1.Product Introduction Main Contents: Deoxycholic Acid Product Specification: 99% HPLC Appearance: white powder Molecular formula and weight: C24H40O4,392.57200 Density: 1.128 g / cm3 Melting point: 171-174 ° C (lit.) Boilin
main contents: Deoxycholic acid product specification: 99% hplc appearance: white powder molecular formula and weight: c24h40o4,392.57200 density: 1.128 g / cm3 melting point: 171-174 ° c (lit.) boiling point: 547.1ºc at 760 mmhg fla
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inquiryItems Standard Result Assay (Ursolic acid) 98%min 98.22% -----------------------------------------------------------------------------------------------------------
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Deoxycholic acid Basic information Product Name: Deoxycholic acid Synonyms: 17-beta-(1-methyl-3-carboxypropyl)-etiocholane-3-alpha,12-alpha-diol;3,12-dihydroxy-(3alpha,5beta,12alpha)-cho
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inquiryAppearance:white powder Storage:R.T Package:25kg/drum Application:It is used in bacteriological and enzymatic studies and for the solubilization of β-adrenergic receptors Transportation:Express/Sea/Air Port:Any port in China
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Deoxycholic acid [83-44-3] Product Name: Deoxycholic acid Synonyms: 3-alpha,12-alpha-dihydroxy-5-beta-cholan-24-oic acid; (3alpha,5beta,12alpha)-3,12-dihydroxycholan-24-oic acid; (3beta,5alpha,12al
methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate
Deoxycholic acid
Conditions | Yield |
---|---|
Stage #1: methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate With water; sodium hydroxide In tetrahydrofuran; methanol at 25 - 35℃; for 4h; Stage #2: With hydrogenchloride In water pH=1 - 2; Product distribution / selectivity; | 99% |
With water; sodium hydroxide In tetrahydrofuran; methanol at 0 - 35℃; for 4h; Reagent/catalyst; Time; Temperature; Concentration; | 99% |
With lithium hydroxide In tetrahydrofuran; methanol; water at 50℃; | 91% |
Stage #1: methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 20h; Stage #2: With hydrogenchloride; water In 2-methyltetrahydrofuran pH=1.7 - 2; Purification / work up; |
Conditions | Yield |
---|---|
Stage #1: methyl deoxycholate With water; lithium hydroxide In tetrahydrofuran at 20℃; Stage #2: With ammonium chloride In tetrahydrofuran; water; ethyl acetate | 94.3% |
With lithium hydroxide In tetrahydrofuran; water at 20℃; | 94.3% |
3α-hydroxy-12-oxo-5β-cholan-24-oic acid methyl ester
Deoxycholic acid
Conditions | Yield |
---|---|
With water; lithium hydroxide In tetrahydrofuran at 20℃; for 3h; | 94.3% |
Conditions | Yield |
---|---|
With water; sodium hydroxide In tetrahydrofuran; methanol at 20 - 30℃; for 24h; | 92% |
With sodium hydroxide In tetrahydrofuran; methanol at 20 - 30℃; for 24h; | 92 g |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; sodium hydrogencarbonate Erhitzen des Reaktionsprodukts mit Hydrazin und Kaliumhydroxid in Triaethylenglykol bis auf 200grad; | |
With potassium chromate; sodium acetate; acetic acid Erhitzen des Reaktionsprodukts mit Hydrazin-hydrat und aethanol. Natriumaethylat auf 200grad; | |
Multi-step reaction with 3 steps 1: sulfuric acid / 5 h / 20 °C 2: sulfuric acid; sodium bromide; sodium bromate / butan-1-ol; dichloromethane; water / 4 h / 7 - 12 °C 3: hydrazine hydrate; potassium hydroxide / ethylene glycol / 9 h / 120 - 170 °C View Scheme |
Deoxycholic acid
Conditions | Yield |
---|---|
With sodium ethanolate; hydrazine hydrate at 200℃; | |
With sodium methylate at 180℃; |
3α-hydroxy-12-oxo-5β-cholan-24-oic acid methyl ester
A
Lagodeoxycholic acid
B
Deoxycholic acid
Conditions | Yield |
---|---|
With sodium hydroxide; nickel Hydrogenation; |
methyl 7-dehydrocholate diacetate (methyl 3α,12α-diacetoxy-7-oxo-5β-cholan-24-oate)
Deoxycholic acid
Conditions | Yield |
---|---|
With acetic anhydride; toluene-4-sulfonic acid Hydrieren des Reaktionsprodukts an Platin in Essigsaeure; |
Deoxycholic acid
Conditions | Yield |
---|---|
With sodium ethanolate; hydrazine |
Desoxycholsaeure-3-β-D-glucoronid
Deoxycholic acid
Conditions | Yield |
---|---|
With glucuronidase for 1h; Kinetics; pH = 6; |
Deoxycholic acid
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; acetone at 37℃; Kinetics; var. temp., solvent; |
A
Deoxycholic acid
Conditions | Yield |
---|---|
In water; ethylene glycol at 25℃; Equilibrium constant; decomplexation; |
A
Deoxycholic acid
Conditions | Yield |
---|---|
In water; ethylene glycol at 25℃; Equilibrium constant; decomplexation; |
12α-acetoxy-3-oxo-choladien-(4,6)-oic acid-(24)
acetic acid
Deoxycholic acid
Conditions | Yield |
---|---|
anschliessende Hydrolyse.Hydrogenation; |
Conditions | Yield |
---|---|
at 90 - 100℃; Hydrogenation; |
methanol
3α-hydroxy-12-oxo-5β-cholan-24-oic acid methyl ester
A
Lagodeoxycholic acid
B
Deoxycholic acid
Conditions | Yield |
---|---|
