17-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one
Stanolone
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 20℃; for 3h; | 97.5% |
(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol
Stanolone
Conditions | Yield |
---|---|
With diiodosilane In chloroform at -42℃; for 0.166667h; | 95% |
(5S,8R,9S,10S,13S,14S,17S)-17-(2-Methoxy-ethoxymethoxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-one
Stanolone
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; sodium iodide In acetonitrile at -20℃; for 0.75h; | 95% |
5α-androstan-17β-ol-3-one tosylhydrazone
Stanolone
Conditions | Yield |
---|---|
With copper(II) sulfate In tetrahydrofuran; methanol; water for 17h; Heating; | 95% |
17β-Hydroxy-5α-androstan-3-one 1,2-Ethanediyl Dithioacetal
Stanolone
Conditions | Yield |
---|---|
With tri(p-bromophenyl)amine; lithium perchlorate; silica gel; sodium hydrogencarbonate In water; acetonitrile for 2h; electrolysis; further reagent: tris(4-bromophenyl)ammoniumyl hexachloroantimonate; | 91% |
With tri(p-bromophenyl)amine; lithium perchlorate In water; acetonitrile Kinetics; Mechanism; cyclovoltammetry; |
(5S,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-17-triethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-3-one
Stanolone
Conditions | Yield |
---|---|
With polymer-bound NMe3(1+)*F(1-) In methanol at 20℃; for 24h; | 90% |
C33H51NO4
Stanolone
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethyl-1,8-diaminonaphthalene In tetrahydrofuran Heating; | 88% |
Stanolone
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 60 - 65℃; Solvent; Reagent/catalyst; | 78% |
Conditions | Yield |
---|---|
With lithium; isopropyl alcohol In tetrahydrofuran; diethyl ether; ammonia at -33℃; for 1.5h; | A n/a B 73% C n/a D n/a |
Stanolone
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; | 71% |
3,17β-bis-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-5α-androst-2-ene
Stanolone
Conditions | Yield |
---|---|
With sodium methylate In N,N-dimethyl-formamide at 60℃; for 1h; | 58% |
Conditions | Yield |
---|---|
biochem. proc. with 5α-reductase of Penicillin decumbens; | A 10% B 40% |
With potato dextrose broth medium In ethanol at 24 - 26℃; for 96h; Penicillium decumbens ATCC 10436; | A 28% B 37% |
Conditions | Yield |
---|---|
With palladium on activated charcoal; hydrogen In tetrahydrofuran at 20℃; for 6h; | A n/a B 39% |
With hydrogen; palladium In pyridine at 25℃; under 760 Torr; Rate constant; selectivity to 5β compound; | |
With hydrogen bromide; hydrogen; palladium In tetrahydrofuran at 25℃; under 760 Torr; Rate constant; selectivity to 5β compound; | |
With 2,2'-azobis(isobutyronitrile); tributylzinc hydride In tetrahydrofuran for 1h; Heating; Yield given. Yields of byproduct given; | |
With hydrogen; palladium on activated charcoal In methanol | A 54 % Chromat. B 42 % Chromat. |
5-androgen-3,17-diol
A
Epiandrosterone
B
Stanolone
C
androstanedione
Conditions | Yield |
---|---|
at 25℃; for 12h; electrolysis: nickel net anode, cylindrical stainless steel cathode; electrolyte: 0.01M KOH/t-butanol - water (1:1); | A 3% B 28% C 30% |
Conditions | Yield |
---|---|
With 5α-reductase from human prostate or liver; NADPH Equilibrium constant; Kinetics; Mechanism; Vmax, Km, var. of conc. of T, NADPH; | |
With 1,4-dioxane; diethyl ether; lithium Reagens 4:fluess.NH3; | |
With glucose-6-phosphate dehydrogenase; α-D-glucose 6-phosphate; NADP; human prostatic 5-α-reductase at 37℃; for 0.5h; Enzyme kinetics; |
Conditions | Yield |
---|---|
With diethyl ether; palladium Hydrogenation; |
Conditions | Yield |
---|---|
With methanol; selenium(IV) oxide anschliessend mit NaBH4 und KOH in H2O und Erwaermen des Reaktionsprodukts in Aceton mit wss.HCl; | |
Yield given. Multistep reaction; | |
Multi-step reaction with 3 steps 1: 83 percent / oxalic acid / Heating 2: NaBH4 / methanol / 1 h / 0 deg C to room temp. 3: 95 percent / diiodosilane / CHCl3 / 0.17 h / -42 °C View Scheme | |
Multi-step reaction with 2 steps 1: benzene; ethanolic HCl / 75 °C 2: sodium; propanol-(1) / und Erwaermen des Reaktionsprodukts mit wss.-aethanol.HCl View Scheme | |
With rabbit 3-hydroxyhexobarbital dehydrogenase (AKR1C29); NADPH In aq. phosphate buffer; ethyl acetate at 37℃; for 0.5h; pH=7.4; Catalytic behavior; Kinetics; Enzymatic reaction; |
Stanolone
Conditions | Yield |
