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Greenutra Resource Inc

Gossypol Acetate Extract Specification: Name: Gossypol Acetate Extract Identification Standardization Asp

Gossypol Acetate Extract

Cas:303-45-7

Min.Order:1 Kilogram

FOB Price: $25.0

Type:Trading Company

inquiry

Dayang Chem (Hangzhou) Co.,Ltd.

As a leading manufacturer and supplier of chemicals in China, DayangChem not only supply popular chemicals, but also DayangChem's R&D center offer custom synthesis services. DayangChem can provide different quantities of custom synthesis ch

Gossypol Manufacturer/High quality/Best price/In stock

Cas:303-45-7

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Xi'an Xszo Chem Co., Ltd.

1. Factory price and high quality must be guaranteed, base on 8 years of production and R&D experience2. Free samples will be provided,ensure specifications and quality are right for customer3. Customers will receive the most professional technical s

Factory Price API 99% GOSSYPOL 303-45-7 GMP Manufacturer

Cas:303-45-7

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

inquiry

Hebei yanxi chemical co.,LTD.

chengdu and import and export trade co., LTD., who registered capital of 10 million yuan, nearly to $2 million, we have a pharmaceutical raw materials factory production of pharmaceutical raw materials, and a reagent r&d center, and we do res

GOSSYPOL

Cas:303-45-7

Min.Order:1000 Gram

FOB Price: $500.0

Type:Trading Company

inquiry

Henan Tianfu Chemical Co., Ltd.

Product Name: GOSSYPOL Synonyms: 1,1',6,6',7,7'-HEXAHYDROXY-3,3'-DIMETHYL-5,5'-BIS(1-METHYLETHYL)-[2,2'-BINAPHTHALENE]-8,8'-DICARBOXALDEHYDE;2,2'-BIS[8-FORMYL-1

GOSSYPOL 303-45-7

Cas:303-45-7

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

With our good experience, we offer detailed technical support and advice to assist customers. We communicate closely with customers to establish their quality requirements. Consistent Quality Our plant has strict quality control in each manufacturin

Gossypol :303-45-7

Cas:303-45-7

Min.Order:1 Kilogram

FOB Price: $3.0 / 10.0

Type:Trading Company

inquiry

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

Manufacturer supply CAS 303-45-7 with best quality

Cas:303-45-7

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

Hangzhou Sartort Biopharma Co., Ltd

Appearance:Brownish-yellow powder Storage:R.T Package:1kg/Bottle or at customers requirement Application:It has an antitumor effect and can be used as a male contraceptive Transportation:Express/Sea/Air Port:Any port in China

Factory Producer 98% Gossypol powder CAS 303-45-7

Cas:303-45-7

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

Shanghai Upbio Tech Co.,Ltd

1.No Less 8 years exporting experience. Clients can 100% received goods 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Upbio is Specialized

Qingdao Beluga Import and Export Co., LTD

GOSSYPOL CAS:303-45-7 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates, ste

GOSSYPOL CAS:303-45-7

Cas:303-45-7

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Shandong Hanjiang Chemical Co., Ltd.

Hello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai

Gossypol

Cas:303-45-7

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

inquiry

Henan Wentao Chemical Product Co., Ltd.

Henan Wentao Chemical Product Co.,Ltd is Located in Zhengzhou High-tech Development Zone with import and export license, We passed ISO 9001:2008 as well, Henan Wentao has developed more than 1000 compounds, which are widely used in the fields of prod

Chengdu Biopurify Phytochemicals Ltd.

Chengdu Biopurify Phytochemicals 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 Medic

Gossypol 303-45-7

Cas:303-45-7

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Keyingchem Co.,Ltd

Hangzhou KeyingChem Co., Ltd. exported this product to many countries and regions at best price. If you are looking for the material’s manufacturer or supplier in China, KeyingChem is your best choice. Pls contact with us freely for getting det

GOSSYPOL

Cas:303-45-7

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Hangzhou Lingrui Chemical Co.,Ltd.

advantage: 1. The best price, satisfactory quality; 2. customers have the right to choose the delivery of parcels (EMS, DHL, FedEx, UPS); 3. customers have the right to choose from the recent effective packaging methods of their products packaging

Manufacturer/High quality Gossypol 303-45-7

Cas:303-45-7

Min.Order:1 Gram

Negotiable

Type:Other

inquiry

Hangzhou J&H Chemical Co., Ltd.

