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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

High Quality 99% Bimatoprost 155206-00-1 GMP Manufacturer

Cas:155206-00-1

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

inquiry

Henan Tianfu Chemical Co., Ltd.

Our 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

Bimatoprost 155206-00-1

Cas:155206-00-1

Min.Order:1 Metric Ton

FOB Price: $500.0

Type:Lab/Research institutions

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Chemvon Biotechnology Co. Ltd.

Chemvon 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

Bimatoprost

Cas:155206-00-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Sinoway Industrial Co., Ltd.

Why is SINOWAY: 1) Specialized in pharmaceutical and healthcare industrial for 34 years. 2) 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 . 5) We c

99.5% Bimatoprost powder

Cas:155206-00-1

Min.Order:1 Gram

FOB Price: $150.0

Type:Trading Company

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Hebei Nengqian Chemical Import and Export Co., LTD

Our 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

CAS 155206-00-1 Bimatoprost

Cas:155206-00-1

Min.Order:1 Gram

FOB Price: $12.0 / 15.0

Type:Trading Company

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Hubei Yuanmeng Biological Technology Co., Ltd.

Hubei 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

99% Bimatoprost CAS 155206-00-1 with Best Price

Cas:155206-00-1

Min.Order:1 Kilogram

FOB Price: $3.0 / 5.0

Type:Trading Company

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Taizhou Crene Biotechnology co.ltd

Our 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-

Bimatoprost 155206-00-1

Cas:155206-00-1

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

inquiry

Qiuxian Yanjia Trading Co., Ltd

Advantages 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

Bimatoprost eyelash growth CAS 155206-00-1 bimatoprost

Cas:155206-00-1

Min.Order:1 box

FOB Price: $190.0 / 220.0

Type:Trading Company

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DALIAN BAIJIA IMPORT AND EXPORT CO., LTD

Dalian Bajia import and export co. ltd have great engineer make more great quality cargo will meet all customer request . Now we have own lab for cargo even my cargo is so less but quality and quantity and shippment will be promise as we are pro

Bimatoprost

Cas:155206-00-1

Min.Order:0 Metric Ton

Negotiable

Type:Lab/Research institutions

inquiry

Dayang Chem (Hangzhou) Co.,Ltd.

DayangChem 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

Bimatoprost Manufacturer/High quality/Best price/In stock

Cas:155206-00-1

Min.Order:1 Kilogram

FOB Price: $3.0

Type:Lab/Research institutions

inquiry

Hangzhou Dingyan Chem Co., Ltd

Analysis tests Standard Results Appearance White to off white solid white solid Purity by HPLC

High purity Various Specifications Bimatoprost CAS:155206-00-1

Cas:155206-00-1

Min.Order:1 Gram

FOB Price: $100.0 / 500.0

Type:Manufacturers

inquiry

Kono Chem Co.,Ltd

Specifications CAS No.: 155206-00-1 Other Names: / MF: C25H37NO4 EINECS No.: / Place of Origin: Shaanxi, China (Mainland)

Bimatoprost 99% powder

Cas:155206-00-1

Min.Order:1 Gram

Negotiable

Type:Other

inquiry

Wuhan Fortuna Chemical Co.,Ltd

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

Factory supply Bimatoprost Cas 155206-00-1 with high quality competitive price

Cas:155206-00-1

Min.Order:1 Gram

FOB Price: $700.0 / 735.0

Type:Trading Company

inquiry

Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Jinlan 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

bimatoprost cas 155206-00-1 to control the progression of glaucoma

Cas:155206-00-1

Min.Order:1 Gram

Negotiable

Type:Manufacturers

inquiry

Xi'an Quanao Biotech Co., Ltd.

