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Hebei Nengqian Chemical Import and Export Co., LTD

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

Bardoxolone

Cas:218600-44-3

Min.Order:1 Kilogram

FOB Price: $1.0 / 10.0

Type:Trading Company

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Zhuozhou Wenxi import and Export Co., Ltd

WITH US,YOUR MONEY IN SAFE,YOUR BUSINESS IN SAFE 1)Quick Response Within 12 hours; 2)Quality Guarantee: All products are strictly tested by our QC, confirmed by QA and approved by third party lab in China, USA, Canada, Germany, UK, Italy, France et

Hot saleCAS 218600-44-3 with best price

Cas:218600-44-3

Min.Order:10 Gram

FOB Price: $146.0 / 176.0

Type:Trading Company

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Hubei CuiRan Biotechnology Co., Ltd

Hubei 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)

Bardoxolone

Cas:218600-44-3

Min.Order:10 Milligram

Negotiable

Type:Lab/Research institutions

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Zibo Hangyu Biotechnology Development Co., Ltd

Zibo 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

2-Cyano-3,12-dioxooleana-1,9-dien-28-oic acid

Cas:218600-44-3

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Xiamen Jenny Chemical Technology Co., Ltd.

GMP standard, high purity, competitive price, in stock 1. Quick Response: within 6 hours after receiving your email. 2. Quality Guarantee: All products are strictly tested by our QC, confirmed by QA, and approved by a third-party lab in China, USA,

Bardoxolone

Cas:218600-44-3

Min.Order:1 Milligram

Negotiable

Type:Trading Company

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Henan Allgreen Chemical Co.,Ltd

high quality Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea

2-Cyano-3,12-dioxooleana-1,9-dien-28-oic acid

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Antimex Chemical Limied

factory?direct?sale Application:Fine chemical intermediates, used as the main raw material for the synthesis of various pesticides, medicines, surfactants, polymer monomers, and antifungal agents

2-Cyano-3,12-dioxooleana-1,9-dien-28-oic acid

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Guangdong Juda Chemical Industrial Co.,Limited

Factory 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

218600-44-3 CAS No.218600-44-3

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Trading Company

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Hangzhou Fandachem Co.,Ltd

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

Oleana-1,9(11)-dien-28-oic acid, 2-cyano-3,12-dioxo-

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Other

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BOC Sciences

BOC 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:

Bardoxolone

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Trading Company

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Shanghai Yuanye Bio-Technology Co., Ltd.

good quality, competitive price, thoughtful after sale serviceAppearance:white powder Storage:Keep it in dry,shady and cool place Package:5mg Application:Pharma;Industry;Agricultural;chemical reaserch Transportation:by express or by sea Port:Any port

Bardoxolone

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Trading Company

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Chemlyte Solutions

factory?direct?sale Application:Fine chemical intermediates, used as the main raw material for the synthesis of various pesticides, medicines, surfactants, polymer monomers, and antifungal agents

2-Cyano-3,12-dioxooleana-1,9-dien-28-oic acid

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Other

inquiry

Chemsigma International Co.,Ltd.

bulk?production Application:Pharmaceutical intermediates

Amadis Chemical Co., Ltd.

1.Professional synthesis laboratory and production base. 2.Strong synthesis team and service team. 3.Professional data management system. 4.We provide the professional test date and product information ,ex. HNMR ,CNMR,FNMR, HPLC/G

Bardoxolone

Cas:218600-44-3

Min.Order:10 Milligram

Negotiable

Type:Lab/Research institutions

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Hebei Luspharm Trading Co.,Ltd

1. Best prices with satisfied quality; 2. Clients can choose the package's Courier (EMS, DHL, FedEx, UPS,TNT); 3.Clients can choose the packing way for his produccts from many recent effective packing ways; 4.Specials are poss

High quality Bardoxolone

Cas:218600-44-3

Min.Order:1 Gram

FOB Price: $1.0

Type:Trading Company

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Wuhan Sun-shine Bio-technology Corporation Limited

