Synthesis of biological precursors of cholic acid
This paper describes a new and convenient procedure for the synthesis of 5β-cholestane-3α,7α,12α,24-tetrol(24R and 24 S) and 5β-cholestane-3α, 7α, 12α, 26-tetrol starting from 5β-cholestane-3α,7α,12α,25-tetrol. Dehydration of the 25-hydroxytetrol with glacial acetic acid and acetic anhydride yielded...
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| Format: |
E-Artikel |
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| Sprache: |
Englisch |
| Erschienen: |
1978 |
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| Reproduktion: |
Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 |
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| Übergeordnetes Werk: |
in: Steroids - Amsterdam : Elsevier, 32(1978), 3, Seite 337-344 |
| Übergeordnetes Werk: |
volume:32 ; year:1978 ; number:3 ; pages:337-344 |
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| 520 | |a This paper describes a new and convenient procedure for the synthesis of 5β-cholestane-3α,7α,12α,24-tetrol(24R and 24 S) and 5β-cholestane-3α, 7α, 12α, 26-tetrol starting from 5β-cholestane-3α,7α,12α,25-tetrol. Dehydration of the 25-hydroxytetrol with glacial acetic acid and acetic anhydride yielded a mixture of 5β-cholest-24-ene-3α,7α,12α-triol and the corresponding Δ^2^5 compound. Hydroboration and oxidation of the mixture of Δ^2^4 and Δ^2^5 unsaturated bile alcohols resulted in the formation of 5β-cholestane-3α,7α,12α,24ξ-tetrol and 5β-cholestane-3α,7α,12α,26-tetrol. In addition, smaller amounts of 5β-cholestane-3α, 7α, 12α, 23ξ-tetrol and 5β-cholestane-3α, 7α, 12α-triol were also obtained.The bile alcohols epimeric at C-24 were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass-spectrometry. Tentative assignments of the 24R and 24S configuration was made on the basis of molecular rotation differences. These compounds will be useful for biological studies of cholic acid biosynthesis. | ||
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(DE-627)NLEJ186574886 (DE-599)GBVNLZ186574886 DE-627 ger DE-627 rakwb eng Synthesis of biological precursors of cholic acid 1978 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier This paper describes a new and convenient procedure for the synthesis of 5β-cholestane-3α,7α,12α,24-tetrol(24R and 24 S) and 5β-cholestane-3α, 7α, 12α, 26-tetrol starting from 5β-cholestane-3α,7α,12α,25-tetrol. Dehydration of the 25-hydroxytetrol with glacial acetic acid and acetic anhydride yielded a mixture of 5β-cholest-24-ene-3α,7α,12α-triol and the corresponding Δ^2^5 compound. Hydroboration and oxidation of the mixture of Δ^2^4 and Δ^2^5 unsaturated bile alcohols resulted in the formation of 5β-cholestane-3α,7α,12α,24ξ-tetrol and 5β-cholestane-3α,7α,12α,26-tetrol. In addition, smaller amounts of 5β-cholestane-3α, 7α, 12α, 23ξ-tetrol and 5β-cholestane-3α, 7α, 12α-triol were also obtained.The bile alcohols epimeric at C-24 were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass-spectrometry. Tentative assignments of the 24R and 24S configuration was made on the basis of molecular rotation differences. These compounds will be useful for biological studies of cholic acid biosynthesis. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Dayal, B. oth Batta, A.K. oth Shefer, S. oth Tint, G.S. oth Salen, G. oth in Steroids Amsterdam : Elsevier 32(1978), 3, Seite 337-344 (DE-627)NLEJ17701184X (DE-600)1498762-4 0039-128X nnns volume:32 year:1978 number:3 pages:337-344 http://linkinghub.elsevier.com/retrieve/pii/0039-128X(78)90085-5 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 32 1978 3 337-344 |
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(DE-627)NLEJ186574886 (DE-599)GBVNLZ186574886 DE-627 ger DE-627 rakwb eng Synthesis of biological precursors of cholic acid 1978 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier This paper describes a new and convenient procedure for the synthesis of 5β-cholestane-3α,7α,12α,24-tetrol(24R and 24 S) and 5β-cholestane-3α, 7α, 12α, 26-tetrol starting from 5β-cholestane-3α,7α,12α,25-tetrol. Dehydration of the 25-hydroxytetrol with glacial acetic acid and acetic anhydride yielded a mixture of 5β-cholest-24-ene-3α,7α,12α-triol and the corresponding Δ^2^5 compound. Hydroboration and oxidation of the mixture of Δ^2^4 and Δ^2^5 unsaturated bile alcohols resulted in the formation of 5β-cholestane-3α,7α,12α,24ξ-tetrol and 5β-cholestane-3α,7α,12α,26-tetrol. In addition, smaller amounts of 5β-cholestane-3α, 7α, 12α, 23ξ-tetrol and 5β-cholestane-3α, 7α, 12α-triol were also obtained.The bile alcohols epimeric at C-24 were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass-spectrometry. Tentative assignments of the 24R and 24S configuration was made on the basis of molecular rotation differences. These compounds will be useful for biological studies of cholic acid biosynthesis. