Synthesis of 3β-hydroxy-5-cholenic acid from 3β-hydroxy-5-pregnen-20-one aimed at the preparation of labelled steroid compounds
3β-Hydroxy-5-cholenic acid was synthesized from 3β-hydroxy-5-pregnen-20-one in nine steps. The procedure would permit the labelling of C-22, C-23, and/or C-24 of the bile-acid side chain by choice of the appropriate labelled reagent. © 1977.
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| Lenguaje: | Inglés |
| Publicado: |
1977
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 06096caa a22008777a 4500 | ||
|---|---|---|---|
| 001 | PAPER-12325 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518204232.0 | ||
| 008 | 190411s1977 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0017625989 | |
| 024 | 7 | |2 cas |a carbon, 7440-44-0; pregnenolone, 145-13-1; Carbon Radioisotopes; Cholenes; Pregnenolone, 145-13-1; Sterols | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a JSTBB | ||
| 100 | 1 | |a Burton, G. | |
| 245 | 1 | 0 | |a Synthesis of 3β-hydroxy-5-cholenic acid from 3β-hydroxy-5-pregnen-20-one aimed at the preparation of labelled steroid compounds |
| 260 | |c 1977 | ||
| 270 | 1 | 0 | |m Gros, E.G.; Departamento de Quimica Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a Ruzicka, Wettstein, Sexualhormone V. K�nstliche Herstellung des m�nnlichen Sexualhormons trans-Dehydro-androsteron und des Androsten-3,17-dions (1935) Helvetica Chimica Acta, 18, pp. 986-994 | ||
| 504 | |a Kučera, Šorm, Über steroide XXIX. Die isolierung von 3β-hydroxy-Δ5-nor-cholensäure und 3β-hydroxy-Δ5-cholestensäure-(26) aus den oxydationsprodukten des 3β-acetoxy-5α,6β-dibromcholestans mit chromtrioxyd (1958) Collection of Czechoslovak Chemical Communications, 23, pp. 116-124 | ||
| 504 | |a Riegel, Kaye, (1944) J. Am. chem. Soc., 66, pp. 723-724 | ||
| 504 | |a Meystre, Frey, Neher, Wettstein, Miescher, �ber Steroide. 48. Mitteilung. Ein einfacher Abbau der Gallens�uren-Seitenkette V. Die �berf�hrung von ?5-3 ?-Oxy-cholens�ure in Pregnenolon und Progesteron (1946) Helvetica Chimica Acta, 29, pp. 627-634 | ||
| 504 | |a Meystre, Wettstein, Miescher, �ber Steroide. (64. Mitteilung). Ein einfacher Abbau der Gallens�uren-Seitenkette VII. Weitere Wege zur Herstellung von Progesteron (1947) Helvetica Chimica Acta, 30, pp. 1022-1027 | ||
| 504 | |a Levin, Mclntosh, Jr., Spero, Rayman, Meinzer, (1948) J. Am. chem. Soc., 70, pp. 511-514 | ||
| 504 | |a Joly, Sauer, Bonner, Preparation of cholesterol-25-3H (1969) Journal of Labelled Compounds, 5, pp. 80-85 | ||
| 504 | |a Fieser, Fieser, (1959) Steroids, p. 509. , Reinhold, New York | ||
| 504 | |a Bergstrom, Pääbo, Preparation of 3beta-Hydroxychol-5-enic Acid from Hyodesoxycholic Acid and Corresponding 24-14C-Labelled Acids. Bile Acids and Steroids 24. (1955) Acta Chemica Scandinavica, 9, pp. 699-701 | ||
| 504 | |a Porto, Baralle, Gros, (1972) J. steroid Biochem., 3, pp. 11-17 | ||
| 504 | |a Colonna, Gros, (1973) J. steroid Biochem., 4, pp. 171-179 | ||
| 504 | |a Chaudhuri, Williams, Nickolson, Gut, (1969) J. org. Chem., 34, pp. 3759-3766 | ||
| 504 | |a Scheineider, (1972) Tetrahedron, 28, pp. 2717-2726 | ||
| 504 | |a Narwid, Cooney, Uskokovic, (1974) Helv. chim. Acta, 57, pp. 771-781 | ||