J&H CHEM R&D center can offer custom synthesis according to the contract research and development services for the fine chemicals, pharmaceutical, biotechnique and some of the other chemicals. J&H CHEM has some Manufacturing base in Jia

Shaanxi Cuicheng Biomedical Technology Co., Ltd.

Why Choose Us: 1. Factory direct sales, so we can provide the competitive price and high quality product base on 8 years of production and R&D experience. 2. It is available in stock for quick shipment.Products could be packaged according to cu

GOSSYPOL

Cas:303-45-7

Min.Order:1 Gram

Negotiable

Type:Other

inquiry

Shanghai Massive Chemical Technology Co., Ltd.

Massive Chemical is certified with ISO9001 and ISO14001 manufacturer for this product. We will offer all documents as requirement for the materials which includes, Certificate of Analysis, Material Safety Data Sheet, and Method of Analysis and

GOSSYPOL

Cas:303-45-7

Min.Order:1 Gram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

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

GOSSYPOL

Cas:303-45-7

Min.Order:10 Gram

FOB Price: $100.0

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,

Gossypol

Cas:303-45-7

Min.Order:1 Milligram

Negotiable

Type:Trading Company

inquiry

Hangzhou Huarong Pharm Co., Ltd.

Hangzhou Huarong Pharm Co., Ltd.established since 2006 , has been actively developing specialty products for Finished Dosages, APIs, Intermediates, and Fine chemicals markets in North America, Europe, Korea, Japan, Mid-East and all over the World. Hu

Gossypol

Cas:303-45-7

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Hunan chemfish Pharmaceutical co.,Ltd

Appearance:95%+ Package:R&D,Pilot run Transportation:per client require Port:Express ,Air, Sea

Gossypol

Cas:303-45-7

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

shanghai Tauto Biotech Co., Ltd

The quality is guaranteed. If you find the product is wrong compared with COA, we promise 100% refund or change product. COA and HPLC will be shipped out with goods. You can also inform your analysis method and we will follow your analysi

E-0874 gossypol

Cas:303-45-7

Min.Order:0 Metric Ton

Negotiable

Type:Manufacturers

inquiry

Bluecrystal chem-union

We are a Union of chemistry in China, consists of chemists,engineers, laboratories,factories in China. We organize surplus capacity of R&D and production as well as custom synthesis for chemical products and chemical business project. We are supp

Gossypol CAS 303-45-7

Cas:303-45-7

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Kono Chem Co.,Ltd

high purity lowest priceAppearance:solid or liquid Storage:in sealed air resistant place Package:drum and bag Application:for pharma use Transportation:by sea or air Port:Beijing or Guangzhou

gossypol

Cas:303-45-7

Min.Order:0

Negotiable

Type:Other

inquiry

GIHI CHEMICALS CO.,LIMITED

high purity,in stock Package:25kg/drum,or as per customers'demand Application:API,or Intermediates,fine chemicals Transportation:air,sea,courier

Gossypol

Cas:303-45-7

Min.Order:0

Negotiable

Type:Lab/Research institutions

inquiry

Sinoway Industrial Co., Ltd.

Why is SINOWAY:1) Specialized in pharmaceutical and healthcare industrial since 19872) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days.4) We have warehouse in USA with quickly shipment . Application:API

99% up by HPLC GOSSYPOL 303-45-7

Cas:303-45-7

Min.Order:0

Negotiable

Type:Trading Company

inquiry

Shanghai Acmec Biochemical Technology Co., Ltd.

Acmec is a leading manufacturer and supplier of biochemical reagents and life science products. We have over 40,000 items in stock (real-time inventory) and offer discounted prices to registered members of the online store ( www.acmec.com.cn ) Appea

Acmec Gossypol 100mg

Cas:303-45-7

Min.Order:1 bottle

Negotiable

Type:Lab/Research institutions

inquiry

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

gossypol

Cas:303-45-7

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Chengdu Lemeitian Pharmaceutical Technology Co,. Ltd

ADVANTAGE:1. More than 3,000 Chinese medicine reference substances / standard products available from stock, issued on the same day, multiple cities can be delivered the next day2. The products are provided with COA, HPLC, NMR, quality assurance, pac