Behandlung des Reaktionsprodukts mit warmer methanol. Kalilauge.Hydrogenation; |
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; chloylglycine hydrolase; 2-hydroxyethanethiol In phosphate buffer at 20℃; for 0.333333h; pH=8; | A 100 % Chromat. B n/a |
Conditions | Yield |
---|---|
With ethylenediaminetetraacetic acid; chloylglycine hydrolase; 2-hydroxyethanethiol In phosphate buffer at 20℃; for 0.333333h; pH=8; | A n/a B 100 % Chromat. |
Deoxycholic acid
Conditions | Yield |
---|---|
With hydrazine hydrate; potassium hydroxide In diethylene glycol at 125 - 210℃; Wolff-Kishner reduction; |
9-alpha-hydroxyandrost-4-ene-3,17-dione
Deoxycholic acid
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: hydrogen / palladium 10% on activated carbon / N,N-dimethyl-formamide / 3 h / 25 - 35 °C / 3102.97 Torr 2.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 4.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 4.3: Cooling 5.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 6.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 6.2: Cooling 7.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 8.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 9.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 10.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 11.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 11.2: 0 - 5 °C 12.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 12.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 11 steps 1.1: hydrogen / palladium 10% on activated carbon / N,N-dimethyl-formamide / 3 h / 25 - 35 °C / 3102.97 Torr 2.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 4.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 4.3: Cooling 5.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 6.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 6.2: Cooling 7.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 8.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 9.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 10.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 10.2: 0 - 5 °C 11.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 11.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 11 steps 1.1: hydrogen / palladium 10% on activated carbon / N,N-dimethyl-formamide / 3 h / 25 - 35 °C / 3102.97 Torr 2.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 4.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 4.3: Cooling 5.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 6.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 6.2: Cooling 7.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 8.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 8 - 10 h / 0 °C 8.2: 2 h / 50 - 55 °C 8.3: 6 - 8 h / 25 - 30 °C 9.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 10.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 10.2: 0 - 5 °C 11.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 11.2: pH 1 - 2 View Scheme |
C31H50O6
Deoxycholic acid
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 2.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 3.2: 0 - 5 °C 4.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 4.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate; palladium on activated charcoal; tert.-butylhydroperoxide / dichloromethane / 24 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 13 h / 70 °C / 3102.97 Torr 3: water; sodium hydroxide / methanol; tetrahydrofuran / 4 h / 0 - 35 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: potassium carbonate; palladium on activated charcoal; tert.-butylhydroperoxide / dichloromethane / 24 h / 20 °C 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 2.2: 2 h / 25 - 35 °C 3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 5 - 10 °C 4.1: water; sodium hydroxide / methanol; tetrahydrofuran / 4 h / 0 - 35 °C View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate; palladium on activated charcoal; tert.-butylhydroperoxide / dichloromethane / 24 h / 20 °C 2: hydrogen; palladium on activated charcoal / ethyl acetate / 21 h / 45 - 50 °C / 2585.81 Torr 3: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 5 - 10 °C 4: water; sodium hydroxide / methanol; tetrahydrofuran / 4 h / 0 - 35 °C View Scheme | |
Multi-step reaction with 4 steps 1: potassium carbonate; palladium on activated charcoal; tert.-butylhydroperoxide / dichloromethane / 24 h / 20 °C 2: palladium 10% on activated carbon; hydrogen / ethyl acetate / 13 h / 70 °C / 3102.97 Torr 3: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 5 - 10 °C 4: water; sodium hydroxide / methanol; tetrahydrofuran / 4 h / 0 - 35 °C View Scheme |
9α-hydroxy-5β-androstan-3,17-dione
Deoxycholic acid
