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Volumn 69, Issue 13-14, 2004, Pages 789-794

Clemmensen reduction of diosgenin and kryptogenin: Synthesis of [16,16,22,22,23,23- 2H 6]-(25R)-26-hydroxycholesterol

Author keywords

26 Hydroxycholesterol; Cholesterol metabolism; Clemmensen reduction; Deuterated isotopomers; Diosgenin; Kryptogenin

Indexed keywords

CHOLESTEROL DERIVATIVE; DEUTERIUM; DIOSGENIN; ISOPRENOID; KRYPTOGENIN; UNCLASSIFIED DRUG;

EID: 9944239289     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2004.09.009     Document Type: Article
Times cited : (18)

References (18)
  • 1
    • 0026551710 scopus 로고
    • Mechanism of degradation of the steroid side chain in the formation of bile acids
    • I. Bjoerkhem Mechanism of degradation of the steroid side chain in the formation of bile acids J Lipid Res 33 1992 455 471
    • (1992) J Lipid Res , vol.33 , pp. 455-471
    • Bjoerkhem, I.1
  • 2
    • 0028584429 scopus 로고
    • Bile acid synthesis from cholesterol: Regulatory and auxiliary pathways
    • N.B. Javitt Bile acid synthesis from cholesterol: regulatory and auxiliary pathways FASEB J 8 1994 1308 1311
    • (1994) FASEB J , vol.8 , pp. 1308-1311
    • Javitt, N.B.1
  • 3
    • 11944268807 scopus 로고
    • Role of oxysteroids in the regulation of cholesterol homeostasis: A critical evaluation
    • E. Lund, and I. Bjorkhem Role of oxysteroids in the regulation of cholesterol homeostasis: a critical evaluation Acc Chem Res 28 1995 241 249
    • (1995) Acc Chem Res , vol.28 , pp. 241-249
    • Lund, E.1    Bjorkhem, I.2
  • 4
    • 0032769495 scopus 로고    scopus 로고
    • The role of oxysteroids in cholesterol homeostasis
    • G. Wolf The role of oxysteroids in cholesterol homeostasis Nutr Rev 57 1999 196 198
    • (1999) Nutr Rev , vol.57 , pp. 196-198
    • Wolf, G.1
  • 5
    • 0020467009 scopus 로고
    • DNA synthesis and 3-hydroxy-3-methylglutaryl CoA reductase activity in PHA-stimulated human lymphocytes: A comparative study of some oxysterols with special reference to side chain hydroxylated derivatives
    • R. Defray, M.E. Astruc, S. Roussillion, B. Descomps, and A. Crastes de Paulet DNA synthesis and 3-hydroxy-3-methylglutaryl CoA reductase activity in PHA-stimulated human lymphocytes: a comparative study of some oxysterols with special reference to side chain hydroxylated derivatives Biochem Biophys Res Commun 106 1982 362 372
    • (1982) Biochem Biophys Res Commun , vol.106 , pp. 362-372
    • Defray, R.1    Astruc, M.E.2    Roussillion, S.3    Descomps, B.4    Crastes De Paulet, A.5
  • 7
    • 0032769064 scopus 로고    scopus 로고
    • 27-hydroxycholesterol: Production rates in normal human subjects
    • W.C. Duane, and N.B. Javitt 27-hydroxycholesterol: production rates in normal human subjects J Lipid Res 40 1999 1194 1199
    • (1999) J Lipid Res , vol.40 , pp. 1194-1199
    • Duane, W.C.1    Javitt, N.B.2
  • 8
    • 0037330693 scopus 로고    scopus 로고
    • 4]-3β-(tert- butyldimethylsilanyloxy)-20-methyl-pregn-5-en-21-ol, a useful intermediate for the preparation of deuterated isotopomers of sterols
    • 4]-3β-(tert- butyldimethylsilanyloxy)-20-methyl-pregn-5-en-21-ol, a useful intermediate for the preparation of deuterated isotopomers of sterols Steroids 68 2003 193 198
    • (2003) Steroids , vol.68 , pp. 193-198
    • Ciuffreda, P.1    Casati, S.2    Bollini, D.3    Santaniello, E.4
  • 9
    • 0242624541 scopus 로고    scopus 로고
    • Synthesis of deuterated isotopomers of 7α and (25 R,S)-26-hydroxycholesterol, internal standards for in vivo determination of the two biosynthetic pathways of bile acids
