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ACHIEVER SYSTEAM BIOCHEM CO., LTD.

We are specialized in custom synthesis, chemical/pharmaceutical/ pesticides outsourcing and contract research. We are committed to provide excellence in researching, manufacturing and drug discovery process. Our research team of scientists co

2-Azetidinone, 1-(4-fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(phenylmethoxy)phenyl]-, (3R,4S)-

Cas:163222-32-0

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

Simagchem Corporation

Welcome to Simagchem, your partner in China as a premier supply of bulk specialty chemicals for industry and life science. We introduce experienced quality product and exceptional JIT service with instant market intelligence in China to benefit our

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

Henan Allgreen Chemical Co.,Ltd

Good quality Good price Promptly delivery Appearance:white powder Storage:dry dondition Application:intermediate Port:shanghai

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

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

(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-(4-phenylmethoxy)-phenyl]-2-azetidinone

Cas:163222-32-0

Min.Order:5 Kiloliter

FOB Price: $1.2 / 5.0

Type:Manufacturers

inquiry

Hebei Nengqian Chemical Import and Export Co., LTD

Our Advantage Rich Experience Our products are sold all over Europe,North&South America, Sino-East, Asia and pacific area as well as Africa,we establish long term. Quality service Company cooperates with research institutes. We strictly con

Henan Tianfu Chemical Co., Ltd.

Our company was built in 2009 with an ISO certificate.In the past 5 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.O

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 163222-32-0 with best quality

Cas:163222-32-0

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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

Hangzhou Huarong Pharm Co., Ltd.

Hangzhou Huarong Pharm Co., Ltd. established since 2009 , has been always focusing on supplying products and services to our clients in the field of small molecule drug. Huarong Pharm has built platforms for the research, development and manufac

(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(phenylmethoxy)phenyl]-2-azetidinone(ZTB-8)

Cas:163222-32-0

Min.Order:1 Gram

FOB Price: $1.0 / 2.0

Type:Lab/Research institutions

inquiry

Qingdao Beluga Import and Export Co., LTD

(3R,4S)-4-(4-(Benzyloxy)Phenyl)-1-(4-Fluorophenyl)-3-((S)-3-(4- Fluorophenyl)-3-Hydroxypropyl)Azetidin-2-One CAS:163222-32-0 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development,

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

Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Ezetimibe intermediate CAS:163222-32-0 Specification:in-house Stock:Fresh Purity:98% min Application:163222-32-0 Port:FOB China

Ezetimibe intermediate cas 163222-32-0

Cas:163222-32-0

Min.Order:10 Gram

FOB Price: $5.0

Type:Trading Company

inquiry

Xiamen Hisunny Chemical Co.,Ltd

Best quality & Attractive price & Professional service; Trial & Pilot & Commercial Hisunny Chemical is a leading manufacturer and supplier of chemicals in China. We develop produce and distribute high quality intermediates, specia

Triumph International Development Limilted

Appearance:Off-White Solid Storage:Store in a cool,dry place and keep away from direct strong light Package:As customer request Application:Used for research and industrial manufacture. Transportation:Common products:Sea/Air/Cou

Afine Chemicals Limited

Our Services 1. New Molecules R&D 2. Own test center HPLC NMR GC LC-MS 3. API and Intermediates from China reputed manufacturers 4. Documents support COA MOA MSDS DMF open part Our advantages 1. Government awarded company. Top 100 enter

(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-fluorophenyl)-3-hydroxypropyl]-4-[4-(phenylmethoxy)phenyl]-2-azetidinone

Cas:163222-32-0

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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

HANWAYS CHEMPHARM CO.,LIMITED

We are concentrating on APIs and pharmaceutical intermediates. It is made obtainable from us at the most reasonable rate. Our Service: 1. Rich experience: Our company is a professional production leading factory in China in pharmaceutical are

Chemlyte Solutions

Chemlyte Solutions believe that customers and suppliers deserve much more than what traditional distributors can offer. To grow in today s fast-paced and increasingly competitive market it is essential to be able to quickly adapt to market forces eff

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

(3R,4S)-1-(4-Fluorophenyl)-3-[(3S)-3-(4-Fluorophenyl)-3-Hydroxypropyl]-4-[4-(Phenylmethoxy)Phenyl]-2-Azetidinone

Cas:163222-32-0

Min.Order:10 Gram

FOB Price: $100.0

Type:Lab/Research institutions

inquiry

Zibo Dorne chemical technology co. LTD

Product Details Grade: pharmaceutical grade Purity:99%+ ProductionCapacity: 1000 Kilogram/Month Scope of use: For scientific research only(The product must be used legally) Our Advantage 1. Best quality with competitive price. 2. Quick shipping,

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,

Hangzhou Zhongqi chem Co.,Ltd.