Gossypol

Cas:303-45-7

Min.Order:0

Negotiable

Type:Manufacturers

inquiry

Synthetic route

(±)-gossypol acetic acid
5453-04-3, 866541-93-7, 1189561-66-7

(±)-gossypol acetic acid

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With iron(III) chloride In acetone at 60℃;85%
In diethyl ether; water at 25℃; for 0.166667h; Temperature; Solvent; Sonication;105 mg
2,3,8-trihydroxy-4-isopropyl-6-methyl-1-naphthaldehyde
40817-07-0

2,3,8-trihydroxy-4-isopropyl-6-methyl-1-naphthaldehyde

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 4h; Inert atmosphere;76.1%
With tert-butyl peroxyacetate In 1,2-dichloro-ethane at 80℃; for 2.5h; Temperature; Inert atmosphere;52%
With tert-butyl peroxyacetate In 1,2-dichloro-ethane; mineral oil at 80℃; for 2.5h; Inert atmosphere; Schlenk technique;41%
With laccase of Coriolus versicolor; oxygen at 30℃; pH=5.5; aq. phosphate buffer;
apogossypol
784206-41-3

apogossypol

N,N'-diphenylformamidine
864131-95-3

N,N'-diphenylformamidine

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydroquinone at 180℃; under 5 - 15 Torr; for 2.5h;72%
apogossypol
784206-41-3

apogossypol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With Dichloromethyl methyl ether; titanium tetrachloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;37%
4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one)
73728-76-4

4,4'-dihydroxy-5,5'-diisopropyl-7,7'-dimethyl-bis(3H-naphtho[1,8-bc]furan-3-one)

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
In water; acetone for 48h;
Conditions
ConditionsYield
With hydrogenchloride In ethanol at 25℃; Kinetics; Mechanism; Thermodynamic data; other temperatures, ΔH(excit.), ΔS(excit.), ΔG(excit.);
sulfuric acid
7664-93-9

sulfuric acid

dianilogossipol
6952-36-9

dianilogossipol

(rac)-gossypol
303-45-7

(rac)-gossypol

3-(1H-indol-3-yl)-2-[(1,6,1',6'-tetrahydroxy-8'-{[2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-methylene}-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-8-ylidenemethyl)-amino]-propionic acid methyl ester

3-(1H-indol-3-yl)-2-[(1,6,1',6'-tetrahydroxy-8'-{[2-(1H-indol-3-yl)-1-methoxycarbonyl-ethylamino]-methylene}-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-8-ylidenemethyl)-amino]-propionic acid methyl ester

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In diethyl ether Heating;
C54H54N4O10

C54H54N4O10

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In diethyl ether Heating;
4-isopropyl-3,8-dimethoxy-1,6-dimethylnaphthalen-2-ol

4-isopropyl-3,8-dimethoxy-1,6-dimethylnaphthalen-2-ol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: silver(l) oxide / methanol / 3 h / 20 °C
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1: silver(l) oxide / 2 h / Reflux
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: silver(l) oxide / methanol / 3 h / 20 °C
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1: silver(l) oxide / 2 h / Reflux
2: potassium carbonate / acetone / 5 h / 20 °C
3: dichloromethane / 0.5 h / 20 °C
4: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
5: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
6: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
7: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
8: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C18H24O4

C18H24O4

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: potassium carbonate / acetone / 5 h / 20 °C
2: dichloromethane / 0.5 h / 20 °C
3: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
5: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
6: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1: potassium carbonate / acetone / 5 h / 20 °C
2: dichloromethane / 0.5 h / 20 °C
3: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
5: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
6: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
7: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
1-isopropyl-2,3,5-trimethoxy-4-(methoxymethyl)-7-methylnaphthalene

1-isopropyl-2,3,5-trimethoxy-4-(methoxymethyl)-7-methylnaphthalene

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: dichloromethane / 0.5 h / 20 °C
2: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
4: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1: dichloromethane / 0.5 h / 20 °C
2: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
4: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
5: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
6: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique
1.2: 20 °C / Inert atmosphere; Schlenk technique
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
3.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
4.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 4 steps
1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
2: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h
3: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
(4-isopropyl-2,3,8-trimethoxy-6-methylnaphthalen-1-yl)methanol