    • P. Ciuffreda, S. Casati, L. Alessandrini, G. Terraneo, and E. Santaniello Synthesis of deuterated isotopomers of 7α and (25 R,S)-26- hydroxycholesterol, internal standards for in vivo determination of the two biosynthetic pathways of bile acids Steroids 68 2003 733 738
    • (2003) Steroids , vol.68 , pp. 733-738
    • Ciuffreda, P.1    Casati, S.2    Alessandrini, L.3    Terraneo, G.4    Santaniello, E.5
  • 11
    • 0027339734 scopus 로고
    • Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium labeled analogs
    • J. Shoda, M. Axelson, and J. Sjoevall Synthesis of potential C27-intermediates in bile acid biosynthesis and their deuterium labeled analogs Steroids 58 1993 119 125
    • (1993) Steroids , vol.58 , pp. 119-125
    • Shoda, J.1    Axelson, M.2    Sjoevall, J.3
  • 12
    • 0000888971 scopus 로고
    • Synthesis of 26-halo-26-(phenylseleno)- and 26-indolylcholesterol analogues
    • T. Arunachalam, P.J. MacKoul, N.M. Green, and E. Caspi Synthesis of 26-halo-26-(phenylseleno)- and 26-indolylcholesterol analogues J Org Chem 46 1981 2966 2968
    • (1981) J Org Chem , vol.46 , pp. 2966-2968
    • Arunachalam, T.1    MacKoul, P.J.2    Green, N.M.3    Caspi, E.4
  • 13
    • 0027212186 scopus 로고
    • A revisitation of the Clemmensen reduction of diosgenin. Characterization of by-products and their use in the preparation of (25R)-26-hydroxysterols
    • Y. Ni, H-S. Kim, W.K. Wilson, A. Kisic, and GJ. Schroepfer Jr. A revisitation of the Clemmensen reduction of diosgenin. Characterization of by-products and their use in the preparation of (25R)-26-hydroxysterols Tetrahedron Lett 34 1993 3687 3690
    • (1993) Tetrahedron Lett , vol.34 , pp. 3687-3690
    • Ni, Y.1    Kim, H.-S.2    Wilson, W.K.3    Kisic, A.4    Schroepfer Jr., G.J.5
  • 14
    • 0020051430 scopus 로고
    • Cholest-5-ene-3β, 26-diol: Synthesis and biomedical use of a deuterated compound
    • N.B. Javitt, E. Kok, J. Lloyd, A. Benscath, and F.H. Field Cholest-5-ene-3β, 26-diol: synthesis and biomedical use of a deuterated compound Biom Mass Spectrom 9 1982 61 63
    • (1982) Biom Mass Spectrom , vol.9 , pp. 61-63
    • Javitt, N.B.1    Kok, E.2    Lloyd, J.3    Benscath, A.4    Field, F.H.5
  • 15
    • 0036890428 scopus 로고    scopus 로고
    • Synthesis of (25R)-26-hydroxycholesterol
    • J.R. Williams, D.P. Chai, and D. Wright Synthesis of (25R)-26- hydroxycholesterol Steroids 67 2002 1041 1044
    • (2002) Steroids , vol.67 , pp. 1041-1044
    • Williams, J.R.1    Chai, D.P.2    Wright, D.3
  • 16
    • 0002714675 scopus 로고
    • Rapid chromatographic technique for preparative separations with moderate resolution
    • W.C. Still, M. Kahn, and A. Mitra Rapid chromatographic technique for preparative separations with moderate resolution J Org Chem 43 1978 2923 2925
    • (1978) J Org Chem , vol.43 , pp. 2923-2925
    • Still, W.C.1    Kahn, M.2    Mitra, A.3
  • 17
    • 33845379699 scopus 로고
    • 1H NMR spectra by selective excitation of experimental subspectra
    • 1H NMR spectra by selective excitation of experimental subspectra J Am Chem Soc 107 1985 7197 7198
    • (1985) J Am Chem Soc , vol.107 , pp. 7197-7198
    • Dgd, D.1    Bax, A.2
  • 18
    • 0015271658 scopus 로고
    • Experiments on the synthesis of tetracycline. Part XI. Oxidation of ketone acetals and ethers by hydride transfer
    • Barton DHR, P.D. Magnus, G. Smith, G. Streckert, and D. Zurr Experiments on the synthesis of tetracycline. Part XI. Oxidation of ketone acetals and ethers by hydride transfer JCS Perkin I 1971 542 552
    • (1971) JCS Perkin I , pp. 542-552
    • Dhr, B.1    Magnus, P.D.2    Smith, G.3    Streckert, G.4    Zurr, D.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.