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Abstract:

3a-Acetoxy-5β-cholan-24-oic acid was transformed into 3β-acetoxy-5β-pregnan-20-one by a sequence of reactions that involves inversion of the configuration at C-3 and degradation of the side chain of the bile acid. The procedure would allow the introduction of a label at C-21 of the final compound. © 1984, Walter de Gruyter. All rights reserved.

Registro:

Documento: Artículo
Título:Preparation of 3β -Acetoxy-5β-pregnan-20-one from 3 a- Acetoxy-5β-cholan-24-oic Acid Aimed at the Isotopic Labelling of the Pregnane Side Chain
Autor:Deluca, M.E.; Seldes, A.M.; Garraffo, H.M.; Gros, E.G.
Filiación:Departamento de Quimica Organica y UMYMFOR, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pab. 2, Ciudad Universitaria, 1428, Buenos Aires, Argentina
Palabras clave:3beta acetoxy 5beta pregnan 20 one; drug analysis; drug identification; drug structure; drug synthesis; infrared spectrometry; mass spectrometry; methodology; nonhuman; nuclear magnetic resonance; proton nuclear magnetic resonance; theoretical study
Año:1984
Volumen:39
Número:11
Página de inicio:1617
Página de fin:1621
DOI: http://dx.doi.org/10.1515/znb-1984-1125
Título revista:Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Título revista abreviado:Z. Naturforsch. Sect. B J. Chem. Sci.
ISSN:09320776
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_09320776_v39_n11_p1617_Deluca

Referencias:

  • Galagovsky, L.R., Porto, A.M., Burton, G., Gros, E.G., (1984) Z. Naturforsch., 39c, p. 38. , previous papers cited therein
  • Marker, R.E., Kamm, O., Wittle, E.L., (1937) J. Am. Chem. Soc, 59, p. 1841
  • Ruff, A., Reichstein, T., (1951) Helv. Chim. Acta, 79
  • Wall, M.E., Kenney, H.E., Rothman, E.S., (1955) J. Am. Chem. Soc, 77, p. 5665
  • Reggel, L., Friedman, S., Wender, J., (1958) J. Org. Chem., 23, p. 1136
  • Meystre, C.H., Miescher, K., (1946) Helv. Chim. Acta, 29, p. 33
  • Cocker, J.D., Henbest, H.B., Phillipps, G.H., Slater, G.P., Thomas, D.A., (1965) J. Chem. Soc., 6
  • Lewbart, M.L., Mattox, V.R., (1963) J. Org. Chem., 28, p. 2001
  • Riegel, B., Prout, F.S., (1948) J. Org. Chem., 13, p. 933
  • MacPhillamy, H.B., Scholz, C.R., (1949) J. Biol. Chem., 178, p. 37
  • Lardon, A., (1947) Helv. Chim. Acta, 30, p. 597
  • Ruzicka, L., Plattner, P.A., Balla, G., (1942) Helv. Chim. Acta, 25, p. 65

Citas:

---------- APA ----------
Deluca, M.E., Seldes, A.M., Garraffo, H.M. & Gros, E.G. (1984) . Preparation of 3β -Acetoxy-5β-pregnan-20-one from 3 a- Acetoxy-5β-cholan-24-oic Acid Aimed at the Isotopic Labelling of the Pregnane Side Chain. Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 39(11), 1617-1621.
http://dx.doi.org/10.1515/znb-1984-1125
---------- CHICAGO ----------
Deluca, M.E., Seldes, A.M., Garraffo, H.M., Gros, E.G. "Preparation of 3β -Acetoxy-5β-pregnan-20-one from 3 a- Acetoxy-5β-cholan-24-oic Acid Aimed at the Isotopic Labelling of the Pregnane Side Chain" . Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences 39, no. 11 (1984) : 1617-1621.
http://dx.doi.org/10.1515/znb-1984-1125
---------- MLA ----------
Deluca, M.E., Seldes, A.M., Garraffo, H.M., Gros, E.G. "Preparation of 3β -Acetoxy-5β-pregnan-20-one from 3 a- Acetoxy-5β-cholan-24-oic Acid Aimed at the Isotopic Labelling of the Pregnane Side Chain" . Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, vol. 39, no. 11, 1984, pp. 1617-1621.
http://dx.doi.org/10.1515/znb-1984-1125
---------- VANCOUVER ----------
Deluca, M.E., Seldes, A.M., Garraffo, H.M., Gros, E.G. Preparation of 3β -Acetoxy-5β-pregnan-20-one from 3 a- Acetoxy-5β-cholan-24-oic Acid Aimed at the Isotopic Labelling of the Pregnane Side Chain. Z. Naturforsch. Sect. B J. Chem. Sci. 1984;39(11):1617-1621.
http://dx.doi.org/10.1515/znb-1984-1125