Xi’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

Cosmetic grade 99% bimatoprost powder for eyelash growing CAS 155206-00-1

Cas:155206-00-1

Min.Order:5 Gram

FOB Price: $179.0 / 199.0

Type:Manufacturers

inquiry

Hefei TNJ chemical industry co.,ltd

Bimatoprost 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

Factory Directly Supplying Bimatoprost, CAS No. 155206-00-1

Cas:155206-00-1

Min.Order:100 Gram

Negotiable

Type:Trading Company

inquiry

Hangzhou Think Chemical Co. Ltd

Bimatoprost[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

Bimatoprost with competitive price

Cas:155206-00-1

Min.Order:1 Gram

Negotiable

Type:Other

inquiry

Henan Allgreen Chemical Co.,Ltd

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

Bimatoprost

Cas:155206-00-1

Min.Order:1 Kilogram

Negotiable

Type:Manufacturers

inquiry

Ality Chemical Corporation

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

Factory Supply Bimatoprost

Cas:155206-00-1

Min.Order:1

Negotiable

Type:Other

inquiry

Xi`an Eastling Biotech Co., Ltd.

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 &

Factory high quality Bimatoprost GMP

Cas:155206-00-1

Min.Order:1 Gram

FOB Price: $159.0 / 170.0

Type:Lab/Research institutions

inquiry

Shanghai Seasonsgreen Chemical Co.,Ltd

Shanghai 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

lower price High quality Bimatoprost

Cas:155206-00-1

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Manufacturers

inquiry

Hebei yanxi chemical co.,LTD.

hebei 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

HP1003 USP EP Standard CAS 155206-00-1 Bimatoprost powder CAS NO.155206-00-1

Cas:155206-00-1

Min.Order:1 Metric Ton

FOB Price: $1.0 / 3.0

Type:Trading Company

inquiry

Chemwill Asia Co., Ltd.

Our main production base is located in Xuzhou industry park. We are certified both to the ISO 9001 and ISO 14001 Standards, have a safety management system in place.Our R&D team masters core technology for process-design of target building block

Bimatoprost

Cas:155206-00-1

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

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

New production CAS 155206-00-1 with best quality

Cas:155206-00-1

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

inquiry

Hubei Vanz Pharm Co.,Ltd

MOQ: 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

Bulk bimatoprost Powder cas 155206-00-1

Cas:155206-00-1

Min.Order:1 Gram

Negotiable

Type:Trading Company

inquiry

Henan Sinotech Import&Export Corporation

Name: 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

Leader Biochemical Group

PRODUCT DETAILS

China Largest Manufacturer factory Supply Bimatoprost CAS 155206-00-1

Cas:155206-00-1

Min.Order:1 Kilogram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

inquiry

Hubei Langyou International Trading Co., Ltd

1. 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

99% CAS 155206-00-1 Tenoxicam API yellow crystalline powder

Cas:155206-00-1

Min.Order:100 Gram

Negotiable

Type:Other

inquiry

Shanghai Upbio Tech Co.,Ltd

1,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

High quality Bimatoprost

Cas:155206-00-1

Min.Order:1 Gram

FOB Price: $1.0

Type:Lab/Research institutions

inquiry

Xi'an Faithful Biotech Co., Ltd.

We are the manufacturers and suppliers of API in China, and warehouse in Germany and USA of California, which can quickly and safely deliver to your address 1.High quality and competitive price. 2.Free sample for your evaluation. 3.Promptly delivery

Intermediate 99% Purity Bimatoprost Raw Material API Powder Bimatoprost raw Powder

Cas:155206-00-1

Min.Order:10 Gram

FOB Price: $9.0

Type:Trading Company

inquiry

Synthetic route

(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
1240483-19-5

(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
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
1430731-70-6

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
75-04-7

ethylamine

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
1393740-68-5

(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
With hydrogenchloride; water In tetrahydrofuran at 20℃; for 22h;86%
2,2-bis(hydroxymethyl)propyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate

2,2-bis(hydroxymethyl)propyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-5-phenyl-1-pentenyl]cyclopentyl]-5-heptenoate

ethylamine
75-04-7

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
1163135-95-2

(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
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
75-04-7

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
38315-47-8

(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
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
856240-62-5