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 3.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 3.3: Cooling 4.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 5.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 5.2: Cooling 6.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 7.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 8.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 9.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 10.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 10.2: 0 - 5 °C 11.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 11.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 10 steps 1.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 3.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 3.3: Cooling 4.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 5.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 5.2: Cooling 6.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 7.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 8.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 9.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 9.2: 0 - 5 °C 10.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 10.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 10 steps 1.1: sulfuric acid / dichloromethane / 2.15 h / 10 - 35 °C 2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 3.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 3.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 3.3: Cooling 4.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 5.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 5.2: Cooling 6.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 7.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 8 - 10 h / 0 °C 7.2: 2 h / 50 - 55 °C 7.3: 6 - 8 h / 25 - 30 °C 8.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 9.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 9.2: 0 - 5 °C 10.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 10.2: pH 1 - 2 View Scheme |
(5β)-androst-9(11)-ene-3,17-dione
Deoxycholic acid
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 2.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 2.3: Cooling 3.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 4.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 4.2: Cooling 5.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 6.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 7.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 8.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 9.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 9.2: 0 - 5 °C 10.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 10.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 10 steps 1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 2.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 2.3: Cooling 3.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 4.1: ethylaluminum dichloride / dichloromethane; toluene / 0.25 h / 0 °C / Inert atmosphere 4.2: 18.33 h / 0 - 25 °C / Inert atmosphere 4.3: 0 °C 5.1: hydrogen / platinum(IV) oxide / ethyl acetate / 14 - 16 h / 3620.13 Torr 6.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 7.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 8.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 9.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 9.2: 0 - 5 °C 10.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 10.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 9 steps 1.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 2 h / -45 - -40 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 2.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 2.3: Cooling 3.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 4.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 4.2: Cooling 5.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 6.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 7.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 8.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 8.2: 0 - 5 °C 9.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 9.2: pH 1 - 2 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 1.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 1.3: Cooling 2.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 3.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 3.2: Cooling 4.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 5.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 6.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 7.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 8.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 8.2: 0 - 5 °C 9.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 9.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 8 steps 1.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 1.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 1.3: Cooling 2.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 3.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 3.2: Cooling 4.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 5.