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
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inquiryOur company was built in 2009 with an ISO certificate.In the past 6 years, we have grown up as a famous fine chemicals supplier in China and we had established stable business relationships with Samsung,LG,Merck,Thermo Fisher Scientific and so on.Our
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inquiryChemvon Biotechnology is one of the leading high-technology manufacturer in the field of pharmaceutical and fine chemical industry. From origins as a research group in technology service, chemvon has progressed into an integrated company with a k
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inquiryOur advantages: 1. All inquiries will be replied within 12 hours. 2. Dedication to quality, supply & service. 3. Strictly on selecting raw materials. 4. Reasonable & competitive price, fast lead time. 5. Sample is available for your eva
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inquiryHubei Yuanmeng Biological Technology Co., Ltd., which is located in Wuhan, China. We are specializing in the exportation of APIs, and plant extracts ect. Our products has been exported to America, Australia, Brazil, the Europe, Middle East and other
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inquiryOur company provides one-stop services of research - development - production for a variety of special prouducts. Not only do we make effective use of our strong technological strength, but also establish of cooperative relations with several well-
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inquiryAdvantages 1, High quality with competitive price: 1) Standard:BP/USP/EP/Enterprise standard 2) All Purity≥99% 3) We are manufacturer and can provide high quality products with factory price. 2, Fast and safe delivery 1) Parcel can be sent
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inquiryDayangChem exported this product to many countries and regions at best price. If you are looking for the material's manufacturer or supplier in China, DayangChem is your best choice. Pls contact with us freely for getting detailed product spe
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inquiryAnalysis tests Standard Results Appearance White to off white solid white solid Purity by HPLC
Cas:155206-00-1
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inquirySpecifications CAS No.: 155206-00-1 Other Names: / MF: C25H37NO4 EINECS No.: / Place of Origin: Shaanxi, China (Mainland)
Unique advantages for Bimatoprost Cas 155206-00-1 Guaranteed purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:White powder Storage:?20°C Package:100mg/vial;1g/bottle or foil bag Appli
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inquiryJinlan Pharm-Drugs Technology Co.,Limited (with its export company Hangzhou Royall Import & Export Co.,Ltd.)is located in Hangzhou, Zhejiang Province. Neighboring Ningbo port, Shanghai port, Hangzhou Xiaoshan Int’l Airport and Shanghai Pu
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inquiryXi’an Quanao Biotech Co., Ltd. with 18 years experience in plant extract filed. Product grade: Medicine, Health care product, Cosmetics, Food, Beverage, Feed. Hot selling market: Europe, North America, South America, Middle East, Asia Pacifi
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inquiryBimatoprost Basic information Product Name: Bimatoprost Synonyms: N-ETHYL-9ALPHA,11ALPHA,15S-TRIHYDROXY-17-PHENYL-18,19,20-TRINOR-PROSTA-5Z, 13E-DIEN-1-AMIDE;LUMIGAN;BIMATOPROST;BIMATOPR
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inquiryBimatoprost[CAS:155206-00-1] Latanoprost[CAS:130209-82-4] HANGZHOU THINK CHEMICAL CO., LTD. (THINKCHEM) is an integrative corporation of trade, research and contract manufacture. With about ten years of business experiences on
high quality Appearance:White or off-white Solid Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea Port:shanghai
The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi
155206-00-1 - Physico-chemical Properties Molecular Formula C25H37NO4 Molar Mass 415.57 Density 1.145±0.06 g/cm3(Predicted) Melting Point 66-68°C Boling Point 629.8±55.0 &
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inquiryShanghai Seasonsgreen Chemical is a high-tech research and development, production, sale and custom synthesis set in one high-tech chemical products enterprises. Our sales and marketing division is located in Shanghai, serving international pharmaceu
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inquiryhebei yanxi chemical 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 research and developm
