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CAS No.: | 516-41-6 |
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Name: | 11-BETA,17-ALPHA,21-TRIHYDROXY-5-ALPHA-PREGNANE-3,20-DIONE |
Article Data: | 7 |
Molecular Structure: | |
Formula: | C21H32O5 |
Molecular Weight: | 364.482 |
Synonyms: | 5-dihydrocortisol;11-BETA,17-ALPHA,21-TRIHYDROXY-5-ALPHA-PREGNANE-3,20-DIONE;5-ALPHA-DIHYDROCORTISOL;5-ALPHA-PREGNAN-11-BETA, 17,21-TRIOL-3,20-DIONE;5ALPHA-PREGNAN-11BETA,17ALPHA,21-TRIOL-3,20-DIONE;ALLODIHYDROCORTISOL;5A-pregnane-11B,17A,21-triol-3,20-*dione |
Density: | 1.249g/cm3 |
Melting Point: | 234-240° |
Boiling Point: | 544.5°Cat760mmHg |
Flash Point: | 297.1°C |
PSA: | 94.83000 |
LogP: | 1.86150 |
Conditions | Yield |
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With sodium methylate In methanol at 20℃; for 1h; | 89% |
With sodium hydroxide In methanol | |
With potassium hydroxide In tetrahydrofuran at 27℃; for 1.5h; |
HYDROCORTISONE
A
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
B
5β-pregnane-11β,17α,21-triol-3,20-dione
Conditions | Yield |
---|---|
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 5%-palladium/activated carbon In ethanol at 80℃; for 6h; | A n/a B 86% |
With 3-Methylpyridine; 5%-palladium/activated carbon; hydrogen at 25℃; for 24h; Reagent/catalyst; Overall yield = 97 %; stereoselective reaction; | A n/a B n/a |
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
tert-butyldimethylsilyl chloride
21-tert-butyldimethylsilyloxy-11β,17α-dihydroxy-5α-pregnane-3,20-dione
Conditions | Yield |
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With pyridine; 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 5h; | 100% |
3,4-dihydro-2H-pyran
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
5α-dihydrocortisol 21-tetrahydropyranyl ether
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane for 2h; Ambient temperature; | 76% |
formaldehyd
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
A
17,20,20,21-bismethylenedioxy-11β-hydroxy-5α-pregnan-3-one
B
11-methoxymethoxy-17,20;20,21-bis-methylenedioxy-pregnan-3-one
Conditions | Yield |
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With hydrogenchloride; chloroform (20Ξ)-11β-methoxymethoxy-17,20;20,21-bis-methylenedioxy-5α-pregnan-3-one; |
Conditions | Yield |
---|---|
Acetylierung; |
formaldehyd
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
A
17,20,20,21-bismethylenedioxy-11β-hydroxy-5α-pregnan-3-one
Conditions | Yield |
---|---|
With hydrogenchloride; chloroform |
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
3α-acetoxy-11β,17α,21-trihydroxy-5α-pregnan-20-one
Conditions | Yield |
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Multi-step reaction with 4 steps 1: 76 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature 2: 72 percent / K-selectride (potassium tri-sec-butylborohydride) / tetrahydrofuran / 1 h / -78 °C 3: 85 percent / pyridine / Ambient temperature 4: 70 percent / 60percent AcOH / 48 h / 37 °C View Scheme |
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
2-oxa-2-((3R,5S,8S,9S,10S,11S,13S,14S,17R)-3,11,17-trihydroxy-10,13-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethyl acetate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 76 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature 2: 72 percent / K-selectride (potassium tri-sec-butylborohydride) / tetrahydrofuran / 1 h / -78 °C 3: imidazole / dimethylformamide; pyridine / 4 h / Ambient temperature 4: 66 percent / 90percent AcOH / 4 h / Ambient temperature 5: 81 percent / pyridine / Ambient temperature 6: 99 percent / 47percent HF / acetonitrile / 0.33 h / Ambient temperature View Scheme |
11β,17α,21-trihydroxy-5α-pregnane-3,20-dione
allotetrahydrocortisol 21-tetrahydropyranyl ether
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 76 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 2 h / Ambient temperature 2: 72 percent / K-selectride (potassium tri-sec-butylborohydride) / tetrahydrofuran / 1 h / -78 °C View Scheme |