Abstract:
13C NMR spectra for 23 3‐substituted‐5β‐steroidal derivatives have been obtained and individual resonances assigned. The different chemical shifts due to conformational and side chain changes are rationalized in terms of steric interactions. From these results a preferred is conformer is proposed for the cholanoic acid side chain derivatives in solution. Copyright © 1986 John Wiley & Sons, Ltd.
Registro:
Documento: |
Artículo
|
Título: | Studies on the conformations in solution of 5β‐steroids having different side chains by 13C NMR spectroscopy |
Autor: | Seldes, A.M.; Deluca, M.E.; Gros, E.G. |
Filiación: | Departamento de Quimica Orgànica Y Umymfor, Facultad de Ciencias Exactas Y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pab. 2, Buenos Aires, 1428, Argentina
|
Año: | 1986
|
Volumen: | 24
|
Número: | 3
|
Página de inicio: | 185
|
Página de fin: | 189
|
DOI: |
http://dx.doi.org/10.1002/mrc.1260240302 |
Título revista: | Magnetic Resonance in Chemistry
|
Título revista abreviado: | Magn. Reson. Chem.
|
ISSN: | 07491581
|
Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_07491581_v24_n3_p185_Seldes |
Referencias:
- Deluca, M.E., Seldes, A.M., Garraffo, H.M., Gros, E.G., (1984) Z. Naturforsch., Teil B, 39, p. 1617
- Engelhardt, G., Zeigan, D., Schönecker, B., 3C-NMR-Untersuchungen an Steroiden, III. Sterische Effekte von 2,3-substituierten Cholestanderivaten und deren Anwendung zur Konfigurationsbestimmung (1978) J. Prakt. Chem., 320, p. 377
- Blunt, J.W., Stothers, J.B., 13C n.m.r. spectra of steroids —a survey and commentary (1977) Organic Magnetic Resonance, 9, p. 439
- Tori, K., Ishii, H., Wolkowski, Z.W., Chachaty, C., Sangaré, M., Piriou, F., Lukacs, G., (1973), p. 1077. , Tetrahedron Lett; Leibfritz, D., Roberts, J.D., (1973) J. Am. Chem. Soc., 95, p. 4996
- Beierbeck, H., Saunders, J.K., ApSimon, J.W., The semiempirical derivation of13C nuclear magnetic resonance chemical shifts. Hydrocarbons, alcohols, amines, ketones, and olefins (1977) Canadian Journal of Chemistry, 55, p. 2813
- Beierbeck, H., Saunders, J.K., (1976) Can. J. Chem., 54, p. 2985
- Eggert, H., van Antwerp, C.L., Bhacca, N.S., Djerassi, C., (1976) J. Org. Chem., 41, p. 71
- Reich, H.J., Jautelat, M., Messe, M.T., Weigert, F.J., Roberts, J.D., (1969) J. Am. Chem. Soc., 91, p. 7445
- Wellman, K.M., Djerassi, C., (1965) J. Am. Chem. Soc., 87, p. 60
- Duax, W.L., Griffin, J.F., Rohrer, D.C., (1981) J. Am. Chem. Soc., 103, p. 6705
- Gonzàlez, M.D., Burton, G., A carbon-13 nuclear magnetic resonance study of the 1,4-diene analogues of steroid hormones and related steroids (1984) Organic Magnetic Resonance, 22, p. 586
- Romers, C., Altona, C., Jacobs, H.J.C., De Graaff, R.A.G., (1974), in Terpenoids and Steroids, Specialist Periodical Reports, Vol. 4. Chemical Society, London; Trachtenberg, E.N., Byon, C., Gut, M., (1977) J. Am. Chem. Soc., 99, p. 6145
- Maier, M.S., Seldes, A.M., Gros, E.G., ; Lee, H., Bhacca, N.S., Wolff, M.E., (1966) J. Org. Chem., 31, p. 2692
- Lee, H., Wolff, M.E., (1967) J. Org. Chem., 32, p. 192
- Altona, C., Hirschmann, H., (1970) Tetrahedron, 26, p. 2173
- Sato, Y., Basic Bile Acids. II. On the Synthesis and Properties of 39-Aminocholanic Acid and its Derivatives (1963) Nippon kagaku zassi, 84, p. 829
- Bowers, A., Halsall, T.G., Jones, E.R.H., Lemin, A.J., (1953), p. 2555. , J. Chem. Soc; Chang, F.C., Blickenstaff, R.T., Feldstein, A., Gray, J.R., McCaleb, G.S., Sprunt, D.H., (1957) J. Am. Chem. Soc., 79, p. 2164
- Chang, F.C., Blickenstaff, R.T., (1958) J. Am. Chem. Soc., 80, p. 2906
- Blickenstaff, R.T., Chang, F.C., (1958) J. Am. Chem. Soc., 80, p. 2726
- Fieser, L.F., Ettorre, R., (1953) J. Am. Chem. Soc., 75, p. 1700
Citas:
---------- APA ----------
Seldes, A.M., Deluca, M.E. & Gros, E.G.
(1986)
. Studies on the conformations in solution of 5β‐steroids having different side chains by 13C NMR spectroscopy. Magnetic Resonance in Chemistry, 24(3), 185-189.
http://dx.doi.org/10.1002/mrc.1260240302---------- CHICAGO ----------
Seldes, A.M., Deluca, M.E., Gros, E.G.
"Studies on the conformations in solution of 5β‐steroids having different side chains by 13C NMR spectroscopy"
. Magnetic Resonance in Chemistry 24, no. 3
(1986) : 185-189.
http://dx.doi.org/10.1002/mrc.1260240302---------- MLA ----------
Seldes, A.M., Deluca, M.E., Gros, E.G.
"Studies on the conformations in solution of 5β‐steroids having different side chains by 13C NMR spectroscopy"
. Magnetic Resonance in Chemistry, vol. 24, no. 3, 1986, pp. 185-189.
http://dx.doi.org/10.1002/mrc.1260240302---------- VANCOUVER ----------
Seldes, A.M., Deluca, M.E., Gros, E.G. Studies on the conformations in solution of 5β‐steroids having different side chains by 13C NMR spectroscopy. Magn. Reson. Chem. 1986;24(3):185-189.
http://dx.doi.org/10.1002/mrc.1260240302