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3-Aethylendioxy-1-methylen-5α-androstanol-(17β)
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
(i) Zn-Cu, I2, CH2I2, Et2O, (ii) aq. H2SO4, MeOH; Multistep reaction; |
A
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
F
1-methyl-5α-androst-1-ene-3,17-dione
Conditions | Yield |
---|---|
With Aspergillus niger In methanol at 26℃; for 288h; Microbiological reaction; |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
With Cunninghamella blakesleeana In methanol at 26℃; for 288h; Microbiological reaction; |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
tert-butyldimethylsilyl chloride
17β-(tert.-butyldimethylsilyloxy)-1-methyl-5α-androsta-1-en-3-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 24h; Ambient temperature; | 96% |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
atamestane
Conditions | Yield |
---|---|
With diphenyl diselenide; iodosylbenzene In toluene at 80℃; for 9h; | 51% |
Conditions | Yield |
---|---|
With liver microsomes from Aroclor 1254-induced male Wistar rat In methanol; phosphate buffer at 37℃; pH=7.4; | A 24% B 28% |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
A
1β-Methyl-4,5α-dihydro-testosteron (17β-Hydroxy-1β-methyl-5α-androstan-3-on)
B
mesterolone
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile); tributylzinc hydride In tetrahydrofuran for 1h; Heating; Yield given. Yields of byproduct given; |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
(1S,5R,8R,9S,10S,13S,14S,17S)-1,10,13-Trimethyl-17-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Tributylzinnhydrid, Azobisisobutyronitril / tetrahydrofuran / 1 h / Heating 2: hexamethyldisilazane / pyridine / 0.25 h View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
(1S,5S,8R,9S,10S,13S,14S,17S)-1,10,13-Trimethyl-17-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Tributylzinnhydrid, Azobisisobutyronitril / tetrahydrofuran / 1 h / Heating 2: hexamethyldisilazane / pyridine / 0.25 h View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
1,4-dimethylandrosta-1,4-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 31 percent / iodoxybenzene, diphenyl diselenide / toluene / 7 h / 80 °C 6: 92 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature 7: 83 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-hydroxy-1,4α-dimethyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
1,4α-dimethyl-5α-androst-1-en-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 84 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-hydroxy-1,2,4α-trimethyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature; 2 View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-hydroxy-1,4-dimethylandrosta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 31 percent / iodoxybenzene, diphenyl diselenide / toluene / 7 h / 80 °C 6: 92 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
1,2,4α-trimethyl-5α-androst-1-en-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature; 2 8: 83 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-hydroxy-1,2,4-trimethylandrosta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 33 percent / iodoxybenzene, diphenyl diselenide / toluene / 80 °C 8: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
1,2,4-trimethylandrosta-1,4-dien-3,17-dione
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 33 percent / iodoxybenzene, diphenyl diselenide / toluene / 80 °C 8: 90 percent / 3 percent potassium hydroxide / methanol / 4 h / Ambient temperature 9: 82 percent / chromium trioxide, conc. sulfuric acid / H2O; acetone / 0.25 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-acetyloxy-1,4α-dimethyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-acetyloxy-1,2,4α-trimethyl-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-acetyloxy-1,4-dimethylandrosta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 31 percent / iodoxybenzene, diphenyl diselenide / toluene / 7 h / 80 °C View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-acetyloxy-1,2,4-trimethylandrosta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C 6: 70 percent / Raney nickel / acetone / 0.25 h / Heating 7: 33 percent / iodoxybenzene, diphenyl diselenide / toluene / 80 °C View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-(tert.-butyldimethylsilyloxy)-1,4α-dimethyl-5α-androsta-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min View Scheme |
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
17β-acetyloxy-1,4α-dimethyl-2-<(phenylthio)methyl>-5α-androst-1-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 96 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 1.) lithium diisopropylamide / 1.) THF, 0 deg, 15 min; 2.) THF, -78 deg C, 3 h; 3.) THF, -78 deg C, 15 min; 4.) r.t., 30 min 3: 87 percent / acetic acid / tetrahydrofuran; H2O / 72 h / 50 - 60 °C 4: 95 percent / dimethylaminopyridine / pyridine / 4 h / Ambient temperature 5: 42 percent / various solvent(s); H2O; ethanol / 80 h / 110 °C View Scheme |
N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide
17β-hydroxy-1-methyl-5α-androst-1-en-3-one
C26H46O2Si2
Conditions | Yield |
---|---|
With ammonium iodide; 2-hydroxyethanethiol at 60℃; for 0.333333h; | |
With ammonium iodide; ethanethiol In acetonitrile at 80℃; for 0.5h; |
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