Located in Hangzhou National Hi-Tech Industrial Development Zone, zhongqichem is a technical company mainly focus on the Custom synthesis, manufacturing, sales of chemicals to various industries. Benefiting from the outstanding customer service and h

Suzhou Health Chemicals Co., Ltd.

High quality,stable supply chain.Appearance:white/off-white or light yellow Storage:Store in cool and dry place, keep away from strong light and heat. Package:aluminum bottle,glass bottle,PTFE bottle,cardboard drum Application:Active Pharmaceutical I

Golden Pharma Co., Limited

GOLDEN PHARMA CO.,LIMITED.is a professional pharmaceutical company,our team have more than 20years expereince in pharmaceutical production and sales. we are a professional technical enterprise specializing in the R & D, production,QA regulation

HANGZHOU YUNUO CHEMICAL CO.,LTD

Superior quality, moderate price & quick delivery. Appearance:white crystalline powder Storage:stored in a cool, dry and ventilated place to provent sun and rain Package:25kg/drum, or as per your request. Application:Used as Pharmaceutical

GIHI CHEMICALS CO.,LIMITED

Lower price, sample is available,SDS test documents are available,large stock in warehouseAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:Fine chemical intermediates, used as the main raw material for the synthe

Wuxi TAA Chemical Industry Co.,LTD.

1.A strong technical force and advanced processing equipments. The quality of the products has been strictly inspected and all kinds of index have reached or exceeded domestic and international standards.2. Now we have established long-term stable re

Synthetic route

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
With formic acid; [(S,S)-teth-TsDpen RuCl]; triethylamine In ethylbenzene at 35 - 40℃; for 24h; Inert atmosphere;99.8%
With methanesulfonic acid; dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; methyl tertiarybutylether; toluene at -25 - -20℃; for 2.5 - 3.5h; Product distribution / selectivity;98.04%
With methanesulfonic acid; dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at -25 - -20℃; for 2.5 - 3.5h; Product distribution / selectivity;98.6%
benzyl bromide
100-39-0

benzyl bromide

ezetemibe
163222-33-1

ezetemibe

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;99%
(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

A

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

B

(3R,4S,3'R)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)-3-[3'-(4-fluorophenyl)-3'-hydroxy-propyl]-azetidin-2-one
163380-15-2

(3R,4S,3'R)-1-(4-fluorophenyl)-4-(4-hydroxyphenyl)-3-[3'-(4-fluorophenyl)-3'-hydroxy-propyl]-azetidin-2-one

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran at 22℃; for 3h;A 0.141 g
B n/a
With dimethylsulfide borane complex In tetrahydrofuran at 22℃; for 3h;
Stage #1: (3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one With sodium tetrahydroborate; chloro-trimethyl-silane; (R)-α,α-diphenylprolinol In tetrahydrofuran at 19 - 22℃; for 2.78333h; Heating / reflux;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 2℃; for 0.5h; Product distribution / selectivity;
A n/a
B n/a
With 1,1,1,3',3',3'-hexafluoro-propanol; C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; Overall yield = 99 %; enantioselective reaction;A n/a
B n/a
With C32H39BrMnN2O2P; potassium tert-butylate; hydrogen In methanol at 20℃; under 22502.3 Torr; for 16h; Glovebox; Autoclave; Optical yield = 85 percent ee; enantioselective reaction;
4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine
70627-52-0

4-benzyloxybenzylidene-N-(4-fluoro)phenylanisidine

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 64 percent / LDA; DMPU; LiCl / dimethylformamide; tetrahydrofuran / 18 h / -30 - -25 °C
2: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C
3: BF3 etherate / toluene / 0.08 h / -30 °C
4: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
5: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
6: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -5 °C
2: N,O-Bis(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / toluene / 48 h / Reflux
3: formic acid / dichloromethane / 12 h / Reflux
4: dimethyl sulfide borane / dichloromethane; toluene; tetrahydrofuran / 12 h / 15 °C
View Scheme
Multi-step reaction with 2 steps
1: N,O-bis-(trimethylsilyl)-acetamide; tetrabutyl ammonium fluoride / toluene / 60 °C
2: dimethylsulfide borane complex / dichloromethane; toluene / 3 h / -5 - 0 °C / Inert atmosphere
View Scheme
(2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde
221349-58-2