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inquiryMOQ: 1g Form: Powder Colour: White Test: HPLC Function: anti hair loss Grade: Pharm Appearance:white Storage:room Package:drum Application:anti hair loss Port:Shangh
Cas:155206-00-1
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inquiryName: CAS: 155206-00-1 Molecular formula: C25H37NO4 Molecular weight: 415.5656 Appearance:White Powder Storage:Store in cool and dry place, away from sun light
Cas:155206-00-1
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inquiryPRODUCT DETAILS
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inquiry1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:yellow crystalline powder Storage:Store in sealed containers
Cas:155206-00-1
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inquiry1,In No Less five years exporting experience. 2.Lower Price with higher quality 3,Free sample 4,We are sincerely responsible for the "product quality" and "After Service" Appearance: white powder Storage:dry and cool place
Cas:155206-00-1
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inquiry(Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide
bimatoprost
Conditions | Yield |
---|---|
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide With hydrogenchloride; water In tetrahydrofuran at 20℃; for 18h; Stage #2: In tetrahydrofuran pH=6.8; Aqueous phosphate buffer; | 91% |
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide With hydrogenchloride In tetrahydrofuran; water at 20℃; for 18h; Stage #2: In tetrahydrofuran; water pH=6.8; Aqueous phosphate buffer; | 91% |
Stage #1: (Z)-7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-enyl)-5-hydroxycyclopentyl)-N-ethylhept-5-enamide With ammonium hydrogen difluoride In tetrahydrofuran at 20 - 40℃; for 24h; Inert atmosphere; Stage #2: With water In tetrahydrofuran; tert-butyl methyl ether Product distribution / selectivity; | 80% |
With hydrogenchloride; water In methanol at 15 - 20℃; |
2,2-bis(hydroxymethyl)propyl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate
ethylamine
bimatoprost
Conditions | Yield |
---|---|
In water at 20℃; for 72h; | 87.2% |
(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol
bimatoprost
Conditions | Yield |
---|---|
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 22h; | 86% |
ethylamine
A
(5E)-N-ethyl-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]-cyclopentyl]hept-5-enamide
B
bimatoprost
Conditions | Yield |
---|---|
In water at 20℃; for 72h; Overall yield = 87.2 %; Overall yield = 8.12 g; | A n/a B 83.7% |
In water for 60h; | A n/a B 73% |
ethylamine
(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-((S)-(E)-3-hydroxy-5-phenylpent-1-enyl)-cyclopentyl]hept-5-enoic acid methyl ester
bimatoprost
Conditions | Yield |
---|---|
In methanol at 24 - 27℃; for 72h; Product distribution / selectivity; | 80% |
In water at 20℃; for 60h; | 62% |
In methanol; water at 90℃; for 45h; |
(3aR,4R,5R,6aS)-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2,5-diol
(5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide
bimatoprost
Conditions | Yield |
---|---|
Stage #1: (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere; Stage #2: (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol In tetrahydrofuran at 20℃; for 4h; Reagent/catalyst; Temperature; Inert atmosphere; | 80% |
Stage #1: (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Stage #2: (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide In tetrahydrofuran at 0℃; | 65% |
Stage #1: (5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide With potassium tert-butylate In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere; Stage #2: (3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; | 41% |
(9S,11R,15S)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienoate
ethylamine
bimatoprost
Conditions | Yield |
---|---|
With water at 20℃; for 60h; | 80% |
(5Z)-N-ethyl-7-((1R,2R,3R,5S)-5-hydroxy-2-((3S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enamide
bimatoprost
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol at 20℃; for 2h; | 77.5% |
With toluene-4-sulfonic acid In methanol at 20℃; for 2h; | 77.5% |
Conditions | Yield |
---|---|
With trimethylaluminum In tetrahydrofuran at 20 - 40℃; for 18h; Product distribution / selectivity; | 67.3% |
propylamine
15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
bimatoprost
Conditions | Yield |
---|---|
In methanol at 90℃; | 62% |
(S,E)-1-((1S,5R,6R,7R)-3-butyl-7-((Z)-7-(ethylamino)-7-oxohept-2-en-1-yl)-2,4-dioxa-3-borabicyclo[3.2.1]octan-6-yl)-5-phenylpent-1-en-3-yl 6-bromohexanoate