(4-isopropyl-2,3,8-trimethoxy-6-methylnaphthalen-1-yl)methanol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
2: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
2: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
3: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
2: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 3 steps
1: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h
2: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
4-isopropyl-2,3,8-trimethoxy-6-methyl-1-naphthaldehyde
50399-96-7

4-isopropyl-2,3,8-trimethoxy-6-methyl-1-naphthaldehyde

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
2: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
3: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 2 steps
1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
4-hydroxy-5-isopropyl-7-methylnaphtho[1,8-bc]furan-3-one
1256723-09-7

4-hydroxy-5-isopropyl-7-methylnaphtho[1,8-bc]furan-3-one

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
2: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
2-hydroxy-6-isopropyl-3-methyl-benzaldehyde
1665-99-2

2-hydroxy-6-isopropyl-3-methyl-benzaldehyde

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / methanol / 3 h / 20 °C
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 17 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / 2 h / Reflux
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 18 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / methanol / 3 h / 20 °C
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 18 steps
1.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
2.1: potassium carbonate / acetone / 15 h / 30 °C
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
3.2: 2 h / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
5.2: 10 h / -78 - -30 °C / Inert atmosphere
6.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
7.1: acetic anhydride; sodium acetate / 2 h / Reflux
8.1: sodium hydroxide / methanol; water / Reflux
9.1: potassium carbonate / acetone / 12 h / 20 °C
10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
10.2: 10 h / 20 °C
11.1: silver(l) oxide / 2 h / Reflux
12.1: potassium carbonate / acetone / 5 h / 20 °C
13.1: dichloromethane / 0.5 h / 20 °C
14.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
15.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
16.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
17.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
carvacrol
499-75-2

carvacrol

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / methanol / 3 h / 20 °C
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 18 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / 2 h / Reflux
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 19 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / methanol / 3 h / 20 °C
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
19.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 19 steps
1.1: tin(IV) chloride; triethylamine / toluene / 0.33 h / 20 °C / Inert atmosphere
1.2: 8 h / 100 °C / Inert atmosphere
2.1: acetic acid; bromine / 20.25 h / 20 °C / Cooling with ice
3.1: potassium carbonate / acetone / 15 h / 30 °C
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
4.2: 2 h / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
6.2: 10 h / -78 - -30 °C / Inert atmosphere
7.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
8.1: acetic anhydride; sodium acetate / 2 h / Reflux
9.1: sodium hydroxide / methanol; water / Reflux
10.1: potassium carbonate / acetone / 12 h / 20 °C
11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
11.2: 10 h / 20 °C
12.1: silver(l) oxide / 2 h / Reflux
13.1: potassium carbonate / acetone / 5 h / 20 °C
14.1: dichloromethane / 0.5 h / 20 °C
15.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
16.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
17.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
18.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
19.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C11H13BrO2

C11H13BrO2

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / methanol / 3 h / 20 °C
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 16 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / 2 h / Reflux
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 17 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / methanol / 3 h / 20 °C
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 17 steps
1.1: potassium carbonate / acetone / 15 h / 30 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
2.2: 2 h / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
4.2: 10 h / -78 - -30 °C / Inert atmosphere
5.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
6.1: acetic anhydride; sodium acetate / 2 h / Reflux
7.1: sodium hydroxide / methanol; water / Reflux
8.1: potassium carbonate / acetone / 12 h / 20 °C
9.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
9.2: 10 h / 20 °C
10.1: silver(l) oxide / 2 h / Reflux
11.1: potassium carbonate / acetone / 5 h / 20 °C
12.1: dichloromethane / 0.5 h / 20 °C
13.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
15.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
16.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
17.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C24H26O5

C24H26O5

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / methanol / 3 h / 20 °C
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / 2 h / Reflux
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / 2 h / Reflux
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
2.2: 10 h / 20 °C
3.1: silver(l) oxide / methanol / 3 h / 20 °C
4.1: potassium carbonate / acetone / 5 h / 20 °C
5.1: dichloromethane / 0.5 h / 20 °C
6.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
8.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C18H19BrO2