---|---|
With hydrogenchloride |
Stanolone
Conditions | Yield |
---|---|
With propan-1-ol; sodium und Erwaermen des Reaktionsprodukts mit wss.-aethanol.HCl; |
17β-hydroxy-5α-androstan-3-one semicarbazone
Stanolone
Conditions | Yield |
---|---|
With sodium acetate; acetic acid; 2-oxo-propionic acid Regeneration; |
5alpha-Androstane-3beta,17beta-diol-17-hexahydrobenzoate
Stanolone
Conditions | Yield |
---|---|
With copper at 210℃; unter vermindertem Druck; und Erwaermen des Reaktionsprodukts mit methanol.Alkalilauge; | |
With chromium(VI) oxide; acetic acid und Erwaermen des Reaktionsprodukts mit methanol.Alkalilauge; | |
With aluminum tri-tert-butoxide; toluene; p-benzoquinone und Erwaermen des Reaktionsprodukts mit methanol.Alkalilauge; |
testosterone
A
Epiandrosterone
B
Stanolone
C
cis-androsterone
D
androstanedione
E
5-androgen-3,17-diol
F
androstanediol
Conditions | Yield |
---|---|
With total testicular homogenate of adult Sprague-Dawley rats treated with 6, des-Gly-NH210>LHRH ethylamide Product distribution; metabolism, <3H>labelled study, further: equine antibovine LH serum (JOAN-5-31-67); |
testosterone
A
Stanolone
B
Androstenedione
C
androstanedione
D
androstanediol
Conditions | Yield |
---|---|
Product distribution; in vivo metabolism in epididymis of rats, influenced by estradiol-17β or cyproterone acetate, <3H>labeled study; |
testosterone
A
Stanolone
B
cis-androsterone
C
androstanedione
D
5-androgen-3,17-diol
E
androstanediol
Conditions | Yield |
---|---|
With carbon dioxide; 5α-reductase in testicular cells of adult male Sprague-Dawley rats; oxygen; NADP at 37℃; for 1.5h; Product distribution; Kinetics; <3H>labelled, metabolism with or without 7α-hydroxytestosterone; |
testosterone
A
Stanolone
B
5β-androstan-17β-ol-3-one
C
5-androgen-3,17-diol
D
4-androstenediol
E
4-Androstene-3alpha,17beta-diol
Conditions | Yield |
---|---|
With H2SiEt2; Rh-(R,R)-(+)-DIOP for 24h; Product distribution; other reducing agents; |
testosterone
A
Stanolone
B
7α,17β-dihydroxyandrost-4-en-3-one
C
5β-androstanediol
D
5α-androstane-3α/β,17β-diol
Conditions | Yield |
---|---|
With 7α-hydroxylase from microsomes of testicular tissue from Wistar rats injected or not intraperitoneally with human chorionic gonadotrophin till 24 h before kill; Krebs Ringer buffer; NADPH In ethanol at 37℃; for 0.25h; Product distribution; Kinetics; <4-14C>labeled study, Michaelis-Menton const. Km, maximal transformation rate Vm; |
Conditions | Yield |
---|---|
In water at 25℃; for 240h; biotransformation with cultures of Cephalosporium aphidicola (IMI 68689), other androstanones; | 70 mg |
In ethanol; water at 25℃; for 240h; fermentation with cultures of Cephalosporium aphidicola (IMI 68689); Yield given; |
Pregnenolone
A
testosterone
B
Progesterone
C
Stanolone
D
dehydroepiandrosterone
E
Androstenedione
Conditions | Yield |
---|---|
With human LH LER; isolated theca of LAK:LVG (SYR) hamsters at 37℃; for 2h; Product distribution; <3H>labeled, metabolism, var. of conc., time of incubation, preincubation, without LH; | A 0.00094 mg B 0.00006 mg C 0.00017 mg D 0.00026 mg E 0.00030 mg |
Androstenedione
A
estradiol
B
Estrone
C
testosterone
D
Stanolone
E
Etiocholanolone
F
cis-androsterone
Conditions | Yield |
---|---|
With carcinoma; gynecomastia; mammary dysplasia at 37℃; for 1.5h; Product distribution; cofactors under 95percent O2: 5percent CO2, <3H>labeled study; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; divinylbenzene template polymer In tetrahydrofuran Product distribution; Ambient temperature; other steroid ketones; molecular imprinting of solid polymer; |
Stanolone
3-oxo-5α-androstan-17β-ol-3-18O
Conditions | Yield |
---|---|
With hydrogenchloride; 18O-labeled water In 1,4-dioxane at 75℃; for 24h; sealed tube; | 100% |
Stanolone
acryloyl chloride
Acrylic acid (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxo-hexadecahydro-cyclopenta[a]phenanthren-17-yl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 1h; | 100% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; | 100% |
With triethylamine In chloroform at 25℃; for 0.25h; | 90% |
Stanolone
ethane-1,2-dithiol
17β-Hydroxy-5α-androstan-3-one 1,2-Ethanediyl Dithioacetal
Conditions | Yield |
---|---|
With zeolite HSZ-360 In dichloromethane for 15h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With triethylamine; sodium hydroxide In tetrahydrofuran; water at 20 - 60℃; for 5h; | 100% |