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 6.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 7.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 7.2: 0 - 5 °C 8.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 8.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 8 steps 1.1: potassium tert-butylate / tetrahydrofuran / 1.33 h / 25 - 35 °C / Inert atmosphere 1.2: 3 - 5 h / 25 - 35 °C / Inert atmosphere 1.3: Cooling 2.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 3.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 3.2: Cooling 4.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 5.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 8 - 10 h / 0 °C 5.2: 2 h / 50 - 55 °C 5.3: 6 - 8 h / 25 - 30 °C 6.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 7.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 7.2: 0 - 5 °C 8.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 8.2: pH 1 - 2 View Scheme |
(Z)-3α-hydroxy-5β-pregna-9(11),17(20)-diene
Deoxycholic acid
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 2.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 2.2: Cooling 3.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 4.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 5.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 6.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 7.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 7.2: 0 - 5 °C 8.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 8.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 7 steps 1.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 2.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 2.2: Cooling 3.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 4.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 5.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 6.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 6.2: 0 - 5 °C 7.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 7.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 7 steps 1.1: triethylamine / dmap / tert-butyl methyl ether / 2 h / 25 - 35 °C / Inert atmosphere 2.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 2.2: Cooling 3.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 4.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 8 - 10 h / 0 °C 4.2: 2 h / 50 - 55 °C 4.3: 6 - 8 h / 25 - 30 °C 5.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 6.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 6.2: 0 - 5 °C 7.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 7.2: pH 1 - 2 View Scheme |
(Z)-3α-acetoxy-5β-pregna-9(11),17(20)-diene
Deoxycholic acid
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 1.2: Cooling 2.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 3.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 4.1: potassium carbonate; hydrogen / palladium on activated charcoal / dichloromethane / 24 h / 20 °C 5.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 6.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 6.2: 0 - 5 °C 7.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 7.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 6 steps 1.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 1.2: Cooling 2.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 3.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 7 h / 0 - 5 °C 4.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 5.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 5.2: 0 - 5 °C 6.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 6.2: pH 1 - 2 View Scheme | |
Multi-step reaction with 6 steps 1.1: ethylaluminum dichloride / dichloromethane; toluene / 20 h / 0 - 35 °C / Inert atmosphere 1.2: Cooling 2.1: hydrogen / palladium on activated charcoal / ethyl acetate / 16 h / 25 - 35 °C / 3620.13 Torr 3.1: tert.-butylhydroperoxide; sodium hypochlorite / ethyl acetate; water / 8 - 10 h / 0 °C 3.2: 2 h / 50 - 55 °C 3.3: 6 - 8 h / 25 - 30 °C 4.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 16 h / 45 - 50 °C / 2585.81 Torr 5.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 5 h / 0 - 10 °C 5.2: 0 - 5 °C 6.1: sodium hydroxide; water / tetrahydrofuran; methanol / 4 h / 25 - 35 °C 6.2: pH 1 - 2 View Scheme |
Conditions | Yield |
---|---|
With sulfuric acid for 4h; Reflux; | 100% |
With sulfuric acid at 20℃; | 100% |
With hydrogenchloride In water for 2h; Molecular sieve; Reflux; | 100% |
N-Methyltaurine
Deoxycholic acid
3α,12α-dihydroxy-5β-cholan-24-oyl-N-methyltaurine
Conditions | Yield |
---|---|
With triethylamine; 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In N,N-dimethyl-formamide at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
In formic acid; benzene | A 99.8% B n/a |
Conditions | Yield |
---|---|
With perchloric acid; acetic anhydride at 55℃; for 1.5h; | 99% |
With acetic anhydride at 55℃; for 1.5h; | 99% |
at 60℃; for 4h; | 98% |
Deoxycholic acid
ethyl acetate