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Dayal, B. oth Batta, A.K. oth Shefer, S. oth Tint, G.S. oth Salen, G. oth in Steroids Amsterdam : Elsevier 32(1978), 3, Seite 337-344 (DE-627)NLEJ17701184X (DE-600)1498762-4 0039-128X nnns volume:32 year:1978 number:3 pages:337-344 http://linkinghub.elsevier.com/retrieve/pii/0039-128X(78)90085-5 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 32 1978 3 337-344 |
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(DE-627)NLEJ186574886 (DE-599)GBVNLZ186574886 DE-627 ger DE-627 rakwb eng Synthesis of biological precursors of cholic acid 1978 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier This paper describes a new and convenient procedure for the synthesis of 5β-cholestane-3α,7α,12α,24-tetrol(24R and 24 S) and 5β-cholestane-3α, 7α, 12α, 26-tetrol starting from 5β-cholestane-3α,7α,12α,25-tetrol. Dehydration of the 25-hydroxytetrol with glacial acetic acid and acetic anhydride yielded a mixture of 5β-cholest-24-ene-3α,7α,12α-triol and the corresponding Δ^2^5 compound. Hydroboration and oxidation of the mixture of Δ^2^4 and Δ^2^5 unsaturated bile alcohols resulted in the formation of 5β-cholestane-3α,7α,12α,24ξ-tetrol and 5β-cholestane-3α,7α,12α,26-tetrol. In addition, smaller amounts of 5β-cholestane-3α, 7α, 12α, 23ξ-tetrol and 5β-cholestane-3α, 7α, 12α-triol were also obtained.The bile alcohols epimeric at C-24 were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass-spectrometry. Tentative assignments of the 24R and 24S configuration was made on the basis of molecular rotation differences. These compounds will be useful for biological studies of cholic acid biosynthesis. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Dayal, B. oth Batta, A.K. oth Shefer, S. oth Tint, G.S. oth Salen, G. oth in Steroids Amsterdam : Elsevier 32(1978), 3, Seite 337-344 (DE-627)NLEJ17701184X (DE-600)1498762-4 0039-128X nnns volume:32 year:1978 number:3 pages:337-344 http://linkinghub.elsevier.com/retrieve/pii/0039-128X(78)90085-5 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 32 1978 3 337-344 |
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(DE-627)NLEJ186574886 (DE-599)GBVNLZ186574886 DE-627 ger DE-627 rakwb eng Synthesis of biological precursors of cholic acid 1978 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier This paper describes a new and convenient procedure for the synthesis of 5β-cholestane-3α,7α,12α,24-tetrol(24R and 24 S) and 5β-cholestane-3α, 7α, 12α, 26-tetrol starting from 5β-cholestane-3α,7α,12α,25-tetrol. Dehydration of the 25-hydroxytetrol with glacial acetic acid and acetic anhydride yielded a mixture of 5β-cholest-24-ene-3α,7α,12α-triol and the corresponding Δ^2^5 compound. Hydroboration and oxidation of the mixture of Δ^2^4 and Δ^2^5 unsaturated bile alcohols resulted in the formation of 5β-cholestane-3α,7α,12α,24ξ-tetrol and 5β-cholestane-3α,7α,12α,26-tetrol. In addition, smaller amounts of 5β-cholestane-3α, 7α, 12α, 23ξ-tetrol and 5β-cholestane-3α, 7α, 12α-triol were also obtained.The bile alcohols epimeric at C-24 were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass-spectrometry. Tentative assignments of the 24R and 24S configuration was made on the basis of molecular rotation differences. These compounds will be useful for biological studies of cholic acid biosynthesis. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Dayal, B. oth Batta, A.K. oth Shefer, S. oth Tint, G.S. oth Salen, G. oth in Steroids Amsterdam : Elsevier 32(1978), 3, Seite 337-344 (DE-627)NLEJ17701184X (DE-600)1498762-4 0039-128X nnns volume:32 year:1978 number:3 pages:337-344 http://linkinghub.elsevier.com/retrieve/pii/0039-128X(78)90085-5 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 32 1978 3 337-344 |