A
(1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxo-2-hepten-1-yl]-3,5-dihydroxycyclopentyl]-1-(2-phenylethyl)-2-propen-1-yl-hexanoic acid 6-(nitrooxy)ester
C
bimatoprost
Conditions | Yield |
---|---|
With silver nitrate In acetonitrile at 20 - 25℃; for 38h; | A n/a B n/a C 4.27% |
(3aR,4R,5R,6aS)-4-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]-hexahydro-2H-cyclopenta[b]furan-2,5-diol
A
(5E)-N-ethyl-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]-cyclopentyl]hept-5-enamide
B
bimatoprost
Conditions | Yield |
---|---|
With sodium hexamethyldisilazane |
Conditions | Yield |
---|---|
In dichloromethane at -10℃; for 2h; Inert atmosphere; |
Conditions | Yield |
---|---|
In dichloromethane at -10℃; for 2h; |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide Product distribution / selectivity; | |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; N,N-dimethyl-formamide Product distribution / selectivity; |
(S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: Schwartz's reagent / tetrahydrofuran / 3 h / 20 °C / Darkness 1.2: -78 - -20 °C 1.3: 0.5 h / -78 °C 2.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 2.2: -50 °C 3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: Schwartz's reagent / tetrahydrofuran / 3 h / 20 °C / Darkness 1.2: -78 - -20 °C 1.3: 0.5 h / -78 °C 2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere 3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 5.1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere 6.1: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 6 steps 1.1: Schwartz's reagent / tetrahydrofuran / 3 h / 20 °C / Darkness 1.2: -78 - -20 °C 1.3: 0.5 h / -78 °C 2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere 3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C View Scheme |
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 1.2: -50 °C 2.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 3.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 4.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 5.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 1.2: -50 °C 2.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 3.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 4.1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere 5.1: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere 2: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 4: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere 5: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 5 steps 1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere 2: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 3: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 4: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 5: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C View Scheme |
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 2: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 3: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 4: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C View Scheme | |
Multi-step reaction with 4 steps 1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 2: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 3: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere 4: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere View Scheme |
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 3: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C View Scheme | |
Multi-step reaction with 3 steps 1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 2: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere 3: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere View Scheme |
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 2: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C View Scheme | |
Multi-step reaction with 2 steps 1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere 2: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere View Scheme |
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 1.2: 0.75 h / -78 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 2.2: -50 °C 3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 1.2: 0.75 h / -78 °C / Inert atmosphere 2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere 3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 5.1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere 6.1: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 6 steps 1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 1.2: 0.75 h / -78 °C / Inert atmosphere 2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere 3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 1.2: 0.75 h / -78 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 2.2: -50 °C 3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 5.1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere 6.1: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere View Scheme |