C18H19BrO2

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / methanol / 3 h / 20 °C
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 15 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / 2 h / Reflux
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 16 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / methanol / 3 h / 20 °C
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 16 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 20 °C
1.2: 2 h / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
3.2: 10 h / -78 - -30 °C / Inert atmosphere
4.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
5.1: acetic anhydride; sodium acetate / 2 h / Reflux
6.1: sodium hydroxide / methanol; water / Reflux
7.1: potassium carbonate / acetone / 12 h / 20 °C
8.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
8.2: 10 h / 20 °C
9.1: silver(l) oxide / 2 h / Reflux
10.1: potassium carbonate / acetone / 5 h / 20 °C
11.1: dichloromethane / 0.5 h / 20 °C
12.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
13.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
14.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
15.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
16.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C20H23F3O5

C20H23F3O5

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
3: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
4: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
3: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
4: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C17H19BrO2

C17H19BrO2

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / methanol / 3 h / 20 °C
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 14 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / 2 h / Reflux
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 15 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / methanol / 3 h / 20 °C
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 15 steps
1.1: potassium carbonate / acetone / 12 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
2.2: 10 h / -78 - -30 °C / Inert atmosphere
3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
4.1: acetic anhydride; sodium acetate / 2 h / Reflux
5.1: sodium hydroxide / methanol; water / Reflux
6.1: potassium carbonate / acetone / 12 h / 20 °C
7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
7.2: 10 h / 20 °C
8.1: silver(l) oxide / 2 h / Reflux
9.1: potassium carbonate / acetone / 5 h / 20 °C
10.1: dichloromethane / 0.5 h / 20 °C
11.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
12.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
13.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
14.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
15.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
2-(benzyloxy)-5-bromo-4-isopropyl-3-methoxy-1-methylbenzene

2-(benzyloxy)-5-bromo-4-isopropyl-3-methoxy-1-methylbenzene

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / methanol / 3 h / 20 °C
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 13 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / 2 h / Reflux
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 14 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / methanol / 3 h / 20 °C
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 14 steps
1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 10 h / -78 - -30 °C / Inert atmosphere
2.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
3.1: acetic anhydride; sodium acetate / 2 h / Reflux
4.1: sodium hydroxide / methanol; water / Reflux
5.1: potassium carbonate / acetone / 12 h / 20 °C
6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
6.2: 10 h / 20 °C
7.1: silver(l) oxide / 2 h / Reflux
8.1: potassium carbonate / acetone / 5 h / 20 °C
9.1: dichloromethane / 0.5 h / 20 °C
10.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
12.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
13.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
14.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C19H22O3

C19H22O3

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / methanol / 3 h / 20 °C
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / 2 h / Reflux
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 13 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / methanol / 3 h / 20 °C
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 13 steps
1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C
2.1: acetic anhydride; sodium acetate / 2 h / Reflux
3.1: sodium hydroxide / methanol; water / Reflux
4.1: potassium carbonate / acetone / 12 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
5.2: 10 h / 20 °C
6.1: silver(l) oxide / 2 h / Reflux
7.1: potassium carbonate / acetone / 5 h / 20 °C
8.1: dichloromethane / 0.5 h / 20 °C
9.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
11.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
12.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C24H28O6

C24H28O6

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / methanol / 3 h / 20 °C
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / 2 h / Reflux
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / methanol / 3 h / 20 °C
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 12 steps
1.1: acetic anhydride; sodium acetate / 2 h / Reflux
2.1: sodium hydroxide / methanol; water / Reflux
3.1: potassium carbonate / acetone / 12 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
4.2: 10 h / 20 °C
5.1: silver(l) oxide / 2 h / Reflux
6.1: potassium carbonate / acetone / 5 h / 20 °C
7.1: dichloromethane / 0.5 h / 20 °C
8.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
10.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
11.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
12.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C26H28O6

C26H28O6

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / methanol / 3 h / 20 °C
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / 2 h / Reflux
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / methanol / 3 h / 20 °C
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: sodium hydroxide / methanol; water / Reflux
2.1: potassium carbonate / acetone / 12 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
3.2: 10 h / 20 °C
4.1: silver(l) oxide / 2 h / Reflux
5.1: potassium carbonate / acetone / 5 h / 20 °C
6.1: dichloromethane / 0.5 h / 20 °C
7.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
9.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
10.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
11.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
methyl 6-(benzyloxy)-8-isopropyl-4,7-dimethoxy-5-methyl-2-naphthoate