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(DE-627)NLEJ186574886 (DE-599)GBVNLZ186574886 DE-627 ger DE-627 rakwb eng Synthesis of biological precursors of cholic acid 1978 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier This paper describes a new and convenient procedure for the synthesis of 5β-cholestane-3α,7α,12α,24-tetrol(24R and 24 S) and 5β-cholestane-3α, 7α, 12α, 26-tetrol starting from 5β-cholestane-3α,7α,12α,25-tetrol. Dehydration of the 25-hydroxytetrol with glacial acetic acid and acetic anhydride yielded a mixture of 5β-cholest-24-ene-3α,7α,12α-triol and the corresponding Δ^2^5 compound. Hydroboration and oxidation of the mixture of Δ^2^4 and Δ^2^5 unsaturated bile alcohols resulted in the formation of 5β-cholestane-3α,7α,12α,24ξ-tetrol and 5β-cholestane-3α,7α,12α,26-tetrol. In addition, smaller amounts of 5β-cholestane-3α, 7α, 12α, 23ξ-tetrol and 5β-cholestane-3α, 7α, 12α-triol were also obtained.The bile alcohols epimeric at C-24 were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass-spectrometry. Tentative assignments of the 24R and 24S configuration was made on the basis of molecular rotation differences. These compounds will be useful for biological studies of cholic acid biosynthesis. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Dayal, B. oth Batta, A.K. oth Shefer, S. oth Tint, G.S. oth Salen, G. oth in Steroids Amsterdam : Elsevier 32(1978), 3, Seite 337-344 (DE-627)NLEJ17701184X (DE-600)1498762-4 0039-128X nnns volume:32 year:1978 number:3 pages:337-344 http://linkinghub.elsevier.com/retrieve/pii/0039-128X(78)90085-5 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 32 1978 3 337-344 |
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This paper describes a new and convenient procedure for the synthesis of 5β-cholestane-3α,7α,12α,24-tetrol(24R and 24 S) and 5β-cholestane-3α, 7α, 12α, 26-tetrol starting from 5β-cholestane-3α,7α,12α,25-tetrol. Dehydration of the 25-hydroxytetrol with glacial acetic acid and acetic anhydride yielded a mixture of 5β-cholest-24-ene-3α,7α,12α-triol and the corresponding Δ^2^5 compound. Hydroboration and oxidation of the mixture of Δ^2^4 and Δ^2^5 unsaturated bile alcohols resulted in the formation of 5β-cholestane-3α,7α,12α,24ξ-tetrol and 5β-cholestane-3α,7α,12α,26-tetrol. In addition, smaller amounts of 5β-cholestane-3α, 7α, 12α, 23ξ-tetrol and 5β-cholestane-3α, 7α, 12α-triol were also obtained.The bile alcohols epimeric at C-24 were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass-spectrometry. Tentative assignments of the 24R and 24S configuration was made on the basis of molecular rotation differences. These compounds will be useful for biological studies of cholic acid biosynthesis. |
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This paper describes a new and convenient procedure for the synthesis of 5β-cholestane-3α,7α,12α,24-tetrol(24R and 24 S) and 5β-cholestane-3α, 7α, 12α, 26-tetrol starting from 5β-cholestane-3α,7α,12α,25-tetrol. Dehydration of the 25-hydroxytetrol with glacial acetic acid and acetic anhydride yielded a mixture of 5β-cholest-24-ene-3α,7α,12α-triol and the corresponding Δ^2^5 compound. Hydroboration and oxidation of the mixture of Δ^2^4 and Δ^2^5 unsaturated bile alcohols resulted in the formation of 5β-cholestane-3α,7α,12α,24ξ-tetrol and 5β-cholestane-3α,7α,12α,26-tetrol. In addition, smaller amounts of 5β-cholestane-3α, 7α, 12α, 23ξ-tetrol and 5β-cholestane-3α, 7α, 12α-triol were also obtained.The bile alcohols epimeric at C-24 were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass-spectrometry. Tentative assignments of the 24R and 24S configuration was made on the basis of molecular rotation differences. These compounds will be useful for biological studies of cholic acid biosynthesis. |
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This paper describes a new and convenient procedure for the synthesis of 5β-cholestane-3α,7α,12α,24-tetrol(24R and 24 S) and 5β-cholestane-3α, 7α, 12α, 26-tetrol starting from 5β-cholestane-3α,7α,12α,25-tetrol. Dehydration of the 25-hydroxytetrol with glacial acetic acid and acetic anhydride yielded a mixture of 5β-cholest-24-ene-3α,7α,12α-triol and the corresponding Δ^2^5 compound. Hydroboration and oxidation of the mixture of Δ^2^4 and Δ^2^5 unsaturated bile alcohols resulted in the formation of 5β-cholestane-3α,7α,12α,24ξ-tetrol and 5β-cholestane-3α,7α,12α,26-tetrol. In addition, smaller amounts of 5β-cholestane-3α, 7α, 12α, 23ξ-tetrol and 5β-cholestane-3α, 7α, 12α-triol were also obtained.The bile alcohols epimeric at C-24 were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass-spectrometry. Tentative assignments of the 24R and 24S configuration was made on the basis of molecular rotation differences. These compounds will be useful for biological studies of cholic acid biosynthesis. |