Wuhan Sun-shine Bio-technology Corporation Limited is specializing in the anticancer, antitumor,heart head blood-vessel,pharmaceutical intermediates,fine Chemicals production and customization. Company has strong ability of research and development

Bardoxolonewith factory price

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Changzhou Extraordinary Pharmatech co.,LTD

Changzhou 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

Bardoxolone

Cas:218600-44-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Wuhan New-Rise Biochem Co,. Ltd

1.High quality and competetive price 1)for prulifloxacin exported we can offer coa certificate and official invoice. 2)we are manufacturer with own lab and factory, can provide high quality products with factory price. 3)products purity is tes

High quality Bardoxolone

Cas:218600-44-3

Min.Order:1 Kilogram

Negotiable

Type:Trading Company

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suzhou BetterBioChem Co., Ltd.

Betterbiochem is specialized in APIs, pharmaceutical intermediates & fine chemicals. 1. The best quality, competitive price. 2. The best service before or after shipment. 3. Rich experience in export operation. 4. Rich experience in

RTA-401

Cas:218600-44-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Guangzhou PI & PI Biotech Inc. Ltd.

PI &PI Biotech Inc. provides great quality of APIs and Drug Impurities. Application:R & D

Bardoxolone

Cas:218600-44-3

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

U-Chemo Holding Co.,Limited

U-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

Bardoxolone

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai united Scientific Co.,Ltd.

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

2-Cyano-3,12-dioxooleana-1,9-dien-28-oic acid

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Nanjing Chemlin Chemical Co., Ltd.

Nanjing 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

218600-44-3

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Wuhan MoonZY Biological Technology Co.,Ltd

Superiority: 1. Quality: High purity, strict quality control, 10 years experience in chemical industry. 2. Price: Moderate price, more QTY more discount. 3. MOQ: Sample order is welcome to test quality. 4. Shipping time: In Stock, can be sh

Bardoxolone,218600-44-3

Cas:218600-44-3

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Wuhan Prominence Bio-technology Co., Ltd

Wuhan Prominence Bio-technology Co., Ltd is a leading provider and manufacturer of pharmaceutical and chemical products. Mainly involves API, pharmaceutical intermediates peditides and natural extract etc. We are capable to supply you with any quanti

Bardoxolone

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Wuxi Morality Chemical Co., Ltd

Do best quality products, erect the morality model Application:please email us, thanks

2-Cyano-3,12-dioxooleana-1,9-dien-28-oic acid

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Other

inquiry

Tianjin Tongde Biological Technology Co., Ltd.

2-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

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid

Cas:218600-44-3

Min.Order:0 Metric Ton

Negotiable

Type:Trading Company

inquiry

Shanghai Run-Biotech Co., Ltd.

1.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

Bardoxolone

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Sino Rarechem Labs Co.Ltd

We have two R&D center both in Suzhou and Nanjing. The R&D Center owns labs with 2500m466 Production Base. And excellent staff, advanced equipments ,instruments, strict quality management system enhance our competitiveness.We are good at rare&hard to

bardoxolone

Cas:218600-44-3

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Shanghai Caerulum Pharma Discovery Co.,Ltd

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

Bardoxolone

Cas:218600-44-3

Min.Order:25 Milligram

Negotiable

Type:Lab/Research institutions

inquiry

Synthetic route

bardoxolone methyl
218600-53-4

bardoxolone methyl

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
With lithium iodide In N,N-dimethyl-formamide71%
With lithium iodide In N,N-dimethyl-formamide71%
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
915710-94-0, 1244059-91-3, 1165931-54-3

tert‐butyl N‐[2‐(N‐hydroxycarbamimidoyl)ethyl]carbamate

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride
443104-14-1

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride

A

C39H54N4O5

C39H54N4O5

B

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
915710-94-0, 1244059-91-3, 1165931-54-3

tert‐butyl N‐[2‐(N‐hydroxycarbamimidoyl)ethyl]carbamate

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride
443104-14-1

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride

A

C39H56N4O6

C39H56N4O6

B

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;
3-methoxypropionamidoxime hydrochloride
67015-15-0