methyl 6-(benzyloxy)-8-isopropyl-4,7-dimethoxy-5-methyl-2-naphthoate

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / 2 h / Reflux
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / methanol / 3 h / 20 °C
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / 2 h / Reflux
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
Multi-step reaction with 9 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C
1.2: 10 h / 20 °C
2.1: silver(l) oxide / methanol / 3 h / 20 °C
3.1: potassium carbonate / acetone / 5 h / 20 °C
4.1: dichloromethane / 0.5 h / 20 °C
5.1: lithium hydroxide / water; tetrahydrofuran / 1 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C
7.1: boron tribromide / dichloromethane / 6 h / -78 - -10 °C / Inert atmosphere
8.1: hydrogenchloride / water; acetonitrile / 5 h / 20 °C
9.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 4 h / 80 °C / Inert atmosphere
View Scheme
C24H30O5

C24H30O5

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1.1: sodium tetrahydroborate; methanol / 0.5 h / 0 °C / Inert atmosphere; Schlenk technique
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 0 °C / Inert atmosphere; Schlenk technique
2.2: 14 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
3.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 32 h / 20 °C / Schlenk technique
4.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere; Schlenk technique
4.2: 2 h / 20 °C / Inert atmosphere; Schlenk technique
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 4 h / 20 °C / Inert atmosphere; Schlenk technique
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
7.1: 2,6-di-tert-butyl-4-methyl-phenol / chlorobenzene / 13 h / 160 °C / Schlenk technique; Inert atmosphere
8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
9.1: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere; Schlenk technique
10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique
10.2: 20 °C / Inert atmosphere; Schlenk technique
11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
12.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
13.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
C18H24O4

C18H24O4

(rac)-gossypol
303-45-7

(rac)-gossypol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate / acetonitrile / 20 h / 80 °C / Inert atmosphere; Schlenk technique
2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique
2.2: 20 °C / Inert atmosphere; Schlenk technique
3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Schlenk technique
4.1: boron tribromide / dichloromethane / 10 h / -78 - -10 °C / Inert atmosphere; Schlenk technique
5.1: tert-butyl peroxyacetate / 1,2-dichloro-ethane; mineral oil / 2.5 h / 80 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 5 steps
1: potassium carbonate / acetonitrile / 4 h / 80 °C
2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C
3: 2-Iodobenzoic acid / dimethyl sulfoxide / 12 h
4: boron tribromide / dichloromethane / 10 h / -78 - -10 °C
5: tert-butyl peroxyacetate / 1,2-dichloro-ethane / 2.5 h / 80 °C / Inert atmosphere
View Scheme
(rac)-gossypol
303-45-7

(rac)-gossypol

L-Phenylalaninol
3182-95-4

L-Phenylalaninol

8,8'-Bis-((S)-4-benzyl-oxazolidin-2-yl)-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

8,8'-Bis-((S)-4-benzyl-oxazolidin-2-yl)-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In methanol for 5h; Ambient temperature;100%
(rac)-gossypol
303-45-7

(rac)-gossypol

C54H54N4O10

C54H54N4O10

C54H54N4O10

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 45℃; for 2h; Resolution of racemate;A 99.4%
B 95%
heptane-1,7-diamine
646-19-5

heptane-1,7-diamine

(rac)-gossypol
303-45-7

(rac)-gossypol

8,8'-Bis-[1-(7-amino-heptylamino)-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

8,8'-Bis-[1-(7-amino-heptylamino)-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

Conditions
ConditionsYield
With acid In ethanol for 3h; Heating;98.7%
(rac)-gossypol
303-45-7

(rac)-gossypol

Glycyrrhizin ammonium
53956-04-0

Glycyrrhizin ammonium

C42H62O16*C30H30O8*H3N

C42H62O16*C30H30O8*H3N

Conditions
ConditionsYield
at 20℃;98%
(rac)-gossypol
303-45-7

(rac)-gossypol

C54H54N4O10

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol Reflux;98%
(rac)-gossypol
303-45-7

(rac)-gossypol

C54H54N4O10
132303-09-4

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol Reflux;98%
(rac)-gossypol
303-45-7

(rac)-gossypol

C54H54N4O10

C54H54N4O10

C54H54N4O10

C54H54N4O10

Conditions
ConditionsYield
With sodium hydroxide In ethanol at 20℃; for 0.5h;A 97%
B 94%
(rac)-gossypol
303-45-7

