Our Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con
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inquiryHubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine,Traditional Chinese Medicine)
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inquiryZibo Hangyu Biotechnology Development Co., Ltd is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality pharmaceuticals, intermediates, special chemicals and OLED intermediates and other fine chemi
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inquiryFactory supply high purity low priceAppearance:solid or liquid Storage:sealed in cool and dry place Package:As customer's requested Application:Pharma Intermediate Transportation:by courier/air/sea Port:Any port in China
Oleana-1,9(11)-dien-28-oic acid, 2-cyano-3,12-dioxo-Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:pharmaceutical intermediate Transportation:by air, by sea, by express
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inquiryBOC Sciences provides a wide range of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecule and chiral compounds. Package:
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inquiryChangzhou Extraordinary Pharmatech co., LTD. As a leading chemical manufacturer and supplier in China.DAS authentication is passed.We can provide the popular precursor chemicals, we have our own strong R & D team, have our own laboratories and fa
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PI &PI Biotech Inc. provides great quality of APIs and Drug Impurities. Application:R & D
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inquiryU-CHEMO Holding Co.,Limited is a very fast developing high-technology enterprise combining with manufacture and sales.U-CHEMO supply high quality products and excellent service to our customers.We make the insect pheromones, censor in the quality con
United Scientific Company Located in Shanghai of China , is a competitive player in the global specialty and fine chemical market. Fenghua has both the expertise and flexibility to produce a wide range of chemicals. Focusing on developing the innovat
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inquiryNanjing Chemlin Chemical Industry Co., Ltd was established in Aug,1999, located in the industrial park of Nanjing University of Technology, It is a private enterprises in Jiangsu Province with 1200 square meters’ R&D center. Our R&D center has a well
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inquiry2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid cas: 218600-44-3 Storage:hermetically sealed & avoid heat, moisture and light Application:2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid cas: 218600-44-3 Port:Tianjin
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inquiry1.We have rich experience in the development and production 2.Our factory is in Shanghai of China,We have convenient traffic conditions.3.We have advanced testing equipment and shipping line. Package:5g, 10g, 50g, 100g, 2kg Application:Pharmaceutical
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Shanghai Caerulum Pharma Discovery is the manufacturer of APIs and intermediates of some of the latest compounds in the market. Our focus is on cancer, diabetes and other therapeutic areas. Shanghai Caerulum Pharma Discovery (CPD) offers high qua
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inquirybardoxolone methyl
bardoxolone
Conditions | Yield |
---|---|
With lithium iodide In N,N-dimethyl-formamide | 71% |
With lithium iodide In N,N-dimethyl-formamide | 71% |
With lithium iodide In N,N-dimethyl-formamide at 153℃; for 12h; Inert atmosphere; | 70.3% |
With lithium iodide In N,N-dimethyl-formamide for 4h; Heating; | 68% |
With lithium iodide In N,N-dimethyl-formamide Inert atmosphere; Reflux; | 44% |
tert‐butyl N‐[2‐(N‐hydroxycarbamimidoyl)ethyl]carbamate
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride
B
bardoxolone
Conditions | Yield |
---|---|
Stage #1: tert‐butyl N‐[2‐(N‐hydroxycarbamimidoyl)ethyl]carbamate; 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With tetra(n-butyl)ammonium hydroxide In tetrahydrofuran; water at 20℃; for 5h; Inert atmosphere; | A 45% B n/a |
tert‐butyl N‐[2‐(N‐hydroxycarbamimidoyl)ethyl]carbamate
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride
B
bardoxolone
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; |
3-methoxypropionamidoxime hydrochloride
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride
B
bardoxolone
Conditions | Yield |
---|---|
With triethylamine; trimethylamine In dichloromethane at 20℃; Inert atmosphere; |
methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 97 percent / methanolic KOH / 0.5 h / Heating 2: 92 percent / Jones reagent / acetone / 0.17 h / 20 °C 3: 99 percent / NaOMe / benzene / 2 h / 20 °C 4: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 5: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 6: 92 percent / DDQ / benzene / 0.5 h / Heating 7: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme | |
Multi-step reaction with 7 steps 1: aq. KOH / methanol 2: CrO3, H2SO4 3: 100 percent / sodium methoxide / benzene 4: 61 percent / NH2OH*HCl / aq. ethanol 5: 100 percent / sodium methoxide / methanol; diethyl ether 6: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 7: 71 percent / LiI / dimethylformamide View Scheme | |
Multi-step reaction with 6 steps 1: potassium hydroxide; water / methanol 2: sodium methylate / benzene 3: hydroxylamine hydrochloride / water; ethanol 4: sodium methylate / methanol; diethyl ether 5: Phenylselenyl chloride / ethyl acetate 6: lithium iodide / N,N-dimethyl-formamide View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium hydroxide / methanol / 1 h / Reflux 2.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 3.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 3.2: 0.08 h / -78 - 20 °C 4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 5.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme |
methyl 3,12-dioxoolean-9(11)-en-28-oate