Conditions | Yield |
---|---|
With 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate In dichloromethane for 1.5h; Ambient temperature; | 99% |
With dipyridinium dichromate In dichloromethane at 20℃; for 2h; Inert atmosphere; | 99% |
With N-chloro-succinimide; 4 A molecular sieve; potassium carbonate; N-(phenylthio)-N-(tert-butyl)amine In dichloromethane at 20℃; for 1h; | 96% |
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 6h; Inert atmosphere; | 99% |
With pyridine; dmap at 20℃; |
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 2h; Ambient temperature; | 98.3% |
O-(2-hydroxyethyl)hydroxylamine
Stanolone
(Z)-17β-hydroxy-5α-androstan-3-one O-(2-hydroxyethyl)oxime
Conditions | Yield |
---|---|
With pyridine; acetic acid In ethanol for 0.5h; Heating; | 97% |
Stanolone
tert-butyldimethylsilyl chloride
17-((tert-butyldimethylsilyl)oxy)-10,13-dimethylhexadecahydro-3H-cyclopenta[a]phenanthren-3-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature; | 97% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; silylation; | 91% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; | 91% |
Stanolone
methyl 2-((tetrahydro-2H-pyran-2-yl)oxy)acetate
(2α,5α,17β)-17-Hydroxy-2-<<(tetrahydro-2H-pyran-2-yl)oxy>acetyl>androstan-3-one
Conditions | Yield |
---|---|
With hydrogenchloride In N-methyl-acetamide; methanol | 96% |
With sodium hydride 1) DMF, 1 h, rt, 2) DMF, 24 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
In pyridine at 60℃; for 2h; | 96% |
Stanolone
tert-butylchlorodiphenylsilane
Conditions | Yield |
---|---|
With 1H-imidazole; dmap In dichloromethane at 20℃; for 5h; | 96% |
Stanolone
ethylene glycol
(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethylhexadecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 3h; Heating; | 95% |
With toluene-4-sulfonic acid In benzene for 24h; Heating; | 88% |
With pyridine hydrochloride In toluene for 16h; Heating; | 84% |
Stanolone
trisylhydrazine
17β-hydroxy-5α-androstan-3-one 2,4,6-tri-isopropylbenzenesulphonyl hydrazone
Conditions | Yield |
---|---|
In methanol at 20℃; | 94% |
trifluoromethylsulfonic anhydride
Stanolone
17β-triflate-5α-androstan-3-one
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0℃; for 0.25h; Condensation; | 94% |
Stanolone
bis-(2-methyl-1H-imidazol-1-yl)methanone
3-oxo-5α-androst-17β-yl-2'-methyl-1H-imidazole-1-carboxylate
Conditions | Yield |
---|---|
In acetonitrile for 70h; Heating; | 94% |
Stanolone
perfluorotoluene
3,17β-bis-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-5α-androst-2-ene
Conditions | Yield |
---|---|
With cesium fluoride In N,N-dimethyl-formamide for 4h; Heating; | 93% |
Stanolone
methyl chloroformate
17β-methoxycarbonyloxy-5α-androstan-3-one
Conditions | Yield |
---|---|
In pyridine at 0℃; for 24h; | 92% |
Stanolone
2,3-Dipyridin-2-ylquinoxaline-6-carboxylic acid
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h; | 92% |
Stanolone
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 48h; Pictet-Spengler Synthesis; Reflux; Sealed tube; | 92% |
With hydrogenchloride In ethanol for 24h; Sealed tube; Reflux; |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 20℃; for 3h; Temperature; Claisen-Schmidt Condensation; regioselective reaction; | 92% |
Stanolone
(2Z)-2-methyl-2-butenoic 2,4,6-trichlorobenzoic anhydride
Angelate Ester of 5α-androstan-17β-ol-3-one
Conditions | Yield |
---|---|
In toluene at 70℃; for 23h; | 91% |
Stanolone
(5R,8R,9S,10S,13S,14S,17S)-10,13-Dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-ol
Conditions | Yield |
---|---|
With acetic acid; zinc In water at 20℃; for 12h; | 91% |
With zinc In acetic acid at 15℃; for 0.25h; ultrasonic irradiation; | 90% |
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 200 - 220℃; for 16h; | 86% |
With acetic acid; zinc In water at 20℃; for 16h; |
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol at 20℃; for 3h; Claisen-Schmidt Condensation; regioselective reaction; | 91% |
Stanolone
N,N-dimethyl-formamide
3-oxo-5α-androstan-17β-yl formate
Conditions | Yield |
---|---|
With diphenylphosphinopolystyrene; iodine In dichloromethane at 0℃; for 1h; | 90% |
1. | spm-nml-par 12 mg/8W-I | JEZOAO Journal of Experimental Zoology 205 (1978),403. |
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