(rac)-gossypol

ethylamine
75-04-7

ethylamine

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine
307976-02-9

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-ethylimine

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;96%
With isopropyl alcohol
(rac)-gossypol
303-45-7

(rac)-gossypol

isopropylamine
75-31-0

isopropylamine

5,5'-Diisopropyl-8,8'-bis-[(E)-isopropylimino-methyl]-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-8,8'-bis-[(E)-isopropylimino-methyl]-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;96%
(rac)-gossypol
303-45-7

(rac)-gossypol

megosin

megosin

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 3h; Heating;95.8%
(rac)-gossypol
303-45-7

(rac)-gossypol

5-Aminosalicylic Acid
89-57-6

5-Aminosalicylic Acid

gossypolydenebis-N-(3-carboxy-4-hydroxyaniline)

gossypolydenebis-N-(3-carboxy-4-hydroxyaniline)

Conditions
ConditionsYield
In ethanol for 3h; Heating;95.31%
(rac)-gossypol
303-45-7

(rac)-gossypol

apogossypol
784206-41-3

apogossypol

Conditions
ConditionsYield
Stage #1: (rac)-gossypol With sodium hydroxide; acetic acid In water at 90℃; for 3.5h; darkness;
Stage #2: With sulfuric acid In water at 0℃;
95%
Stage #1: (rac)-gossypol With water; sodium hydroxide at 90℃; for 3.5h; Inert atmosphere; Darkness;
Stage #2: With sulfuric acid In water Cooling with ice;
95%
Stage #1: (rac)-gossypol With sodium hydroxide In water at 90℃; for 3.5h; Inert atmosphere; Darkness;
Stage #2: With sulfuric acid In water
95%
(rac)-gossypol
303-45-7

(rac)-gossypol

methylamine
74-89-5

methylamine

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-methyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-methyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In N,N-dimethyl-formamide Condensation;95%
(rac)-gossypol
303-45-7

(rac)-gossypol

4-hydroxynon-2-enal
850480-50-1

4-hydroxynon-2-enal

5,5'-dihydroxy-2,2'-bis((E)-3-hydroxyoct-1-en-1-yl)-9,9'-diisopropyl-7,7'-dimethyl-[6,6'-binaphtho[2,3-d][1,3]dioxole]-4,4'-dicarbaldehyde

5,5'-dihydroxy-2,2'-bis((E)-3-hydroxyoct-1-en-1-yl)-9,9'-diisopropyl-7,7'-dimethyl-[6,6'-binaphtho[2,3-d][1,3]dioxole]-4,4'-dicarbaldehyde

Conditions
ConditionsYield
With zinc(II) chloride In acetonitrile at 60℃; for 5h; Reagent/catalyst; Solvent; Temperature;93.5%
1.3-propanedithiol
109-80-8

1.3-propanedithiol

(rac)-gossypol
303-45-7

(rac)-gossypol

8,8'-bis-[1,3]dithian-2-yl-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

8,8'-bis-[1,3]dithian-2-yl-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
Stage #1: 1.3-propanedithiol; (rac)-gossypol In chloroform at 20℃; for 1h;
Stage #2: With boron trifluoride diethyl etherate In chloroform at 20℃; for 15h;
93%
glucosamine
14257-69-3

glucosamine

(rac)-gossypol
303-45-7

(rac)-gossypol

C36H41NO12

C36H41NO12

Conditions
ConditionsYield
In methanol at 20℃; for 3h; Inert atmosphere;92.9%
Conditions
ConditionsYield
In methanol at 20℃; for 3h; Inert atmosphere;92.6%
p-Aminohippuric acid
61-78-9

p-Aminohippuric acid

(rac)-gossypol
303-45-7

(rac)-gossypol

(4-{[8'-[1-[4-(Carboxymethyl-carbamoyl)-phenylamino]-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-(8Z)-ylidenemethyl]-amino}-benzoylamino)-acetic acid

(4-{[8'-[1-[4-(Carboxymethyl-carbamoyl)-phenylamino]-meth-(Z)-ylidene]-1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-7,7'-dioxo-7',8'-dihydro-7H-[2,2']binaphthalenyl-(8Z)-ylidenemethyl]-amino}-benzoylamino)-acetic acid

