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Methyl steroids. Studies on the synthesis of 4-methyl- and 4,4-dimethyl-25-hydroxycholestan-3-one derivatives
Iwona Skiera, Zdzisław Paryzek
Language English Country Czech Republic
NLK
ProQuest Central
from 2005-01-01 to 2011
- MeSH
- Alkylation MeSH
- Cholestanes chemical synthesis MeSH
- Hydroxysteroids chemical synthesis MeSH
- Methylation MeSH
- Steroids, Brominated chemical synthesis MeSH
The synthetic routes to 25-hydroxy derivatives of 4-methylcholest-4-ene and 4,4-dimethylcholest-5-ene from methyl lithocholate and methyl 3b-acetoxy-24-homochol-5-en-25-oate (6) have been investigated. The cholest-5-ene-3b,25-diol (7), readily available from 6, was transformed in a few steps into the title compounds. It was also found that bromination of 24-acetoxy-5b-cholan-3-one (1) and of its enol acetate followed by dehydrobromination is not a regioselective reaction. Formation of mixtures of 2b-bromo-3-oxo and 4b-bromo-3-oxo compounds, which gave mixtures of 24-acetoxychol-4-en-3-one (4) and 24-acetoxy-5b-chol-1-en-3-one (5) of similar polarity was observed. 4-Methyl-25-hydroxycholest-4-en-3-one (14) and 4-methyl-25-hydroxycholesta-1,4-dien-3-one (16) are potential substrates for the preparation of 4-methyl analogs of vitamin D3.
Lit.: 33
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- 02285naa 2200361 a 4500
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- CZ-PrNML
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- 20111210121245.0
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- 080122s2007 xr e eng||
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- 024 7_
- $2 doi $a 10.1135/cccc20071319
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- 041 0_
- $a eng
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- $a xr
- 100 1_
- $a Skiera, Iwona
- 245 10
- $a Methyl steroids. Studies on the synthesis of 4-methyl- and 4,4-dimethyl-25-hydroxycholestan-3-one derivatives / $c Iwona Skiera, Zdzisław Paryzek
- 314 __
- $a Faculty of Chemistry, A. Mickiewicz University, Poznan
- 504 __
- $a Lit.: 33
- 520 9_
- $a The synthetic routes to 25-hydroxy derivatives of 4-methylcholest-4-ene and 4,4-dimethylcholest-5-ene from methyl lithocholate and methyl 3b-acetoxy-24-homochol-5-en-25-oate (6) have been investigated. The cholest-5-ene-3b,25-diol (7), readily available from 6, was transformed in a few steps into the title compounds. It was also found that bromination of 24-acetoxy-5b-cholan-3-one (1) and of its enol acetate followed by dehydrobromination is not a regioselective reaction. Formation of mixtures of 2b-bromo-3-oxo and 4b-bromo-3-oxo compounds, which gave mixtures of 24-acetoxychol-4-en-3-one (4) and 24-acetoxy-5b-chol-1-en-3-one (5) of similar polarity was observed. 4-Methyl-25-hydroxycholest-4-en-3-one (14) and 4-methyl-25-hydroxycholesta-1,4-dien-3-one (16) are potential substrates for the preparation of 4-methyl analogs of vitamin D3.
- 650 _2
- $a hydroxysteroidy $x chemická syntéza $7 D006914
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- $a cholestany $x chemická syntéza $7 D002776
- 650 _2
- $a metylace $7 D008745
- 650 _2
- $a alkylace $7 D000478
- 650 _2
- $a steroidy bromované $x chemická syntéza $7 D013257
- 700 1_
- $a Paryzek, Zdzisław
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- $w MED00010973 $t Collection of Czechoslovak chemical communications $g Roč. 72, č. 10 (2007), s. 1319-1330 $x 0010-0765
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- $a 3
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- $a 2007 $b 72 $c 10 $d 1319-1330 $i 0010-0765 $m Collection of Czechoslovak Chemical Communications $x MED00010973
- LZP __
- $a 2007-18/mkmv
