Abstract:
3β,20S-dihydroxycholest-5-en-23-one 3-triethylammonium sulfate was synthesized from pregnenolone. The introduction of the side chain was accomplished by Mukaiyama cross-aldol reaction of 3β-formyloxypregnenolone with 4-methyl-2-trimethylsilyloxy-1-pentene. After formate ester deprotection under very mild conditions, sulfation at position 3 was easily carried out with sulfur trioxide-triethylamine complex.
Registro:
Documento: |
Artículo
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Título: | Synthesis of 3β, 20S-dihydroxycholest-5-en-23-one 3-triethylammonium sulfate |
Autor: | Comin, M.J.; Maier, M.S. |
Filiación: | Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Ciudad Universitaria, 1428 Buenos Aires, Argentina
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Año: | 1998
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Volumen: | 86
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Número: | 3-6
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Página de inicio: | 117
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Página de fin: | 122
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Título revista: | Anales des la Asociacion Quimica Argentina
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ISSN: | 03650375
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p117_Comin |
Referencias:
- D'Auria, M.V., Minale, L., Riccio, R., (1993) Chem. Rev., 93, p. 1839
- Honda, M., Komori, T., (1986) Tetrahedron Lett., 27, p. 3369
- Mukaiyama, T., Banno, K., Narasaka, K., (1974) J. Am. Chem. Soc., 96, p. 7503
- Honda, M., Ingarashi, T., Komori, T., (1990) Liebigs Ann. Chem., p. 547
- McKee, T.C., Cardellina, J.H., Riccio, R., D'Auria, M.V., Iorizzi, M., Minale, L., Moran, R.A., Boyd, M.R., (1994) J. Med. Chem., 37, p. 793
- Roccatagliata, A.J., Maier, M.S., Seldes, A.M., Pujol, C.A., Damonte, E.B., (1996) J. Nat. Prod., 59, p. 887
- Pérez, M.G., Maier, M.S., (1995) Tetrahedron Lett., 36, p. 3311
- Baldessari, A., Maier, M.S., Gros, E.G., (1995) Tetrahedron Lett., 36, p. 4349
- Tserng, K.-Y., Klein, P.D., (1977) J. Lipid Res., 18, p. 491
- Zemlicka, J., Beránck, J., Smrt, J., (1962) Collection Czecholslov Chem. Comm., 27, p. 2784
- Jung, M.E., McCombs, C.A., Takeda, Y., Pan, Y., (1981) J. Am. Chem. Soc., 103, p. 6677
- Blunt, J.W., Stothers, J.B., (1977) Org. Magn. Reson., 9, p. 439
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Citas:
---------- APA ----------
Comin, M.J. & Maier, M.S.
(1998)
. Synthesis of 3β, 20S-dihydroxycholest-5-en-23-one 3-triethylammonium sulfate. Anales des la Asociacion Quimica Argentina, 86(3-6), 117-122.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p117_Comin [ ]
---------- CHICAGO ----------
Comin, M.J., Maier, M.S.
"Synthesis of 3β, 20S-dihydroxycholest-5-en-23-one 3-triethylammonium sulfate"
. Anales des la Asociacion Quimica Argentina 86, no. 3-6
(1998) : 117-122.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p117_Comin [ ]
---------- MLA ----------
Comin, M.J., Maier, M.S.
"Synthesis of 3β, 20S-dihydroxycholest-5-en-23-one 3-triethylammonium sulfate"
. Anales des la Asociacion Quimica Argentina, vol. 86, no. 3-6, 1998, pp. 117-122.
Recuperado de https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p117_Comin [ ]
---------- VANCOUVER ----------
Comin, M.J., Maier, M.S. Synthesis of 3β, 20S-dihydroxycholest-5-en-23-one 3-triethylammonium sulfate. 1998;86(3-6):117-122.
Available from: https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_03650375_v86_n3-6_p117_Comin [ ]