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Derivatives of 16alpha-hydroxy-dehydroepiandrosterone with an additional 7-oxo or 7-hydroxy substituent: synthesis and gas chromatography/mass spectrometry analysis
Pouzar V., Cerný I., Hill M., Bicíková M., Hampl R.
Jazyk angličtina Země Spojené státy americké
- MeSH
- borohydridy MeSH
- cer MeSH
- chloridy MeSH
- dehydroepiandrosteron analogy a deriváty analýza chemie MeSH
- financování organizované MeSH
- hydroxylace MeSH
- indikátory a reagencie MeSH
- magnetická rezonanční spektroskopie MeSH
- molekulární struktura MeSH
- oxidace-redukce MeSH
- plynová chromatografie s hmotnostně spektrometrickou detekcí MeSH
Derivatives of 16alpha-hydroxy-dehydroepiandrosterone, which have an additional oxygen substituent at position 7 (oxo or hydroxy group), were synthesized. Firstly, 17,17-dimethoxyandrost-5-ene-3beta,16alpha-diyl diacetate was prepared and then oxidized with a complex of chromium(VI) oxide and 2,5-dimethylpyrazole to the respective 7-oxo derivative. This key intermediate was both deprotected or reduced by l-Selectride or sodium borohydride in the presence of cerium(III) chloride and then deprotected to give 7-oxo, 7alpha-hydroxy and 7beta-hydroxy derivatives of 16alpha-hydroxy-dehydroepiandrosterone. The target compounds were characterized by (1)H and (13)C NMR spectra and in the form of O-methyloxime-trimethylsilyl derivatives, by gas chromatography/mass spectrometry methods.
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- $a Pouzar, Vladimír, $d 1951-2013 $7 jn20010310027
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- $a Derivatives of 16alpha-hydroxy-dehydroepiandrosterone with an additional 7-oxo or 7-hydroxy substituent: synthesis and gas chromatography/mass spectrometry analysis / $c Pouzar V., Cerný I., Hill M., Bicíková M., Hampl R.
- 314 __
- $a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic.
- 520 9_
- $a Derivatives of 16alpha-hydroxy-dehydroepiandrosterone, which have an additional oxygen substituent at position 7 (oxo or hydroxy group), were synthesized. Firstly, 17,17-dimethoxyandrost-5-ene-3beta,16alpha-diyl diacetate was prepared and then oxidized with a complex of chromium(VI) oxide and 2,5-dimethylpyrazole to the respective 7-oxo derivative. This key intermediate was both deprotected or reduced by l-Selectride or sodium borohydride in the presence of cerium(III) chloride and then deprotected to give 7-oxo, 7alpha-hydroxy and 7beta-hydroxy derivatives of 16alpha-hydroxy-dehydroepiandrosterone. The target compounds were characterized by (1)H and (13)C NMR spectra and in the form of O-methyloxime-trimethylsilyl derivatives, by gas chromatography/mass spectrometry methods.
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- $a cer $7 D002563
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- $a chloridy $7 D002712
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- $a financování organizované $7 D005381
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- $a Černý, Ivan, $d 1952- $7 jx20071129059
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- $a Hill, Martin, $d 1962- $7 mzk2005304431
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- $a Bičíková, Marie $7 xx0060369
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- $a Hampl, Richard, $d 1941- $7 jo20000074077
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