3α-acetyloxy-12α-hydroxy-5β-cholan-24-oic acid
Conditions | Yield |
---|---|
With Candida antarctica lipase B In hexane at 55℃; for 24h; Enzymatic reaction; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
With ammonium chloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 98.5% |
With tributyl-amine; ammonia; chloroformic acid ethyl ester In 1,4-dioxane 10 deg C, 30 min then rt., 2 h; | 78% |
With ammonia at 220℃; |
Conditions | Yield |
---|---|
With chromium(VI) oxide; sulfuric acid; acetone In water at 20℃; | 98% |
With sodium bromate; ammonium cerium (IV) nitrate In water; acetonitrile at 80℃; Green chemistry; | 95% |
With aluminium(III) chloride hexahydrate; potassium peroxymonosulfate In water at 20℃; for 3h; | 91% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h; | 97% |
With potassium carbonate In tetrahydrofuran Microwave irradiation; |
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 3.5h; | 96.1% |
With dmap In dichloromethane at 20℃; for 1h; Inert atmosphere; | 94% |
With dmap; triethylamine Acetylation; | 92% |
Deoxycholic acid
propargyl alcohol
propargyl 3α,12α-dihydroxy-5β-cholan-24-oate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 55 - 60℃; for 7h; | 96% |
With toluene-4-sulfonic acid at 55 - 60℃; for 7h; | 96% |
With toluene-4-sulfonic acid at 55 - 60℃; for 7h; | 96% |
Deoxycholic acid
propargyl bromide
propargyl 3α,12α-dihydroxy-5β-cholan-24-oate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 6h; | 96% |
Stage #1: Deoxycholic acid With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: propargyl bromide In N,N-dimethyl-formamide for 4h; Inert atmosphere; | 95% |
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 18h; | |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; |
Deoxycholic acid
Cyclopropylamine
24-cyclopropyl-3α,12α-dihydroxy-5β-cholanamide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 0 - 20℃; for 48h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
In methanol at 20℃; | 96% |
Deoxycholic acid
benzylamine
(R)-N-benzyl-4-((3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanamide
Conditions | Yield |
---|---|
With 4-(2-(1,3-dioxa-3a1,8,10-triaza-2,3a,14b-triboradibenzo[fg,op]tetracen-2-yl)phenyl)benzo[c]pyrimido[4,5-e][1,2]azaborinin-6(5H)-ol In fluorobenzene at 85℃; for 16h; Molecular sieve; | 95% |
With tributyl-amine; chloroformic acid ethyl ester In 1,4-dioxane 10 deg C, 30 min then rt., 2 h; | 78% |
With ammonium hydroxide; tributyl-amine; chloroformic acid ethyl ester Multistep reaction; |
Deoxycholic acid
Conditions | Yield |
---|---|
With iron(III) chloride; sodium hydroxide In water at 35℃; pH=8; | 95% |
Conditions | Yield |
---|---|
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; sodium hydroxide In water; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol at 20 - 80℃; | 95% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran Reflux; | 94% |
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating; | 88% |
With lithium aluminium tetrahydride In tetrahydrofuran Ambient temperature; | 80% |
1-hydroxy-pyrrolidine-2,5-dione
Deoxycholic acid
3α,12α-dihydroxy-5β-cholan-24-oic acid 2,5-dioxopyrrolidin-1-yl ester
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 15h; | 94% |
With dicyclohexyl-carbodiimide In tetrahydrofuran; acetonitrile at 25℃; | 84% |
With dicyclohexyl-carbodiimide In tetrahydrofuran for 3.5h; | 7.08 g |
Deoxycholic acid
Conditions | Yield |
---|---|
Stage #1: Deoxycholic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-d6-formamide at 0℃; for 0.25h; Stage #2: L-alanine prop-2-ynyl ester hydrochloride In N,N-dimethyl-formamide at 20℃; | 94% |
Deoxycholic acid
Conditions | Yield |
---|---|
Stage #1: Deoxycholic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: C12H13NO2*ClH In N,N-dimethyl-d6-formamide at 20℃; | 94% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 60℃; for 12h; | 93% |
C9H15NO2
Deoxycholic acid
Conditions | Yield |
---|---|
Stage #1: Deoxycholic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: C9H15NO2 In N,N-dimethyl-d6-formamide at 20℃; | 93% |
Deoxycholic acid
3α,12α-dinitrooxycholanic acid
Conditions | Yield |
---|---|
With nitric acid In acetic anhydride at -5℃; for 0.5h; | 92.6% |
With nitric acid; acetic anhydride |
Deoxycholic acid
ethylene diamine mono-p-toluenesulfonic acid salt
Conditions | Yield |
---|---|
at 220 - 225℃; for 0.75h; | 92% |
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; diethyl ether | 92% |
Deoxycholic acid
Propargylamine
N-(prop-2-yn-1-yl)-3α,12α-dihydroxy-5β-cholan-24-amide
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 28℃; for 12h; | 92% |
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; | |
Stage #1: Deoxycholic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.25h; Stage #2: Propargylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 24h; | 3.2 g |
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