(R)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 1.2: 0.75 h / -78 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / toluene / 3 h / -78 °C 2.2: -50 °C 3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 1.2: 0.75 h / -78 °C / Inert atmosphere 2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere 3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 5.1: tetrahydrofuran / 27 h / 20 - 40 °C / Reflux; Inert atmosphere 6.1: ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 6 steps 1.1: n-butyllithium / hexane; tert-butyl methyl ether / 2 h / -78 °C / Inert atmosphere 1.2: 0.75 h / -78 °C / Inert atmosphere 2.1: L-Selectride / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere 3.1: dmap; diisopropyl-carbodiimide / tetrahydrofuran / 24 h / 20 - 40 °C / Inert atmosphere 4.1: Grubbs catalyst first generation / dichloromethane / 18 h / 20 - 40 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride; ammonium hydrogen difluoride / tetrahydrofuran / 24 h / 20 - 40 °C 6.1: trimethylaluminum / tetrahydrofuran / 18 h / 20 - 40 °C View Scheme |
(4-carboxybutyl)triphenylphosphonium bromide
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran / 20 °C / Inert atmosphere 2.1: tetrahydrofuran / -10 °C / Inert atmosphere 2.2: 15 - 30 °C / Cooling View Scheme | |
Multi-step reaction with 3 steps 1.1: potassium carbonate / acetone / 10 h / 20 °C 2.1: bromine / water / 60 h / 25 °C 3.1: potassium tert-butylate / tetrahydrofuran / 0.67 h / 0 °C 3.2: 0 °C View Scheme |
(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-ol
4-carboxybutyliden triphenylphosphorane sodium
ethylamine
bimatoprost
Conditions | Yield |
---|---|
Stage #1: (3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-ol; 4-carboxybutyliden triphenylphosphorane sodium In tetrahydrofuran at -10℃; Inert atmosphere; Stage #2: With water; ammonium chloride In tetrahydrofuran; n-heptane; ethyl acetate at 15 - 30℃; Cooling; Stage #3: ethylamine Product distribution / selectivity; |
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: potassium carbonate; methanol / 15 h / 20 °C 1.2: 4 h / 20 - 31 °C 1.3: 4 h / 20 °C / pH ~ 1 2.1: 1H-imidazole / dmap / N,N-dimethyl-formamide / 15 h / 20 °C 3.1: water; methanol / 0 - 20 °C / Resolution of diastereomers 4.1: diisobutylaluminium hydride / toluene / -40 °C / Inert atmosphere 4.2: 20 °C 5.1: tetrahydrofuran / -10 °C / Inert atmosphere 5.2: 15 - 30 °C / Cooling View Scheme |
(3aR,4R,5R,6aS)-5-((tert-butyldimethylsilyl)oxy)-4-((S,E)-3-((tert-butyldimethylsilyl)oxy)-5-phenylpent-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: diisobutylaluminium hydride / toluene / -40 °C / Inert atmosphere 1.2: 20 °C 2.1: tetrahydrofuran / -10 °C / Inert atmosphere 2.2: 15 - 30 °C / Cooling View Scheme | |
Multi-step reaction with 5 steps 1.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -30 °C / Inert atmosphere 1.2: -30 °C 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 2.2: 3.25 h / 0 - 20 °C 3.1: potassium carbonate / acetone / 18 h / 20 °C 4.1: water / tetrahydrofuran / 52 h / 20 °C 5.1: hydrogenchloride / water; tetrahydrofuran / 18 h / 20 °C 5.2: pH 6.8 / Aqueous phosphate buffer View Scheme |
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 1H-imidazole / dmap / N,N-dimethyl-formamide / 15 h / 20 °C 2.1: water; methanol / 0 - 20 °C / Resolution of diastereomers 3.1: diisobutylaluminium hydride / toluene / -40 °C / Inert atmosphere 3.2: 20 °C 4.1: tetrahydrofuran / -10 °C / Inert atmosphere 4.2: 15 - 30 °C / Cooling View Scheme |
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: water; methanol / 0 - 20 °C / Resolution of diastereomers 2.1: diisobutylaluminium hydride / toluene / -40 °C / Inert atmosphere 2.2: 20 °C 3.1: tetrahydrofuran / -10 °C / Inert atmosphere 3.2: 15 - 30 °C / Cooling View Scheme |
(3aR,4R,5R,6aS)-4-((S,E)-3-((2-methoxyethoxy)methoxy)-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol
bimatoprost
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere 1.2: 1.5 h / 25 °C / Inert atmosphere 1.3: pH 5 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetone / 8 h / 25 °C / Inert atmosphere 3.1: water / 24 h / 25 °C 4.1: sodium iodide; cerium(III) chloride heptahydrate / acetonitrile / 2 h / 80 - 85 °C View Scheme |
butylboronic acid
bimatoprost