3-methoxypropionamidoxime hydrochloride

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride
443104-14-1

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride

A

C35H49N3O5

C35H49N3O5

B

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
With triethylamine; trimethylamine In dichloromethane at 20℃; Inert atmosphere;
methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate
65023-20-3

methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
218600-50-1

methyl 3,12-dioxoolean-9(11)-en-28-oate

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
65023-19-0

methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
218600-52-3

methyl 12-oxoisoxazolo[4,5-b]olean-9(11)-en-28-oate

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
1309236-68-7

2-cyano-3-hydroxy-12-oxoolean-2(3),9(11)-dien-28-oic acid

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
305818-39-7

methyl 2-hydroxymethylene-3,12-dioxoolean-9(11)-en-28-oate

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
305818-40-0

1,2-dihydro-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
methyl 2-cyano-3,12-dioxoolean-9(11)-en-28-oate

methyl 2-cyano-3,12-dioxoolean-9(11)-en-28-oate

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
1309236-68-7

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
1309943-46-1

2-cyano-3,12-dioxooleana-1,9(11)-diene-13β,28-lactone

B

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
218600-51-2

(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
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
508-02-1

Oleanolic acid

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
25493-69-0, 122798-61-2, 1721-57-9

(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
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
4339-72-4

oleanolic acid 3-acetate

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
25493-94-1

methyl 3-O-β-acetyl-11-dehydro-12-oxo-18β-oleanolate

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
1724-17-0, 73584-64-2

oleanolic acid methyl ester

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
69660-90-8

(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
218600-44-3

bardoxolone

Conditions
ConditionsYield
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
C31H43NO4

C31H43NO4

bardoxolone
218600-44-3

bardoxolone

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.333333h; Reflux;
bardoxolone
218600-44-3

bardoxolone

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride
443104-14-1

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane100%
With oxalyl dichloride In dichloromethane at 20℃;100%
With oxalyl dichloride In dichloromethane100%
bardoxolone
218600-44-3

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
1192122-92-1

(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
ConditionsYield
With diphenyl phosphoryl azide; triethylamine at 0 - 20℃;90%
With diphenyl phosphoryl azide; triethylamine In toluene at 20℃; for 6h;90%
bardoxolone
218600-44-3

bardoxolone

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide
572-09-8

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester

Conditions
ConditionsYield
With Aliquat 336; potassium carbonate In dichloromethane75%
With potassium carbonate; Aliquat 336 In dichloromethane; water75%
bardoxolone
218600-44-3

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
1191917-53-9

(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
ConditionsYield
With diethylamino-sulfur trifluoride In chloroform at 20℃; for 6.5h;94%
bardoxolone
218600-44-3

bardoxolone

C31H41NO5

C31H41NO5

Conditions
ConditionsYield
With dihydrogen peroxide In methanol; water; acetonitrile at 20℃; for 30h;90%
methanol
67-56-1

methanol

bardoxolone
218600-44-3

bardoxolone

bardoxolone methyl
218600-53-4

bardoxolone methyl

Conditions
ConditionsYield
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%
O2-(2,4-dinitro-5-(2-bromoethylamino)phenyl)-1-(piperidine-1-yl)diazen-1-ium-1,2-diolate

O2-(2,4-dinitro-5-(2-bromoethylamino)phenyl)-1-(piperidine-1-yl)diazen-1-ium-1,2-diolate

bardoxolone
218600-44-3

bardoxolone

O2-(2,4-dinitro-5-{2-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-oxoethylamino}phenyl)-1-(piperidine-1-yl)diazen-1-ium-1,2-diolate

O2-(2,4-dinitro-5-{2-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-oxoethylamino}phenyl)-1-(piperidine-1-yl)diazen-1-ium-1,2-diolate