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<?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01000caa a22002652 4500</leader><controlfield tag="001">NLEJ186574886</controlfield><controlfield tag="003">DE-627</controlfield><controlfield tag="005">20210707052015.0</controlfield><controlfield tag="007">cr uuu---uuuuu</controlfield><controlfield tag="008">070506s1978 xx |||||o 00| ||eng c</controlfield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-627)NLEJ186574886</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)GBVNLZ186574886</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-627</subfield><subfield code="b">ger</subfield><subfield code="c">DE-627</subfield><subfield code="e">rakwb</subfield></datafield><datafield tag="041" ind1=" " ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Synthesis of biological precursors of cholic acid</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="c">1978</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zzz</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">z</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="a">nicht spezifiziert</subfield><subfield code="b">zu</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="520" ind1=" " ind2=" "><subfield code="a">This paper describes a new and convenient procedure for the synthesis of 5β-cholestane-3α,7α,12α,24-tetrol(24R and 24 S) and 5β-cholestane-3α, 7α, 12α, 26-tetrol starting from 5β-cholestane-3α,7α,12α,25-tetrol. Dehydration of the 25-hydroxytetrol with glacial acetic acid and acetic anhydride yielded a mixture of 5β-cholest-24-ene-3α,7α,12α-triol and the corresponding Δ^2^5 compound. Hydroboration and oxidation of the mixture of Δ^2^4 and Δ^2^5 unsaturated bile alcohols resulted in the formation of 5β-cholestane-3α,7α,12α,24ξ-tetrol and 5β-cholestane-3α,7α,12α,26-tetrol. In addition, smaller amounts of 5β-cholestane-3α, 7α, 12α, 23ξ-tetrol and 5β-cholestane-3α, 7α, 12α-triol were also obtained.The bile alcohols epimeric at C-24 were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass-spectrometry. Tentative assignments of the 24R and 24S configuration was made on the basis of molecular rotation differences. These compounds will be useful for biological studies of cholic acid biosynthesis.</subfield></datafield><datafield tag="533" ind1=" " ind2=" "><subfield code="f">Elsevier Journal Backfiles on ScienceDirect 1907 - 2002</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Dayal, B.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Batta, A.K.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Shefer, S.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Tint, G.S.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Salen, G.</subfield><subfield code="4">oth</subfield></datafield><datafield tag="773" ind1="0" ind2="8"><subfield code="i">in</subfield><subfield code="t">Steroids</subfield><subfield code="d">Amsterdam : Elsevier</subfield><subfield code="g">32(1978), 3, Seite 337-344</subfield><subfield code="w">(DE-627)NLEJ17701184X</subfield><subfield code="w">(DE-600)1498762-4</subfield><subfield code="x">0039-128X</subfield><subfield code="7">nnns</subfield></datafield><datafield tag="773" ind1="1" ind2="8"><subfield code="g">volume:32</subfield><subfield code="g">year:1978</subfield><subfield code="g">number:3</subfield><subfield code="g">pages:337-344</subfield></datafield><datafield tag="856" ind1="4" ind2="0"><subfield code="u">http://linkinghub.elsevier.com/retrieve/pii/0039-128X(78)90085-5</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_USEFLAG_H</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">ZDB-1-SDJ</subfield></datafield><datafield tag="912" ind1=" " ind2=" "><subfield code="a">GBV_NL_ARTICLE</subfield></datafield><datafield tag="951" ind1=" " ind2=" "><subfield code="a">AR</subfield></datafield><datafield tag="952" ind1=" " ind2=" "><subfield code="d">32</subfield><subfield code="j">1978</subfield><subfield code="e">3</subfield><subfield code="h">337-344</subfield></datafield></record></collection>
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