(Z)-7-[(1S,5R,6R,7R)-3-butyl-6-[((E,3S)-3-hydroxy-5-phenylpent-1-enyl)]-2,4-dioxa-3-borabicyclo[3.2.1]octan-7-yl]-N-ethylhept-5-enamide
Conditions | Yield |
---|---|
In dichloromethane at 42℃; for 1h; Product distribution / selectivity; Inert atmosphere; | 100% |
In tert-butyl methyl ether at 40℃; for 1h; Solvent; | |
In tert-butyl methyl ether at 40℃; for 1h; Solvent; Temperature; Inert atmosphere; |
Conditions | Yield |
---|---|
Stage #1: bimatoprost With butylboronic acid In dichloromethane for 0.666667h; Reflux; Stage #2: propionic acid anhydride With dmap; triethylamine In dichloromethane at 20℃; Cooling with ice; | 88% |
Conditions | Yield |
---|---|
Stage #1: bimatoprost With butylboronic acid In dichloromethane for 4h; Reflux; Stage #2: acetyl chloride With pyridine In dichloromethane at 0℃; for 3h; | 76% |
(S)-2-acetoxypropionic acid
bimatoprost
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere; | 72% |
t-butyldimethylsiyl triflate
bimatoprost
(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol
Conditions | Yield |
---|---|
Stage #1: bimatoprost With butylboronic acid In dichloromethane for 0.666667h; Reflux; Stage #2: t-butyldimethylsiyl triflate With 2,6-dimethylpyridine In dichloromethane at 20℃; Cooling with ice; | 64% |
bimatoprost
(5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E)-3-oxo-5-phenylpent-1-en-1-yl]cyc!opentyl}-N-ethylhept-5-enamide
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane; dichloromethane at 40℃; for 24h; | 63% |
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 20℃; Inert atmosphere; | 50% |
bimatoprost
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere; | 59% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere; | 52% |
bimatoprost
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere; | 47% |
bimatoprost
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere; | 42% |
4-(nitrooxy)butyl 4-chloro-4-oxobutanoate
bimatoprost
(1R,2R,3R,4S)-3-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 4-(nitrooxy)butyl butanedioate
Conditions | Yield |
---|---|
With DMAP resin (PS-DMAP) In dichloromethane at 0 - 20℃; for 72.3333h; Inert atmosphere; | 30% |
4-(nitrooxy)butyl 4-nitrophenyl carbonate
bimatoprost
A
(1S,2E)-3-{(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-3,5-dihydroxycyclopentyl}-1-(2-phenylethyl)prop-2-en-1-yl 4-(nitrooxy)butyl carbonate
B
(2R,3R)-3-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 4-(nitrooxy)butyl carbonate
C
(1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-3-hydroxy-5-({[4-(nitrooxy)butoxy]carbonyl}oxy)cyclopentyl]-1-(2-phenylethyl)prop-2-en-1-yl 4-(nitrooxy)butyl carbonate
D
(1R,3S,4R,5R)-4-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-5-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentane-1 ,3-diyl bis[4-(nitrooxy)butyl] biscarbonate
E
(1R,3S,4R,5R)-4-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-5-[(1E,3S)-3-({[4-(nitrooxy)butoxy]carbonyl}oxy)-5-phenylpent-1-en-1-yl]cyclopentane-1,3-diyl bis[4-(nitrooxy)butyl]biscarbonate
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 60h; Inert atmosphere; | A 2% B 15% C 18% D 4% E 5% |
4-chlorobutyl chloroformate
bimatoprost
4-chlorobutyl (2R,3R)-3-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl carbonate
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 72h; Inert atmosphere; | 15% |
6-(nitrooxy)hexanoyl chloride
bimatoprost
A
(1R,2R,3R,4S)-3-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 6-(nitrooxy)hexanoate
B
(1S,2R,3R,4R)-2-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-3-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 6-(nitrooxy)hexanoate
C
(1S,2E)-3-[(1R,2R,3S,5R)-2-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-3-hydroxy-5-{[6-(nitrooxy)hexanoyl]oxy}cyclopentyl]-1-(2-phenylethyl)prop-2-en-1-yl 6-(nitrooxy)hexanoate
D
(1R,3S,4R,5R)-4-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-5-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentane-1,3-diyl bis[6-(nitrooxy)hexanoate]
Conditions | Yield |
---|---|
With DMAP resin (PS-DMAP) In dichloromethane at 0 - 20℃; for 18.3333h; Inert atmosphere; | A 12.4% B 1.7% C n/a D n/a |
4-bromobutyroyl chloride
bimatoprost
(1R,2R,3R,4S)-3-[(2Z)-7-(ethylamino)-7-oxohept-2-en-1-yl]-4-hydroxy-2-[(1E,3S)-3-hydroxy-5-phenylpent-1-en-1-yl]cyclopentyl 4-bromobutanoate
Conditions | Yield |
---|---|
With dmap In dichloromethane at 0℃; for 72h; Inert atmosphere; | 6% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 0.333333h; | |
With dmap; triethylamine In dichloromethane at 20℃; for 1h; Product distribution / selectivity; |
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