
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Título revista abreviado: | Tetrahedron
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ISSN: | 00404020
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CODEN: | TETRA
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v60_n51_p11851_Comin |
Referencias:
- Greene, T.W., Wuts, P.G.M., (1999) Protective Groups in Organic Synthesis, , 3rd ed Wiley New York
- Nicolaou, K.C., Sorensen, E.J., (1996) Classics in Total Synthesis, , VCH Weinheim
- Oikawa, M., Wada, A., Okazaki, F., Kusumoto, S., (1996) J. Org. Chem., 61, pp. 4469-4475
- Bailey, W.F., Zarcone, L.M.J., Rivera, A.D., (1995) J. Org. Chem., 60, pp. 2532-2536
- Ogilvie, K.K., Hakimelahi, G.H., Proba, Z.A., McGee, D.P.C., (1982) Tetrahedron Lett., 23, pp. 1997-2000
- Ogilvie, K.K., McGee, D.P.C., Boisvert, S.M., Hakimelahi, G.H., Proba, Z.A., (1983) Can. J. Chem., 61, pp. 1204-1209
- Chauchan, K., Wheelan, P., Murphy, R.C., Falck, J.R., (1994) J. Am. Chem. Soc., 116, pp. 5050-5056
- Comin, M.J., Leitofuter, J., Rodriguez, J.B., (2002) Tetrahedron, 58, pp. 3129-3136
- Friesen, R.W., Vanderwal, C., (1996) J. Org. Chem., 61, pp. 9103-9110
- Takasu, M., Naruse, Y., Yamamoto, H., (1988) Tetrahedron Lett., 29, pp. 1947-1950
- Sharpless, K.B., Amberg, W., Bennani, Y.L., Crispino, G.A., Hartung, J., Jeong, K.-S., Kwong, H.-L., Zhang, X.-Z., (1992) J. Org. Chem., 57, pp. 2768-2771
- Schvartzapel, A.J., Fichera, L., Esteva, M., Rodriguez, J.B., Gros, E.G., (1995) Helv. Chim. Acta, 78, pp. 1207-1214
- Schvartzapel, A.J., Zhong, L., Docampo, R., Rodriguez, J.B., Gros, E.G., (1997) J. Med. Chem., 40, pp. 2314-2322
- Block, M.H., (1992) Tetrahedron Lett., 33, pp. 8149-8150
- Hajkó, J., Borbás, A., Lipták, A., Kajtár-Peredy, M., (1991) Carbohydr. Res., 216, pp. 413-420
- Borbás, A., Hajkó, J., Kajtár-Peredy, M., Lipták, A., (1993) J. Carbohydr. Chem., 12, pp. 191-200
- Lipták, A., Borbás, A., Jánossy, L., Szilágyi, L., (2000) Tetrahedron Lett., 41, pp. 4949-4953
- Lipták, A., (1976) Tetrahedron Lett., 17, pp. 3551-3554
- Desruet, M.-D., Morin, C., Ogier, L., (1997) Carbohydr. Res., 301, pp. 225-229
- García Fernández, J.M., Ortiz Mellet, C., Moreno Marín, A., Fuentes, J., (1995) Carbohydr. Res., 274, pp. 263-268
- Mashhood, S., Ramesh, K., Borchardt, R.T., (1990) Tetrahedron Lett., 31, pp. 1509-1512
- Holysz, R.P., (1953) J. Am. Chem. Soc., 75, pp. 4432-4437
- Vanrheenen, V., Kelly, R.C., Cha, D.Y., (1976) Tetrahedron Lett., 23, pp. 1973-1976
- Sharpless, K.B., Lauer, R.F., (1973) J. Am. Chem. Soc., 95, pp. 2697-2699
Citas:
---------- APA ----------
Comin, M.J., Elhalem, E. & Rodriguez, J.B.
(2004)
. Cerium ammonium nitrate: A new catalyst for regioselective protection of glycols. Tetrahedron, 60(51), 11851-11860.
http://dx.doi.org/10.1016/j.tet.2004.09.097---------- CHICAGO ----------
Comin, M.J., Elhalem, E., Rodriguez, J.B.
"Cerium ammonium nitrate: A new catalyst for regioselective protection of glycols"
. Tetrahedron 60, no. 51
(2004) : 11851-11860.
http://dx.doi.org/10.1016/j.tet.2004.09.097---------- MLA ----------
Comin, M.J., Elhalem, E., Rodriguez, J.B.
"Cerium ammonium nitrate: A new catalyst for regioselective protection of glycols"
. Tetrahedron, vol. 60, no. 51, 2004, pp. 11851-11860.
http://dx.doi.org/10.1016/j.tet.2004.09.097---------- VANCOUVER ----------
Comin, M.J., Elhalem, E., Rodriguez, J.B. Cerium ammonium nitrate: A new catalyst for regioselective protection of glycols. Tetrahedron. 2004;60(51):11851-11860.
http://dx.doi.org/10.1016/j.tet.2004.09.097