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 99 percent / NaOMe / benzene / 2 h / 20 °C 2: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 3: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 4: 92 percent / DDQ / benzene / 0.5 h / Heating 5: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme | |
Multi-step reaction with 5 steps 1: 100 percent / sodium methoxide / benzene 2: 61 percent / NH2OH*HCl / aq. ethanol 3: 100 percent / sodium methoxide / methanol; diethyl ether 4: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 5: 71 percent / LiI / dimethylformamide View Scheme | |
Multi-step reaction with 5 steps 1: sodium methylate / benzene 2: hydroxylamine hydrochloride / water; ethanol 3: sodium methylate / methanol; diethyl ether 4: Phenylselenyl chloride / ethyl acetate 5: lithium iodide / N,N-dimethyl-formamide View Scheme | |
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 1.2: 0.08 h / -78 - 20 °C 2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 3.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme |
methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 92 percent / Jones reagent / acetone / 0.17 h / 20 °C 2: 99 percent / NaOMe / benzene / 2 h / 20 °C 3: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 4: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 5: 92 percent / DDQ / benzene / 0.5 h / Heating 6: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme | |
Multi-step reaction with 6 steps 1: CrO3, H2SO4 2: 100 percent / sodium methoxide / benzene 3: 61 percent / NH2OH*HCl / aq. ethanol 4: 100 percent / sodium methoxide / methanol; diethyl ether 5: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 6: 71 percent / LiI / dimethylformamide View Scheme | |
Multi-step reaction with 4 steps 1.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 2.2: 0.08 h / -78 - 20 °C 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 4.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme |
methyl 12-oxoisoxazolo[4,5-b]olean-9(11)-en-28-oate
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 2: 92 percent / DDQ / benzene / 0.5 h / Heating 3: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme | |
Multi-step reaction with 3 steps 1: 100 percent / sodium methoxide / methanol; diethyl ether 2: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 3: 71 percent / LiI / dimethylformamide View Scheme | |
Multi-step reaction with 3 steps 1: sodium methylate / methanol; diethyl ether 2: Phenylselenyl chloride / ethyl acetate 3: lithium iodide / N,N-dimethyl-formamide View Scheme |
2-cyano-3-hydroxy-12-oxoolean-2(3),9(11)-dien-28-oic acid
bardoxolone
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.25h; Reflux; | 91% |
methyl 2-hydroxymethylene-3,12-dioxoolean-9(11)-en-28-oate
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 2: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 3: 92 percent / DDQ / benzene / 0.5 h / Heating 4: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme |
1,2-dihydro-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 92 percent / DDQ / benzene / 0.5 h / Heating 2: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme |
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 2: 71 percent / LiI / dimethylformamide View Scheme | |
Multi-step reaction with 2 steps 1: Phenylselenyl chloride / ethyl acetate 2: lithium iodide / N,N-dimethyl-formamide View Scheme | |
Multi-step reaction with 2 steps 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 2: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme |
2-cyano-3-hydroxy-12-oxoolean-2(3),9(11)-dien-28-oic acid
A
2-cyano-3,12-dioxooleana-1,9(11)-diene-13β,28-lactone
B
bardoxolone
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 24h; Reflux; | A 58% B 28% |
(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Formyl-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 61 percent / NH2OH*HCl / aq. ethanol 2: 100 percent / sodium methoxide / methanol; diethyl ether 3: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 4: 71 percent / LiI / dimethylformamide View Scheme | |
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride / water; ethanol 2: sodium methylate / methanol; diethyl ether 3: Phenylselenyl chloride / ethyl acetate 4: lithium iodide / N,N-dimethyl-formamide View Scheme |
Oleanolic acid
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere 2.1: potassium carbonate / acetone / 24 h / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 4.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 5.1: potassium hydroxide / methanol / 1 h / Reflux 6.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 7.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 7.2: 0.08 h / -78 - 20 °C 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 9.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 9 steps 1.1: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere 2.1: potassium carbonate / acetone / 24 h / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C 4.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 5.1: potassium hydroxide / methanol / 1 h / Reflux 6.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 7.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 7.2: 0.08 h / -78 - 20 °C 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 9.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; fluorobenzene / 24 h / 85 °C / Inert atmosphere 3.1: 3-chloro-benzenecarboperoxoic acid; hydrogen bromide / dichloromethane / 26 h / 20 °C 3.2: 24 h / 35 °C 4.1: potassium iodide / N,N-dimethyl-formamide / 30 h / 120 °C 5.1: lithium iodide / N,N-dimethyl-formamide / 12 h / 153 °C / Inert atmosphere View Scheme |
(4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 2.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 3.1: potassium hydroxide / methanol / 1 h / Reflux 4.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 5.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 5.2: 0.08 h / -78 - 20 °C 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 7.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 7 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C 2.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 3.1: potassium hydroxide / methanol / 1 h / Reflux 4.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 5.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 5.2: 0.08 h / -78 - 20 °C 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 7.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme |
oleanolic acid 3-acetate
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: potassium carbonate / acetone / 24 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 3.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 4.1: potassium hydroxide / methanol / 1 h / Reflux 5.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 6.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 6.2: 0.08 h / -78 - 20 °C 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 8.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme | |
Multi-step reaction with 8 steps 1.1: potassium carbonate / acetone / 24 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C 3.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 4.1: potassium hydroxide / methanol / 1 h / Reflux 5.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 6.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 6.2: 0.08 h / -78 - 20 °C 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 8.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme |
methyl 3-O-β-acetyl-11-dehydro-12-oxo-18β-oleanolate
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 2.1: potassium hydroxide / methanol / 1 h / Reflux 3.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 4.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 4.2: 0.08 h / -78 - 20 °C 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 6.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme |
oleanolic acid methyl ester
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; fluorobenzene / 24 h / 85 °C / Inert atmosphere 2.1: 3-chloro-benzenecarboperoxoic acid; hydrogen bromide / dichloromethane / 26 h / 20 °C 2.2: 24 h / 35 °C 3.1: potassium iodide / N,N-dimethyl-formamide / 30 h / 120 °C 4.1: lithium iodide / N,N-dimethyl-formamide / 12 h / 153 °C / Inert atmosphere View Scheme |
(4aS,6aS,6bR,8aR,12aR,12bR,14bS)-methyl2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,12b,13,14b-octadecahydropicene-4a-carboxylate
bardoxolone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 3-chloro-benzenecarboperoxoic acid; hydrogen bromide / dichloromethane / 26 h / 20 °C 1.2: 24 h / 35 °C 2.1: potassium iodide / N,N-dimethyl-formamide / 30 h / 120 °C 3.1: lithium iodide / N,N-dimethyl-formamide / 12 h / 153 °C / Inert atmosphere View Scheme |
bardoxolone
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.333333h; Reflux; |
bardoxolone
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride
Conditions | Yield |
---|---|
With oxalyl dichloride In dichloromethane | 100% |
With oxalyl dichloride In dichloromethane at 20℃; | 100% |
With oxalyl dichloride In dichloromethane | 100% |
bardoxolone
(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicene-4a-carbonyl azide
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; triethylamine at 0 - 20℃; | 90% |
With diphenyl phosphoryl azide; triethylamine In toluene at 20℃; for 6h; | 90% |
bardoxolone
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
Conditions | Yield |
---|---|
With Aliquat 336; potassium carbonate In dichloromethane | 75% |
With potassium carbonate; Aliquat 336 In dichloromethane; water | 75% |
bardoxolone
(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicene-4a-carbonyl fluoride
Conditions | Yield |
---|---|
With diethylamino-sulfur trifluoride In chloroform at 20℃; for 6.5h; | 94% |
bardoxolone
Conditions | Yield |
---|---|
With dihydrogen peroxide In methanol; water; acetonitrile at 20℃; for 30h; | 90% |
Conditions | Yield |
---|---|
Stage #1: bardoxolone With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1.16667h; Cooling with ice; Stage #2: methanol In dichloromethane for 1h; | 96% |
bardoxolone
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 45℃; for 4h; | 68% |
bardoxolone
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 45℃; for 4h; | 74% |
bardoxolone
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran | 84% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating / reflux; | 83% |
Conditions | Yield |
---|---|
Stage #1: isosorbide mononitrate; bardoxolone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: propionyl chloride In N,N-dimethyl-formamide | 35% |
Conditions | Yield |
---|---|
Stage #1: isosorbide mononitrate; bardoxolone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: acetyl chloride In N,N-dimethyl-formamide for 6h; | 35% |
bardoxolone
(4aR,6aS,6bR,8aS,12aS,12bR,14bS)-8a-isocyanato-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-2-carbonitrile
Conditions | Yield |
---|---|
Stage #1: bardoxolone With diphenyl phosphoryl azide; triethylamine In toluene at 0 - 20℃; Stage #2: In benzene at 80℃; for 2h; | |
Multi-step reaction with 2 steps 1: diphenyl phosphoryl azide; triethylamine / 0 - 20 °C 2: benzene / 2 h / 80 °C View Scheme |
bardoxolone
A
(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicene-4a-carbonyl azide
B
(4aR,6aS,6bR,8aS,12aS,12bR,14bS)-8a-isocyanato-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-2-carbonitrile
Conditions | Yield |
---|---|
With diphenyl phosphoryl azide; triethylamine In toluene at 0 - 20℃; Overall yield = 94 %; Overall yield = 19.7 g; |
bardoxolone
N-(2-(2-(2-(2-amidoethoxy)ethoxy)ethoxy)ethoxy)biotinamide
Conditions | Yield |
---|---|
With 2`,3`-dideoxycytidine; dmap In dichloromethane at 20℃; for 48h; | 79% |
bardoxolone
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride
2-cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; for 1.5h; | 96% |
bardoxolone
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating; | 97% |
bardoxolone
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating; | 100% |
bardoxolone
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating; | 89% |
bardoxolone
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating; | 81% |
bardoxolone
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating; | 74% |
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