Abstract:
The base‐catalysed rearrangement of 3β, 16α‐dihydroxy‐5α‐androstan‐17‐one diacetate (1) in (D6)benzene/CD3OD to 3β, 17β‐dihydroxy‐5α‐androstan‐16‐one (3) is followed by 13C‐NMR spectroscopy. By the same procedure, it is determined that in (D6)benzene/CD3OD, but under acid catalysis, 1 does not rearrange to 3 but yields the intermediate product 3β, 16α‐dihydroxy‐5α ‐androstan‐17‐one 17α ‐methyl hemiacetal (5). Copyright © 1989 Verlag GmbH & Co. KGaA, Weinheim
Registro:
Documento: |
Artículo
|
Título: | Dissimilar behaviour of 3β, 16α‐dihydroxy‐5α‐androstan‐17‐one Diacetate under Basic and Acidic Conditions |
Autor: | Doller, D.; Gros, E.G. |
Filiación: | Departamento de Quimica Orgánica, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2, Buenos Aires, 1428, Argentina
|
Palabras clave: | 3beta,16alpha dihydroxy 5alpha androstan 17 one diacetate; unclassified drug; carbon nuclear magnetic resonance; drug stability; drug structure; nonhuman; nuclear magnetic resonance |
Año: | 1989
|
Volumen: | 72
|
Número: | 6
|
Página de inicio: | 1241
|
Página de fin: | 1247
|
DOI: |
http://dx.doi.org/10.1002/hlca.19890720608 |
Título revista: | Helvetica Chimica Acta
|
Título revista abreviado: | Helv. Chim. Acta
|
ISSN: | 0018019X
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0018019X_v72_n6_p1241_Doller |
Referencias:
- Kirk, D.N., Hartshorn, M.P., (1968) Steroid Reaction Mechanisms, p. 388. , Elsevier, Amsterdam
- Collins, C.J., Eastham, J.F., (1966) The Chemistry of Carbonyl Compounds, pp. 761-794. , S. Patai, Interscience, New York, Chapt. 15, pp
- Doller, D., Gros, E.G., ; Numazawa, M., Nagaoka, M., Mutsumi, A., (1987) Chem. Pharm. Bull., 35, p. 4763
- Doller, D., Gros, E.G., 13C NMR spectroscopic study of the rearrangement of 16β-hydroxy-17-oxo steroids to 17β-hydroxy-16-oxo isomers (1988) Magnetic Resonance in Chemistry, 26, p. 539
- Fishman, J., (1960) J. Am. Chem. Soc., 82, p. 6143
- Numazawa, M., Nagaoka, M., Osawa, Y., (1982) J. Org. Chem., 47, p. 4024
- Wehrli, F.W., Wirthlin, T., (1980) Interpretation of Carbon‐13 NMR Spectra, pp. 107-110. , Heyden, London
- Hassner, A., Catsoulacos, P., (1966) J. Org. Chem., 31, p. 3149
- Hampel, B., Kraemer, J.M., (1966) Tetrahedron, 22, p. 1601
- v. Demarco, P., Farkas, E., Doddrell, D., Mylari, B.L., Wenkert, E., (1968) J. Am. Chem. Soc., 90, p. 5480
- Cooley, G., Kirk, D.N., Morgan, R.E., Sá e Melo, M.L., (1977), p. 1390. , J. Chem. Soc., Perkin Trans. 1; Bagget, N., (1979) Comprehensive Organic Chemistry. The Synthesis and Reactions of Organic Compounds, 1, pp. 832-834. , D. H. R. Barton, W. D. Ollis, Pergamon, Oxford
- Burkert, U., Allinger, N.L., (1982) Molecular Mechanics, , A. C. S. Monographs 177, Washington, D. C
- Leeds, N.S., Fukushima, D.K., Gallagher, T.F., (1954) J. Am. Chem. Soc., 76, p. 2943
- Johnson, W.S., Gastambide, B., Pappo, R., (1957) J. Am. Chem. Soc., 79, p. 1991
Citas:
---------- APA ----------
Doller, D. & Gros, E.G.
(1989)
. Dissimilar behaviour of 3β, 16α‐dihydroxy‐5α‐androstan‐17‐one Diacetate under Basic and Acidic Conditions. Helvetica Chimica Acta, 72(6), 1241-1247.
http://dx.doi.org/10.1002/hlca.19890720608---------- CHICAGO ----------
Doller, D., Gros, E.G.
"Dissimilar behaviour of 3β, 16α‐dihydroxy‐5α‐androstan‐17‐one Diacetate under Basic and Acidic Conditions"
. Helvetica Chimica Acta 72, no. 6
(1989) : 1241-1247.
http://dx.doi.org/10.1002/hlca.19890720608---------- MLA ----------
Doller, D., Gros, E.G.
"Dissimilar behaviour of 3β, 16α‐dihydroxy‐5α‐androstan‐17‐one Diacetate under Basic and Acidic Conditions"
. Helvetica Chimica Acta, vol. 72, no. 6, 1989, pp. 1241-1247.
http://dx.doi.org/10.1002/hlca.19890720608---------- VANCOUVER ----------
Doller, D., Gros, E.G. Dissimilar behaviour of 3β, 16α‐dihydroxy‐5α‐androstan‐17‐one Diacetate under Basic and Acidic Conditions. Helv. Chim. Acta. 1989;72(6):1241-1247.
http://dx.doi.org/10.1002/hlca.19890720608