Conditions
ConditionsYield
With potassium carbonate In acetone at 45℃; for 4h;68%
O2-(2,4-dinitro-5-(2-bromoethylamino)phenyl)-1-(N-methylethanolamino)diazen-1-ium-1,2-diolate

O2-(2,4-dinitro-5-(2-bromoethylamino)phenyl)-1-(N-methylethanolamino)diazen-1-ium-1,2-diolate

bardoxolone
218600-44-3

bardoxolone

O2-(2,4-dinitro-5-{2-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-oxoethylamino}phenyl)-1-(N-methylethanolamino)diazen-1-ium-1,2-diolate

O2-(2,4-dinitro-5-{2-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-oxoethylamino}phenyl)-1-(N-methylethanolamino)diazen-1-ium-1,2-diolate

Conditions
ConditionsYield
With potassium carbonate In acetone at 45℃; for 4h;74%
bardoxolone
218600-44-3

bardoxolone

C31H43NO4

C31H43NO4

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran84%
4-chloromethyl-5-methyl-1,3-dioxol-2-one
80841-78-7

4-chloromethyl-5-methyl-1,3-dioxol-2-one

bardoxolone
218600-44-3

bardoxolone

C36H45NO7

C36H45NO7

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating / reflux;83%
propionyl chloride
79-03-8

propionyl chloride

bardoxolone
218600-44-3

bardoxolone

1-isosorbide mononitrate 2-cyano-3-propionyloxy-12-oxoolean-2(3),9(11)-diene-28-carboxylic acid

1-isosorbide mononitrate 2-cyano-3-propionyloxy-12-oxoolean-2(3),9(11)-diene-28-carboxylic acid

Conditions
ConditionsYield
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%
acetyl chloride
75-36-5

acetyl chloride

bardoxolone
218600-44-3

bardoxolone

1-isosorbide mononitrate 2-cyano-3-acetoxy-12-oxoolean-2(3),9(11)-diene-28-carboxylic acid

1-isosorbide mononitrate 2-cyano-3-acetoxy-12-oxoolean-2(3),9(11)-diene-28-carboxylic acid

Conditions
ConditionsYield
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
218600-44-3

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
1192122-95-4

(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
ConditionsYield
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
218600-44-3

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
1192122-92-1

(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
1192122-95-4

(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
ConditionsYield
With diphenyl phosphoryl azide; triethylamine In toluene at 0 - 20℃; Overall yield = 94 %; Overall yield = 19.7 g;
bardoxolone
218600-44-3

bardoxolone

N-(2-(2-(2-(2-amidoethoxy)ethoxy)ethoxy)ethoxy)biotinamide
359860-27-8

N-(2-(2-(2-(2-amidoethoxy)ethoxy)ethoxy)ethoxy)biotinamide

11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid {2-[2-(2-{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethoxy}-ethoxy)-ethoxy]-ethyl}-amide

11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid {2-[2-(2-{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethoxy}-ethoxy)-ethoxy]-ethyl}-amide

Conditions
ConditionsYield
With 2`,3`-dideoxycytidine; dmap In dichloromethane at 20℃; for 48h;79%
bardoxolone
218600-44-3

bardoxolone

2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride
443104-14-1

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
1224947-97-0

2-cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 1.5h;96%
bardoxolone
218600-44-3

bardoxolone

benzyl halide

benzyl halide

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid benzyl ester

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid benzyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating;97%
bardoxolone
218600-44-3

bardoxolone

ethyl halide

ethyl halide

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid ethyl ester

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid ethyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating;100%
bardoxolone
218600-44-3

bardoxolone

n-octyl halide

n-octyl halide

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid octyl ester

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid octyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating;89%
bardoxolone
218600-44-3

bardoxolone

cyclopropylmethyl halide

cyclopropylmethyl halide

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid cyclopropylmethyl ester

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid cyclopropylmethyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating;81%
bardoxolone
218600-44-3

bardoxolone

n-butyl halide

n-butyl halide

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid butyl ester

(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid butyl ester

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating;74%

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