(2S,3S)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxazetidine-3-carbaldehyde

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: BF3 etherate / toluene / 0.08 h / -30 °C
2: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
3: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
4: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
(3S,4S)-4-(4-Benzyloxy-phenyl)-3-((S)-1,2-dihydroxy-ethyl)-1-(4-fluoro-phenyl)-azetidin-2-one
221349-56-0

(3S,4S)-4-(4-Benzyloxy-phenyl)-3-((S)-1,2-dihydroxy-ethyl)-1-(4-fluoro-phenyl)-azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 90 percent / NaIO4 / acetonitrile; H2O / 2 h / 20 °C
2: BF3 etherate / toluene / 0.08 h / -30 °C
3: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
4: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
5: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
lithium; 1-(4-fluoro-phenyl)-ethenolate

lithium; 1-(4-fluoro-phenyl)-ethenolate

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: BF3 etherate / toluene / 0.08 h / -30 °C
2: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
3: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
4: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
(3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[(E)-3-(4-fluoro-phenyl)-3-oxo-propenyl]-azetidin-2-one
221349-60-6

(3R,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[(E)-3-(4-fluoro-phenyl)-3-oxo-propenyl]-azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
2: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
(3S,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-hydroxy-3-oxo-propyl]-azetidin-2-one
231301-00-1

(3S,4S)-4-(4-Benzyloxy-phenyl)-1-(4-fluoro-phenyl)-3-[3-(4-fluoro-phenyl)-1-hydroxy-3-oxo-propyl]-azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 99 g / p-toluenesulfonic acid monohydrate; molecular sieves / toluene / 4 h / 40 - 50 °C
2: 71 percent / (PPh3)3RhCl; hydrogen / CH2Cl2 / 18 h / 3102.89 Torr
3: 70 percent / CBS; BH3-Me2S / toluene; CH2Cl2 / 2 h / -20 °C
View Scheme
(Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine
219653-96-0

(Z)-1-(4-(benzyloxy)phenyl)-N-(4-fluorophenyl)methaneimine

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: (nBu)3N / heptane; toluene / 80 - 90 °C
2: LiOH*H2O / methanol / 2 h
3: oxalyl chloride / CH2Cl2 / 16 h / 22 °C
4: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
5: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
View Scheme
(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone
204589-82-2

(3R,4S)-1-(4-fluorophenyl)-3-(3-hydroxy-3-oxopropyl)-4-(4-benzyloxyphenyl)-2-azetidinone

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: oxalyl chloride / CH2Cl2 / 16 h / 22 °C
2: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
3: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
View Scheme
3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride
204589-84-4

3-((3R,4S)-1-(4-fluorophenyl)-2-oxo-4-(4-(benzyloxy)phenyl)azetidin-3-yl)propionic acid chloride

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
2: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
View Scheme
methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate
204589-80-0

methyl 3-((2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl)propanoate

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: LiOH*H2O / methanol / 2 h
2: oxalyl chloride / CH2Cl2 / 16 h / 22 °C
3: (Ph3P)4Pd / tetrahydrofuran / 1 h / 10 °C
4: BH3*Me2S / tetrahydrofuran / 3 h / 22 °C
View Scheme
Multi-step reaction with 3 steps
1.1: diethyl aluminiumcholoride / toluene / -12 - 20 °C / Inert atmosphere
2.1: magnesium / tetrahydrofuran / 1 h / 40 - 50 °C / Inert atmosphere
2.2: 1 h / -5 - 0 °C
3.1: [(S,S)-teth-TsDpen RuCl]; triethylamine; formic acid / ethylbenzene / 24 h / 35 - 40 °C / Inert atmosphere
View Scheme
[14C]-Sch 57871
191330-56-0

[14C]-Sch 57871

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole
112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Stage #1: [14C]-Sch 57871; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at -20℃; for 0.0833333h;
Stage #2: With dimethylsulfide borane complex In tetrahydrofuran at -20℃; for 1.5h;
1-(4-fluorophenyl)-4(S)-(4-hydroxyphenyl)-3(R)-(3-oxo-3-phenylpropyl)-2-azetidinone
163222-31-9

