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CAS No.: | 37927-29-0 |
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Name: | (11beta,17alpha)-11,17-dihydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid |
Article Data: | 16 |
Molecular Structure: | |
Formula: | C20H26 O5 |
Molecular Weight: | 346.423 |
Synonyms: | 11b,17-Dihydroxy-3-oxoandrosta-1,4-diene-17b-carboxylic acid; 11b,17a-Dihydroxyandrosta-1,4-dien-3-one-17b-carboxylic acid; PJ 90;Prednienic acid; D1-Cortienicacid |
Density: | 1.33g/cm3 |
Boiling Point: | 570.7°Cat760mmHg |
Flash Point: | 313°C |
PSA: | 94.83000 |
LogP: | 2.08080 |
prednisolon
(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
Conditions | Yield |
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With periodic acid In tetrahydrofuran; methanol at 20℃; for 2h; | 100% |
With sodium periodate; sulfuric acid In methanol; water at 20℃; for 16h; Inert atmosphere; | 98.8% |
With sodium periodate In methanol; water for 0.5h; Heating; Large scale; | 97% |
(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
Conditions | Yield |
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With hydrogenchloride; chromium chloride; mercaptoacetic acid; zinc In ethanol; water at 10 - 30℃; for 0.5h; Temperature; Inert atmosphere; | 98% |
Loteprednol etabonate
A
(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
Conditions | Yield |
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With heptakis(2,6-di-O-methyl)cyclomaltoheptaose; water at 37℃; Kinetics; Activation energy; Further Variations:; Temperatures; Reagents; Solvents; Hydrolysis; |
11α-hydroxy-androsta-1,4-diene-3,17-dione
(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
Conditions | Yield |
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Multi-step reaction with 6 steps 1.1: acetic anhydride; phosphoric acid / dichloromethane / 5 h / 0 - 5 °C / Inert atmosphere 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 1 h / 50 - 60 °C / Inert atmosphere 2.2: 1 h / -5 - 5 °C / Inert atmosphere 3.1: sodium hydrogencarbonate; potassium fluoride / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 3.2: 5 h / 25 °C / Inert atmosphere 4.1: chromium(VI) oxide; sulfuric acid / acetone; water / 0 - 25 °C 5.1: perchloric acid; N-bromoacetamide / acetone / 3.33 h / -5 - 5 °C / Inert atmosphere 6.1: mercaptoacetic acid; chromium chloride; zinc; hydrogenchloride / water; ethanol / 0.5 h / 10 - 30 °C / Inert atmosphere View Scheme |
androsta-1,4,9(11)-triene-3,17-dione
(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: magnesium; ethylene dibromide / tetrahydrofuran / 1 h / 50 - 60 °C / Inert atmosphere 1.2: 1 h / -5 - 5 °C / Inert atmosphere 2.1: sodium hydrogencarbonate; potassium fluoride / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 2.2: 5 h / 25 °C / Inert atmosphere 3.1: chromium(VI) oxide; sulfuric acid / acetone; water / 0 - 25 °C 4.1: perchloric acid; N-bromoacetamide / acetone / 3.33 h / -5 - 5 °C / Inert atmosphere 5.1: mercaptoacetic acid; chromium chloride; zinc; hydrogenchloride / water; ethanol / 0.5 h / 10 - 30 °C / Inert atmosphere View Scheme |
(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hydrogencarbonate; potassium fluoride / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 1.2: 5 h / 25 °C / Inert atmosphere 2.1: chromium(VI) oxide; sulfuric acid / acetone; water / 0 - 25 °C 3.1: perchloric acid; N-bromoacetamide / acetone / 3.33 h / -5 - 5 °C / Inert atmosphere 4.1: mercaptoacetic acid; chromium chloride; zinc; hydrogenchloride / water; ethanol / 0.5 h / 10 - 30 °C / Inert atmosphere View Scheme |
(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: chromium(VI) oxide; sulfuric acid / acetone; water / 0 - 25 °C 2: perchloric acid; N-bromoacetamide / acetone / 3.33 h / -5 - 5 °C / Inert atmosphere 3: mercaptoacetic acid; chromium chloride; zinc; hydrogenchloride / water; ethanol / 0.5 h / 10 - 30 °C / Inert atmosphere View Scheme |
chloro-methylsulfanyl-methane
(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
Conditions | Yield |
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With triethylamine | 98% |
(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
chloroformic acid ethyl ester
Conditions | Yield |
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With triethylamine In dichloromethane at 0 - 10℃; for 0.5h; Large scale; | 96% |
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate In dichloromethane at 20℃; for 3h; Time; | 90.2% |
dichloroacethyl chloride
(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0 02,7. 011,15]heptadeca-3,6-diene-14-carboxylic acid
tetra(n-butyl)ammonium hydrogensulfate
17α-dichloroacetoxy-11β-hydroxyandrosta-1,4-diene-3-one-17β-carboxylic acid
Conditions | Yield |
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With sodium hydrogencarbonate In methanol; dichloromethane; water | 95% |
With sodium hydrogencarbonate In methanol; dichloromethane; water | 95% |
With sodium hydrogencarbonate In dichloromethane; water | |
With sodium hydrogencarbonate In dichloromethane; water |