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Abstract:

[24-14C]-Cholesterol was synthesized by reaction between the phosphorane derivative of [1-14C]-isobutyltriphenylphosphonium bromide and 3β-acetoxy-24-norchola-5,20(22)-dien-23-al (IX) followed by hydrogenation of the condensation product. The intermediate IX was prepared by two different procedures both starting from pregnenolone acetate. © 1973.

Registro:

Documento: Artículo
Título:Synthesis of 3/gb-acetoxy-24-norchola-5,20(22)-dien-23-al. a new intermediate for an improved synthesis of [24-14c]-cholesterol
Autor:Colonna, A.O.; Gros, E.G.
Filiación:Departamento de Qu/'imica Org, 'anica. Facultad de Ciencias Exactas, Naturales. Universidad de Buenos Aires, Pab. 2, Ciudad Universitaria. Buenos Aires, Argentina
Palabras clave:aldehyde; carbon; cholane derivative; cholesterol; norsteroid; pregnenolone; article; chemistry; hydrogenation; isotope labeling; synthesis; Aldehydes; Carbon Isotopes; Chemistry; Cholanes; Cholesterol; Hydrogenation; Isotope Labeling; Norsteroids; Pregnenolone
Año:1973
Volumen:4
Número:2
Página de inicio:171
Página de fin:179
DOI: http://dx.doi.org/10.1016/0022-4731(73)90023-X
Título revista:Journal of Steroid Biochemistry
Título revista abreviado:J. Steroid Biochem.
ISSN:00224731
CODEN:JSTBB
CAS:carbon, 7440-44-0; cholesterol, 57-88-5; pregnenolone, 145-13-1; Aldehydes; Carbon Isotopes; Cholanes; Cholesterol, 57-88-5; Norsteroids; Pregnenolone, 145-13-1
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00224731_v4_n2_p171_Colonna

Referencias:

  • Tschesche, Brassat, (1965) Z. Naturforch., 20 b, p. 707
  • Porto, Gros, (1970) Experientia, 26, p. 11
  • Heftmann, (1970) Steroid Biochemistry, p. 85. , Academic Press, New York
  • Porto, Gros, (1971) Experientia, 27, p. 506
  • Porto, Baralle, Gros, (1972) J. steroid Biochem., 3, p. 11
  • Chen, Osuch, (1969) Biochem. Pharmacol., 18, p. 1797
  • Kurath, Ganis, Radakowich, Cholesterin-[24-14C] (1957) Helvetica Chimica Acta, 40, p. 933
  • Ruzicka, Plattner, Pataki, (1942) Helv. chim. Acta, 25, p. 425
  • Koechlin, Reichstein, �ber Bestandteile der Nebennierenrinde und verwandte Stoffe. (67. Mitteilung). Versuche zur Bereitung von �tiocholandiol-(3 ?, 12 ?)-on-17 durch systematischen Abbau (1944) Helvetica Chimica Acta, 27, p. 549
  • Fieser, Fieser, (1967) Reagents for Organic Synthesis, p. 637. , Wiley, New York
  • Rabjohn, Organic Syntheses (1963) Coll., 4, p. 749. , Wiley, New York
  • Ehrenstein, (1939) J. Org. Chem., 4, p. 506
  • Nystrom, Brown, (1947) J. Am. Chem. Soc., 69, p. 2548
  • Blatt, Organic Syntheses (1943) Coll., 2, p. 358. , Wiley, New York
  • Fagerlund, Idler, (1957) J. Am. Chem. Soc., 79, p. 6473

Citas:

---------- APA ----------
Colonna, A.O. & Gros, E.G. (1973) . Synthesis of 3/gb-acetoxy-24-norchola-5,20(22)-dien-23-al. a new intermediate for an improved synthesis of [24-14c]-cholesterol. Journal of Steroid Biochemistry, 4(2), 171-179.
http://dx.doi.org/10.1016/0022-4731(73)90023-X
---------- CHICAGO ----------
Colonna, A.O., Gros, E.G. "Synthesis of 3/gb-acetoxy-24-norchola-5,20(22)-dien-23-al. a new intermediate for an improved synthesis of [24-14c]-cholesterol" . Journal of Steroid Biochemistry 4, no. 2 (1973) : 171-179.
http://dx.doi.org/10.1016/0022-4731(73)90023-X
---------- MLA ----------
Colonna, A.O., Gros, E.G. "Synthesis of 3/gb-acetoxy-24-norchola-5,20(22)-dien-23-al. a new intermediate for an improved synthesis of [24-14c]-cholesterol" . Journal of Steroid Biochemistry, vol. 4, no. 2, 1973, pp. 171-179.
http://dx.doi.org/10.1016/0022-4731(73)90023-X
---------- VANCOUVER ----------
Colonna, A.O., Gros, E.G. Synthesis of 3/gb-acetoxy-24-norchola-5,20(22)-dien-23-al. a new intermediate for an improved synthesis of [24-14c]-cholesterol. J. Steroid Biochem. 1973;4(2):171-179.
http://dx.doi.org/10.1016/0022-4731(73)90023-X