1-(4-fluorophenyl)-4(S)-(4-hydroxyphenyl)-3(R)-(3-oxo-3-phenylpropyl)-2-azetidinone

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran at -20℃; for 1.5h;
methanol
67-56-1

methanol

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one
190595-65-4

(3R,4S)-4-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3-oxopropyl]azetidin-2-one

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole
112022-83-0

(3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran
1-Bromo-4-fluorobenzene
460-00-4

1-Bromo-4-fluorobenzene

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: magnesium; Bis<2-(N,N-dimethylamino)aethyl>aether / 0.5 h / 0 °C
2.1: (R)-1,1'-Bi-2-naphthol / titanium(IV) isopropylate / diethyl ether; tetrahydrofuran / 1.5 h / 0 - 25 °C
2.2: -20 - 25 °C
2.3: 0 °C
View Scheme
Multi-step reaction with 2 steps
1.1: magnesium / tetrahydrofuran / 1 h / 40 - 50 °C / Inert atmosphere
1.2: 1 h / -5 - 0 °C
2.1: [(S,S)-teth-TsDpen RuCl]; triethylamine; formic acid / ethylbenzene / 24 h / 35 - 40 °C / Inert atmosphere
View Scheme
3-[(2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]propanal
1412967-16-8

3-[(2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]propanal

4-flourophenylmagnesium bromide
352-13-6

4-flourophenylmagnesium bromide

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Stage #1: 4-flourophenylmagnesium bromide With (R)-1,1'-Bi-2-naphthol; titanium(IV) isopropylate In tetrahydrofuran; diethyl ether at 0 - 25℃; for 1.5h;
Stage #2: 3-[(2S,3R)-2-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]propanal In tetrahydrofuran; diethyl ether at -20 - 25℃;
Stage #3: With hydrogenchloride; water In tetrahydrofuran; diethyl ether at 0℃;
(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one
1412967-14-6

(3R,4S)-4-(4-(benzyloxy)phenyl)-1-(4-fluorophenyl)-3-(3-hydroxypropyl)azetidin-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydrogencarbonate; sodium hypochlorite; potassium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / Difluoromethane / 25 °C / Cooling with ice
2.1: (R)-1,1'-Bi-2-naphthol / titanium(IV) isopropylate / diethyl ether; tetrahydrofuran / 1.5 h / 0 - 25 °C
2.2: -20 - 25 °C
2.3: 0 °C
View Scheme
(1'R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one
1416263-33-6

(1'R,6R)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium hydroxide / tetrahydrofuran; water / 18 h
2: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
3: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(1'S,3R,6S)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one
1416263-36-9

(1'S,3R,6S)-3-[(4-benzyloxyphenyl)-(4-fluorophenylamino)-methyl]-6-(4-fluorophenyl)-tetrahydro-2H-pyran-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
With tert-butylmagnesium chloride In diethyl ether at 0℃; for 2h;
(3S,3aS,6S,7aS)-3-(4-(benzyloxy)phenyl)-2,6-bis(4-fluorophenyl)tetrahydro-2H-pyrano[3,4-d]isoxazol-4(6H)-one
1416263-37-0

(3S,3aS,6S,7aS)-3-(4-(benzyloxy)phenyl)-2,6-bis(4-fluorophenyl)tetrahydro-2H-pyrano[3,4-d]isoxazol-4(6H)-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
2: Burgess Reagent / toluene / 18 h / 90 °C
3: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
4: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(R)-2,3-dihydro-2-(4-fluorophenyl)-4H-pyran-4-one

(R)-2,3-dihydro-2-(4-fluorophenyl)-4H-pyran-4-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
2: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
3: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
4: toluene / 72 h / Reflux
5: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
6: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
7: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
8: Burgess Reagent / toluene / 18 h / 90 °C
9: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
10: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 10 steps
1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
2: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
3: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
4: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
5: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
6: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
7: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
8: Burgess Reagent / toluene / 18 h / 90 °C
9: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
10: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
2.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
3.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
4.1: toluene / 72 h / Reflux
5.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
6.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
6.2: 0.25 h / 20 °C
7.1: lithium hydroxide / tetrahydrofuran; water / 18 h
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
9.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
2.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
3.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
4.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
5.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
6.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
6.2: 0.25 h / 20 °C
7.1: lithium hydroxide / tetrahydrofuran; water / 18 h
8.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
9.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(3S,4S,6S)-3-((S)-(4-(benzyloxy)phenyl)(4-fluorophenylamino)methyl)-6-(4-fluorophenyl)-4-hydroxytetrahydro-2H-pyran-2-one