Conditions
ConditionsYield
With acid In ethanol for 3h; Heating;92.3%
propylamine
107-10-8

propylamine

(rac)-gossypol
303-45-7

(rac)-gossypol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-propyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-[(E)-propyliminomethyl]-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;92%
2-phenylpropylamine
582-22-9

2-phenylpropylamine

(rac)-gossypol
303-45-7

(rac)-gossypol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(E)-2-phenyl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(E)-2-phenyl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;92%
(rac)-gossypol
303-45-7

(rac)-gossypol

pentafluorophenyl hydrazine
828-73-9

pentafluorophenyl hydrazine

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-(pentafluorophenyl-hydrazonomethyl)-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-(pentafluorophenyl-hydrazonomethyl)-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In ethanol for 3h; Heating;91.9%
(rac)-gossypol
303-45-7

(rac)-gossypol

N-Aminoanabasine
86133-36-0

N-Aminoanabasine

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-ylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol
86133-35-9

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3,4,5,6-tetrahydro-2H-[2,3']bipyridinyl-1-ylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In ethanol Heating;91%
n-Dodecylamine
124-22-1

n-Dodecylamine

(rac)-gossypol
303-45-7

(rac)-gossypol

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-dodecylimine
5463-57-0

1,6,7,1',6',7'-hexahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthyl-8,8'-dicarbaldehyde bis-dodecylimine

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;91%
(rac)-gossypol
303-45-7

(rac)-gossypol

gossypolone
4547-72-2

gossypolone

Conditions
ConditionsYield
Stage #1: (rac)-gossypol With iron(III) chloride; acetic acid In water; acetone at 100℃; for 2h;
Stage #2: With sulfuric acid In diethyl ether; water
91%
With iron(III) chloride In acetic acid; acetone at 60 - 70℃; Oxidation;49%
With iron(III) chloride; acetic acid In acetone at 70℃; for 0.75h;
(rac)-gossypol
303-45-7

(rac)-gossypol

C7H10N2O5(2-)*2Na(1+)

C7H10N2O5(2-)*2Na(1+)

C37H38N2O12(2-)*2Na(1+)

C37H38N2O12(2-)*2Na(1+)

Conditions
ConditionsYield
With sodium hydroxide In methanol at 20℃; for 3h; pH=7.4; Inert atmosphere;90.8%
4-aminophthalimide
3676-85-5

4-aminophthalimide

(rac)-gossypol
303-45-7

(rac)-gossypol

gossypolydenebis-N-(3-iminophthalimide)

gossypolydenebis-N-(3-iminophthalimide)

Conditions
ConditionsYield
In ethanol for 3h; Heating;90.17%
4'-aminobenzo-15-crown-5-ether
60835-71-4

4'-aminobenzo-15-crown-5-ether

(rac)-gossypol
303-45-7

(rac)-gossypol

1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8,8'-bis-[(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-ylamino)-methylene]-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

1,6,1',6'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-8,8'-bis-[(6,7,9,10,12,13,15,16-octahydro-5,8,11,14,17-pentaoxa-benzocyclopentadecen-2-ylamino)-methylene]-8H,8'H-[2,2']binaphthalenyl-7,7'-dione

Conditions
ConditionsYield
In ethanol for 6h; Heating;90.1%
4-(3-Aminopropyl)morpholine
123-00-2

4-(3-Aminopropyl)morpholine

(rac)-gossypol
303-45-7

(rac)-gossypol

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3-morpholin-4-yl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol
104757-46-2

5,5'-Diisopropyl-3,3'-dimethyl-8,8'-bis-{[(Z)-3-morpholin-4-yl-propylimino]-methyl}-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In isopropyl alcohol Heating;90%
(rac)-gossypol
303-45-7

(rac)-gossypol

isobutylamine
78-81-9

isobutylamine

8,8'-Bis-[(E)-isobutylimino-methyl]-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

8,8'-Bis-[(E)-isobutylimino-methyl]-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,6,7,1',6',7'-hexaol

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;90%
(rac)-gossypol
303-45-7

(rac)-gossypol

N-butylamine
109-73-9

N-butylamine

GSBN

GSBN

Conditions
ConditionsYield
In diethyl ether; isopropyl alcohol at 20 - 45℃; for 2.08333h; Condensation;90%

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