| 504 | |a Faulkner, Stereoselective Synthesis of Trisubstituted Olefins (1971) Synthesis, pp. 175-189 | ||
| 504 | |a Letourneux, Lo, Chaudhuri, Gut, Acid-catalyzed rearrangement of 20-vinylpregn-5-ene-3.beta.,20-diol 3-acetate (1975) The Journal of Organic Chemistry, 40, pp. 516-518 | ||
| 504 | |a Sucrow, Inhaltsstoffe vonMomordica charantia L., I. Δ5.25-Stigmastadienol-(3β) und sein β-D-Glucosid (1966) Chemische Berichte, 99, pp. 2765-2777 | ||
| 504 | |a Dasgupta, Crump, Gut, (1974) J. org. Chem., 39, pp. 1658-1662 | ||
| 504 | |a Wicha, Bal, Synthesis of 25-hydroxycholesterol from 3?-hydroxyandrost-5-en-17-one. A method for stereospecific construction of a sterol side-chain (1975) Journal of the Chemical Society, Chemical Communications, pp. 968-969 | ||
| 504 | |a Monson, (1972) Advanced Organic Synthesis, p. 45. , Academic Press, New York | ||
| 504 | |a Monson, (1972) Advanced Organic Synthesis, p. 140. , Academic Press, New York | ||
| 504 | |a Hachey, Szczepanik, Berngruber, Klein, (1973) J. Label Compds., 9, pp. 703-719 | ||
| 504 | |a Porto, Gros, Synthesis of PREGN-5-en-3β-o1-20-one-20-14C (1968) Journal of Labelled Compounds, 4, pp. 276-278 | ||
| 520 | 3 | |a 3β-Hydroxy-5-cholenic acid was synthesized from 3β-hydroxy-5-pregnen-20-one in nine steps. The procedure would permit the labelling of C-22, C-23, and/or C-24 of the bile-acid side chain by choice of the appropriate labelled reagent. © 1977. |l eng | |
| 593 | |a Departamento de Quimica Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina | ||
| 650 | 1 | 7 | |2 spines |a CARBON |
| 690 | 1 | 0 | |a CHOLANE DERIVATIVE |
| 690 | 1 | 0 | |a PREGNENOLONE |
| 690 | 1 | 0 | |a STEROL |
| 690 | 1 | 0 | |a RADIOISOTOPE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a INFRARED SPECTROPHOTOMETRY |
| 690 | 1 | 0 | |a ISOTOPE LABELING |
| 690 | 1 | 0 | |a METHODOLOGY |
| 690 | 1 | 0 | |a NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a OPTICAL ROTATION |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a 3BETA HYDROXYCHOLENIC ACID |
| 690 | 1 | 0 | |a IN VITRO STUDY |
| 690 | 1 | 0 | |a STEROIDOGENESIS |
| 690 | 1 | 0 | |a THEORETICAL STUDY |
| 690 | 1 | 0 | |a CARBON RADIOISOTOPES |
| 690 | 1 | 0 | |a CHOLENES |
| 690 | 1 | 0 | |a ISOTOPE LABELING |
| 690 | 1 | 0 | |a MAGNETIC RESONANCE SPECTROSCOPY |
| 690 | 1 | 0 | |a OPTICAL ROTATION |
| 690 | 1 | 0 | |a PREGNENOLONE |
| 690 | 1 | 0 | |a SPECTROPHOTOMETRY, INFRARED |
| 690 | 1 | 0 | |a STEROLS |
| 700 | 1 | |a Gros, E.G. | |
| 773 | 0 | |d 1977 |g v. 8 |h pp. 69-72 |k n. 1 |p J. Steroid Biochem. |x 00224731 |t Journal of Steroid Biochemistry | |
| 856 | 4 | 1 | |u https://www.scopus.com/inward/record.uri?eid=2-s2.0-0017625989&doi=10.1016%2f0022-4731%2877%2990219-9&partnerID=40&md5=1ebb3762458fea3ff89aba3debde4654 |y Registro en Scopus |
| 856 | 4 | 0 | |u https://doi.org/10.1016/0022-4731(77)90219-9 |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00224731_v8_n1_p69_Burton |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00224731_v8_n1_p69_Burton |y Registro en la Biblioteca Digital |
| 961 | |a paper_00224731_v8_n1_p69_Burton |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 999 | |c 73278 | ||