(3S,4S,6S)-3-((S)-(4-(benzyloxy)phenyl)(4-fluorophenylamino)methyl)-6-(4-fluorophenyl)-4-hydroxytetrahydro-2H-pyran-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Burgess Reagent / toluene / 18 h / 90 °C
2: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
3: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(6S)-3-((R)-(4-(benzyloxy)phenyl)(4-fluorophenylamino)-methyl)-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one
1416263-38-1

(6S)-3-((R)-(4-(benzyloxy)phenyl)(4-fluorophenylamino)-methyl)-6-(4-fluorophenyl)-5,6-dihydro-2H-pyran-2-one

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
2: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
4-fluorobenzaldehyde
459-57-4

4-fluorobenzaldehyde

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: [(R,R)-salen-Cr]BF4 / tert-butyl methyl ether / 24 h / -30 °C / Molecular sieve
1.2: 5 h / 20 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
3.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
4.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
5.1: toluene / 72 h / Reflux
6.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
7.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
7.2: 0.25 h / 20 °C
8.1: lithium hydroxide / tetrahydrofuran; water / 18 h
9.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
10.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 10 steps
1.1: [(R,R)-salen-Cr]BF4 / tert-butyl methyl ether / 24 h / -30 °C / Molecular sieve
1.2: 5 h / 20 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
3.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
4.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
5.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
6.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
7.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
7.2: 0.25 h / 20 °C
8.1: lithium hydroxide / tetrahydrofuran; water / 18 h
9.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
10.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 11 steps
1.1: [(R,R)-salen-Cr]BF4 / tert-butyl methyl ether / 24 h / -30 °C / Molecular sieve
1.2: 5 h / 20 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
3.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
4.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
5.1: toluene / 72 h / Reflux
6.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
8.1: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
9.1: Burgess Reagent / toluene / 18 h / 90 °C
10.1: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
11.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 11 steps
1.1: [(R,R)-salen-Cr]BF4 / tert-butyl methyl ether / 24 h / -30 °C / Molecular sieve
1.2: 5 h / 20 °C
2.1: cerium(III) chloride heptahydrate; sodium tetrahydroborate / dichloromethane; methanol / 0.5 h / -20 °C
3.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
4.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
5.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
6.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
8.1: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
9.1: Burgess Reagent / toluene / 18 h / 90 °C
10.1: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
11.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(2R)-2-(4-fluorophenyl)-3,4-dihydro-2H-pyran-4-ol
1416263-27-8

(2R)-2-(4-fluorophenyl)-3,4-dihydro-2H-pyran-4-ol

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
2.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
3.1: toluene / 72 h / Reflux
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1.1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
2.1: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
3.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
2: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
3: toluene / 72 h / Reflux
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: dihydrogen peroxide; molybdenum(VI) oxide / acetonitrile / 24 h
2: pyridine; acetic anhydride / dichloromethane / 2 h / 20 °C
3: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2.1: methanesulfonic acid / acetone / 2 h / 20 °C
3.1: toluene / 72 h / Reflux
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1.1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2.1: methanesulfonic acid / acetone / 2 h / 20 °C
3.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2: methanesulfonic acid / acetone / 2 h / 20 °C
3: toluene / 72 h / Reflux
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2: methanesulfonic acid / acetone / 2 h / 20 °C
3: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate / 12 h / 20 °C
1.2: 4 h / Reflux
2.1: N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; titanium tetrachloride / dichloromethane / 3 h / -5 °C
3.1: N,O-Bis(trimethylsilyl)acetamide; tetrabutyl ammonium fluoride / toluene / 48 h / Reflux
4.1: formic acid / dichloromethane / 12 h / Reflux
5.1: dimethyl sulfide borane / dichloromethane; toluene; tetrahydrofuran / 12 h / 15 °C
View Scheme
benzyl chloride
100-44-7