(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
1201226-16-5

(5-(ethylamino)-5-oxopentyl)triphenylphosphonium bromide

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
960056-50-2

(9S,11R,15S)-9,11,15-trihydroxy-17-phenyl-18,19,20-trinor-5Z,13E-prostadienoate

ethylamine
75-04-7

ethylamine

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
856240-52-3

(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
155206-00-1

bimatoprost

Conditions
ConditionsYield
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%
C23H30O4

C23H30O4

ethylamine
75-04-7

ethylamine

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
With trimethylaluminum In tetrahydrofuran at 20 - 40℃; for 18h; Product distribution / selectivity;67.3%
propylamine
107-10-8

propylamine

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester
130209-76-6

15α-hydroxy-17-phenyl-18,19,20-trinorprostaglandin F2α isopropyl ester

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
1194047-64-7

(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
1194396-71-8

(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

B

C31H46ClNO5

C31H46ClNO5

C

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
856240-62-5

(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
1163135-95-2

(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
155206-00-1

bimatoprost

Conditions
ConditionsYield
With sodium hexamethyldisilazane
C28H40O6

C28H40O6

ethylamine
75-04-7

ethylamine

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
In dichloromethane at -10℃; for 2h; Inert atmosphere;
C26H36O7

C26H36O7

ethylamine
75-04-7

ethylamine

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
In dichloromethane at -10℃; for 2h;
bimataprost L-arginine salt
1224443-45-1

bimataprost L-arginine salt

ethylamine
75-04-7

ethylamine

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
329313-36-2

(S)-tert-butyldimethyl(5-phenylpent-1-yn-3-yloxy)silane

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
C31H52O3Si2

C31H52O3Si2

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
C31H54O3Si2

C31H54O3Si2

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
C37H62O4Si2

C37H62O4Si2

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
C35H58O4Si2

C35H58O4Si2

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
C17H27IOSi

C17H27IOSi

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
98974-31-3

(R)-2-allyl-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
17814-85-6

(4-carboxybutyl)triphenylphosphonium bromide

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
1240483-16-2

(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
41723-91-5

4-carboxybutyliden triphenylphosphorane sodium

ethylamine
75-04-7

ethylamine

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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;
(3aR,4R,5R,6aS)-4-((E)-3-hydroxy-5-phenylpent-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

(3aR,4R,5R,6aS)-4-((E)-3-hydroxy-5-phenylpent-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
1240483-15-1

(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-one

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
(3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-5-hydroxy-4-((E)-3-hydroxy-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2-one

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
C30H50O4Si2

C30H50O4Si2

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
1300092-89-0

(3aR,4R,5R,6aS)-4-((S,E)-3-((2-methoxyethoxy)methoxy)-5-phenylpent-1-enyl)hexahydro-2H-cyclopenta[b]furan-2,5-diol

bimatoprost
155206-00-1

bimatoprost

Conditions
ConditionsYield
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
4426-47-5

butylboronic acid

bimatoprost
155206-00-1

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
1194047-63-6

(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
ConditionsYield
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;
propionic acid anhydride
123-62-6

propionic acid anhydride

bimatoprost
155206-00-1

bimatoprost

15-propionyl-bimatoprost
1393740-64-1

15-propionyl-bimatoprost

Conditions
ConditionsYield
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%
acetyl chloride
75-36-5

acetyl chloride

bimatoprost
155206-00-1

bimatoprost

15-acetyl-bimatoprost
1393740-67-4

15-acetyl-bimatoprost

Conditions
ConditionsYield
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
535-17-1, 3853-80-3, 18668-00-3, 6034-46-4

(S)-2-acetoxypropionic acid

bimatoprost
155206-00-1

bimatoprost

(S)-2-acetoxypropionic acid (1S,2R,3R,4R)-4-((S)-2-acetoxypropionyloxy)-3-[(E)-(S)-3-((S)-2-acetoxypropionyloxy)-5-phenylpent-1-enyl]-2-((Z)-6-ethylcarbamoylhex-2-enyl)cyclopentyl

