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6-methyleneandrosta-1,4-dien-3-one 17β-acetate
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 20℃; Inert atmosphere; | 95% |
With methanol; sodium hydroxide for 2h; Product distribution / selectivity; |
17β-hydroxy-6-methyleneandrosta-4-ene-3-one
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
With N,O-Bis(trimethylsilyl)trifluoroacetamide; chloranil; trifluorormethanesulfonic acid In toluene at 108 - 110℃; for 4h; Product distribution / selectivity; Heating / reflux; | 68.4% |
With trifluorormethanesulfonic acid; N,O-Bis(trimethylsilyl)trifluoroacetamide; chloranil In toluene Inert atmosphere; Reflux; | 68% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone; benzoic acid In benzene at 80 - 82℃; for 5h; Product distribution / selectivity; Heating / reflux; | 14% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane; ethyl acetate |
exemestane
B
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate; acetic acid; trifluoroacetic acid In dichloromethane; acetonitrile at 20℃; for 11h; Inert atmosphere; | A 11.3 mg B 39% |
formaldehyd
1-dehydrotestosterone
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
With N,N-dimethylammonium chloride 1.) isoamyl alcohol, reflux, 2 h, 2.) isoamyl alcohol, reflux, 15 h; Multistep reaction; |
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
exemestane
Conditions | Yield |
---|---|
With Jones reagent In acetone at -20℃; Jones oxidation; Inert atmosphere; | 100% |
With jones reagent In acetone at -20℃; for 0.25h; | 85% |
With Jones reagent In acetone at 0℃; Product distribution / selectivity; |
L-Cysteine
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 20℃; for 24h; Inert atmosphere; | 13% |
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 48h; Ambient temperature; Yield given; |
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature 2: 35 percent / 20percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature View Scheme |
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 85 percent / Jones reagent / acetone / 0.25 h / -20 °C 2: 80 percent / 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature 3: 38 percent / 20percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature View Scheme |
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature 2: 45 percent / 20percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature View Scheme |
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
FCE27353
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / Jones reagent / acetone / 0.25 h / -20 °C 2: 80 percent / 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature View Scheme |
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 85 percent / Jones reagent / acetone / 0.25 h / -20 °C 2: 80 percent / 50percent m-chloroperbenzoic acid / CH2Cl2 / 48 h / Ambient temperature 3: 42 percent / 20percent aq. HClO4 / tetrahydrofuran / 3 h / Ambient temperature View Scheme |
propionyl chloride
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
6-methylenandrosta-1,4-diene-17β-ol-3-one-17-propionate
Conditions | Yield |
---|---|
In pyridine |
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
6-methylenandrosta-1,4-diene-17β-ol-3-one-17-sulphate
Conditions | Yield |
---|---|
With chlorosulfonic acid; dmap In pyridine |
Conditions | Yield |
---|---|
Stage #1: 17β-hydroxy-6-methylen- androsta-1,4-dien-3-one With human liver cytosol; potassium phosphate at 37℃; for 0.05h; pH=7.4; Enzymatic reaction; Stage #2: GLUTATHIONE at 37℃; for 2h; |
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium phosphate; human liver cytosol / 0.05 h / 37 °C / pH 7.4 / Enzymatic reaction 1.2: 2 h / 37 °C 2.1: potassium phosphate; D,L-dithiothreitol; glutamyl transpeptidase; glycylglycine / 37 °C / pH 7.4 / Enzymatic reaction View Scheme |
17β-hydroxy-6-methylen- androsta-1,4-dien-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: potassium phosphate; human liver cytosol / 0.05 h / 37 °C / pH 7.4 / Enzymatic reaction 1.2: 2 h / 37 °C 2.1: potassium phosphate; D,L-dithiothreitol; glutamyl transpeptidase; glycylglycine / 37 °C / pH 7.4 / Enzymatic reaction 3.1: potassium phosphate; manganese(ll) chloride; D,L-dithiothreitol; human liver cytosol / 37 °C / pH 7.4 / Enzymatic reaction View Scheme |
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