benzyl chloride

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2.1: methanesulfonic acid / acetone / 2 h / 20 °C
3.1: toluene / 72 h / Reflux
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1.1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2.1: methanesulfonic acid / acetone / 2 h / 20 °C
3.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
5.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
5.2: 0.25 h / 20 °C
6.1: lithium hydroxide / tetrahydrofuran; water / 18 h
7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
8.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2: methanesulfonic acid / acetone / 2 h / 20 °C
3: toluene / 72 h / Reflux
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: potassium carbonate; potassium iodide / tetrahydrofuran / 20 h / Reflux
2: methanesulfonic acid / acetone / 2 h / 20 °C
3: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
4: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
5: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
6: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
7: Burgess Reagent / toluene / 18 h / 90 °C
8: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
9: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
p-benzyloxybenzaldehyde
4397-53-9

p-benzyloxybenzaldehyde

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: methanesulfonic acid / acetone / 2 h / 20 °C
2.1: toluene / 72 h / Reflux
3.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
4.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
4.2: 0.25 h / 20 °C
5.1: lithium hydroxide / tetrahydrofuran; water / 18 h
6.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
7.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1.1: methanesulfonic acid / acetone / 2 h / 20 °C
2.1: scandium tris(trifluoromethanesulfonate) / toluene / 72 h / 30 °C / Molecular sieve
3.1: potassium iodide; chloro-trimethyl-silane / acetonitrile / 0.58 h / 20 °C
4.1: chloro-trimethyl-silane; 1H-imidazole / dichloromethane / 0.5 h / 20 °C
4.2: 0.25 h / 20 °C
5.1: lithium hydroxide / tetrahydrofuran; water / 18 h
6.1: triphenylphosphine; di-isopropyl azodicarboxylate / 3 h / 0 °C
7.1: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1: methanesulfonic acid / acetone / 2 h / 20 °C
2: toluene / 72 h / Reflux
3: lithium hydroxide monohydrate / tetrahydrofuran; water / 18 h
4: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 3 h / 0 °C
5: potassium iodide / acetonitrile; water / 0.58 h / 20 °C
6: Burgess Reagent / toluene / 18 h / 90 °C
7: platinum(IV) oxide; hydrogen / toluene / 20 °C / 750.08 Torr
8: tert-butylmagnesium chloride / diethyl ether / 2 h / 0 °C
View Scheme
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With 10 wt% Pd(OH)2 on carbon; hydrogen In methanol; cyclohexane at 70℃; under 760.051 Torr; for 3h;99%
With 5%-palladium/activated carbon; hydrogen In tetrahydrofuran; ethanol at 50 - 55℃; under 37.5038 - 75.0075 Torr;90.3%
With palladium 10% on activated carbon; ammonium formate; acetic acid for 6h; Reflux;90%
L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

(1S)-3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl (2S)-2-{[(tert-butoxy)carbonyl]amino}propanoate

(1S)-3-[(2S,3R)-2-[4-(benzyloxy)phenyl]-1-(4-fluorophenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl (2S)-2-{[(tert-butoxy)carbonyl]amino}propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Inert atmosphere;69%
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

1-(4-fluorophenyl)-(3R)-[(4-fluorophenyl)-(2E)-propenyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone

1-(4-fluorophenyl)-(3R)-[(4-fluorophenyl)-(2E)-propenyl]-(4S)-(4-hydroxyphenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr
2: p-TsOH*H2O / toluene / 6 h / 80 °C
View Scheme
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

4(S)-(4-acetyloxyphenyl)-3(R)-(3(S)-acetyloxy-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)-2-azetidinone
163380-20-9

4(S)-(4-acetyloxyphenyl)-3(R)-(3(S)-acetyloxy-3-(4-fluorophenyl)propyl)-1-(4-fluorophenyl)-2-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2 / 10percent Pd/C / ethanol / 16 h / 3102.9 Torr
2: 0.260 g / pyridine / CH2Cl2 / 1 h / 22 °C
View Scheme
(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone
163222-32-0

(3R,4S)-1-(4-fluorophenyl)-3-[3-(4-fluorophenyl)-3(S)-hydroxypropyl]-4-(4-benzyloxyphenyl)-2-azetidinone

A

EZT-FAM
1197811-72-5

EZT-FAM

B

ezetemibe
163222-33-1

ezetemibe

Conditions
ConditionsYield
With formic acid; ammonium formate; 5%-palladium/activated carbon In methanol at 20℃; Product distribution / selectivity; Inert atmosphere;

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