(S)-2-acetoxypropionic acid (1S,2R,3R,4R)-4-((S)-2-acetoxypropionyloxy)-3-[(E)-(S)-3-((S)-2-acetoxypropionyloxy)-5-phenylpent-1-enyl]-2-((Z)-6-ethylcarbamoylhex-2-enyl)cyclopentyl

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;72%
t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

bimatoprost
155206-00-1

bimatoprost

(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol
1393740-68-5

(3aR,4R,5R,6aS)-4-[(3R)-(tert-butyldimethylsilyl)oxy-5-phenylpentyl]perhydrocyclopenta[b]furan-2,5-diol

Conditions
ConditionsYield
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
155206-00-1

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
1163135-96-3

(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
ConditionsYield
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%
(S)-2-((S)-2-{(S)-2-[(S)-2-((S)-2-acetoxypropionyloxy)propionyloxy]propionyloxy}propionyloxy)propionic acid

(S)-2-((S)-2-{(S)-2-[(S)-2-((S)-2-acetoxypropionyloxy)propionyloxy]propionyloxy}propionyloxy)propionic acid

bimatoprost
155206-00-1

bimatoprost

C59H81NO26

C59H81NO26

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;59%
(2S)‐2‐{[(2S)‐2‐(acetyloxy)propanoyl]oxy}propanoic acid

(2S)‐2‐{[(2S)‐2‐(acetyloxy)propanoyl]oxy}propanoic acid

bimatoprost
155206-00-1

bimatoprost

C41H57NO14

C41H57NO14

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;52%
(S)-2-{(S)-2-[(S)-2-((S)-2-acetoxypropionyloxy)propionyloxy]propionyloxy}propionic acid

(S)-2-{(S)-2-[(S)-2-((S)-2-acetoxypropionyloxy)propionyloxy]propionyloxy}propionic acid

bimatoprost
155206-00-1

bimatoprost

C53H73NO22

C53H73NO22

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 30℃; for 2h; Inert atmosphere;47%
(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoic acid

(2S)-2-{[(2S)-2-{[(2S)-2-(acetyloxy)propanoyl]oxy}propanoyl]oxy}propanoic acid

bimatoprost
155206-00-1

bimatoprost

C47H65NO18

C47H65NO18

Conditions
ConditionsYield
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
1194047-73-8

4-(nitrooxy)butyl 4-chloro-4-oxobutanoate

bimatoprost
155206-00-1

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
1194047-48-7

(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
ConditionsYield
With DMAP resin (PS-DMAP) In dichloromethane at 0 - 20℃; for 72.3333h; Inert atmosphere;30%
4-(nitrooxy)butyl 4-nitrophenyl carbonate
935472-60-9

4-(nitrooxy)butyl 4-nitrophenyl carbonate

bimatoprost
155206-00-1

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
1194047-46-5

(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
1194047-45-4

(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
1194047-56-7

(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
1194047-57-8

(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
1194047-55-6

(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
ConditionsYield
With dmap In dichloromethane at 20℃; for 60h; Inert atmosphere;A 2%
B 15%
C 18%
D 4%
E 5%
4-chlorobutyl chloroformate
37693-18-8

4-chlorobutyl chloroformate

bimatoprost
155206-00-1

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
1194047-69-2

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
ConditionsYield
With dmap In dichloromethane at 20℃; for 72h; Inert atmosphere;15%
6-(nitrooxy)hexanoyl chloride
907625-06-3

6-(nitrooxy)hexanoyl chloride

bimatoprost
155206-00-1

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
1194047-41-0

(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
1194047-42-1

(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
1194047-44-3

(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]
1194047-43-2

(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
ConditionsYield
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
927-58-2

4-bromobutyroyl chloride

bimatoprost
155206-00-1

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
1194047-71-6

(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
ConditionsYield
With dmap In dichloromethane at 0℃; for 72h; Inert atmosphere;6%
succinic acid anhydride
108-30-5

succinic acid anhydride

bimatoprost
155206-00-1

bimatoprost

C29H41NO7
1043914-34-6

C29H41NO7

Conditions
ConditionsYield
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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