Advantage : LIDE PHARMACEUTICALS LTD. is a mid-small manufacturing-type enterprise, engaged in pharmaceutical intermediates of R&D, custom-made and production, and also involving trading chemicals for export. We have established the R&
Cas:204255-11-8
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inquirySpecification:USP/EP Month production ablity:50kg/Month Low price& High quality Manufacturer Jinlan Pharm-Drugs Technology Co.,Limited (with its export company Hangzhou Royall Import & Export Co.,Ltd.)is located in Hangzhou, Zhej
Cas:204255-11-8
Min.Order:1 Gram
FOB Price: $1.0
Type:Trading Company
inquiryWhy 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
Cas:204255-11-8
Min.Order:1 Kilogram
FOB Price: $1200.0 / 1500.0
Type:Trading Company
inquiryour company is a professional Pharmaceutical company. We are specialized in manufacturing and R&D of API & Intermediates, Contract Manufacturing, Contract Research, and International Trading business as well. *We own a R&D center
Cas:204255-11-8
Min.Order:1 Gram
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Type:Lab/Research institutions
inquiryItems Standard Result Assay 98%min ----------------------------------------------------------------------------------------------
Cas:204255-11-8
Min.Order:1 Gram
FOB Price: $100.0 / 500.0
Type:Trading Company
inquiryUnique advantages Guaranteed the purity High quality & competitive price Quality control Fast feedback Prompt shipment Appearance:Off-white powder Storage:-20°C Freezer Package:100g,1kg/foil bag Application:As medicine mate
Cas:204255-11-8
Min.Order:100 Gram
FOB Price: $6.0 / 8.0
Type:Trading Company
inquiry1.Hefei TNJ Chemical Industry Co.Limited(ISO9001:2008),are strong in the field of Pharmaceuticals,food additives,plant extract and fine chemical for more than 10 years. 2.Full experience of large numbers container loading in main Chinese seap
Cas:204255-11-8
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Type:Trading Company
inquiryOseltamivir phosphate CAS No.:204255-11-8 Name: Oseltamivir phosphate Synonyms Tamiflu; Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate phosphate Molecular Structure: Molecular Formula: C16H28
Cas:204255-11-8
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FOB Price: $2.0
Type:Other
inquiryhigh 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
Cas:204255-11-8
Min.Order:1 Kilogram
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Type:Manufacturers
inquiryThe 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
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
Cas:204255-11-8
Min.Order:1 Gram
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Type:Manufacturers
inquiryShanghai Seasonsgreen Chemical is a high-tech research and development, production, sale and custom synthesis set in one high-tech chemical products enterprises. Our sales and marketing division is located in Shanghai, serving international pharmaceu
Cas:204255-11-8
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Type:Manufacturers
inquiryDayangchem’s 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. DayangChem can provide different quantiti
Cas:204255-11-8
Min.Order:1 Gram
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Type:Lab/Research institutions
inquiry
Cas:204255-11-8
Min.Order:1 Metric Ton
FOB Price: $1.0
Type:Manufacturers
inquiryHebei yanxi chemical co., LTD is a professional research, development and production . enterprise backbone members by local well-known entrepreneurs and professional senior engineers in the party's "low carbon environmental protection
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Min.Order:1 Kilogram
FOB Price: $11.0 / 16.0
Type:Trading Company
inquiryOseltamivir phosphate Basic information Anti-influenza virus Application Product Name: Oseltamivir phosphate Synonyms: ethyl (3r,4r,5s)-4-acet
Cas:204255-11-8
Min.Order:1 Kilogram
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Type:Lab/Research institutions
inquiryOur 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
Cas:204255-11-8
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FOB Price: $9.0 / 99.0
Type:Trading Company
inquiryWITH 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
Cas:204255-11-8
Min.Order:1 Kilogram
FOB Price: $139.0 / 210.0
Type:Trading Company
inquiryOur Advantage: high quality with competitive price High quality standard: BP/USP/EP Enterprise standard All purity customized Fast and safe delivery We have reliable forwarder who can help us deliver our goods more fast and safe. We
Cas:204255-11-8
Min.Order:10 Kilogram
Negotiable
Type:Trading Company
inquiry1. Product advantages High purity, all above 98.5%, no impurities after dissolution We will test each batch to ensure quality OEM and private brand services designed for free Various cap colors available We can also provide MT1 peptide powd
Cas:204255-11-8
Min.Order:1 Kilogram
FOB Price: $50.0 / 100.0
Type:Trading Company
inquiryChemical Properties: Cas No. 204255-11-8 Storage Please store the product under the recommended conditions in the Certificate of Analysis. M.Wt
1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Powder Storage:Store in sealed conta
Cas:204255-11-8
Min.Order:10 Gram
Negotiable
Type:Other
inquiryHanways chempharm is a specialized company concentrating on the R&D, production, marketing and technical service of APIs and pharmaceutical intermediates. The marketing department is located in Wuhan. We have two GMP facilities in Hubei Pr
Cas:204255-11-8
Min.Order:1 Kilogram
FOB Price: $200.0 / 400.0
Type:Trading Company
inquiry1.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
Cas:204255-11-8
Min.Order:1 Kilogram
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Type:Lab/Research institutions
inquiryProduct Name: Oseltamivir phosphate Synonyms: Osteltamivir phosphate;(3R,5S)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate phosphate;Oseltamivir phosphat;Oseltamivir Phosphate (200 mg);Oselt;OseltaMivir Acid-D3 Phosphate
Cas:204255-11-8
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryOur company has been in existence for 10 years since its establishment. We have our own unique team. The company integrates independent research and development, production and sales. We have established famous brands at home and abroad. At present
Cas:204255-11-8
Min.Order:1 Kilogram
FOB Price: $80.0 / 100.0
Type:Trading Company
inquiryOseltamivir phosphate CAS:204255-11-8 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic in
Cas:204255-11-8
Min.Order:1 Gram
Negotiable
Type:Lab/Research institutions
inquiryHello, dear friend! I'm Hansen and Allen from China. Welcome to my lookchem mall! The following is a brief introduction of our company's products and services. If you are interested in our products, please contact us by emai
Cas:204255-11-8
Min.Order:1 Kilogram
Negotiable
Type:Lab/Research institutions
inquiry1.high quality: quality is life. quality is the most important element for all goods. we have a lab doing research in wuhan china. hplc and nmr is available if needed. 2.reasonable price: we provide high quality products wi
Cas:204255-11-8
Min.Order:10 Gram
Negotiable
Type:Lab/Research institutions
inquiryCompany information: Hebei Mojin Biotechnology Co., Ltd, Our company is a professional in carbomer,carbopol,lead acetate,meglumine diphenyl ethylamine and other chemical raw materials and chemical reagents research and development production enterpr
Cas:204255-11-8
Min.Order:1 Kilogram
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Type:Trading Company
inquiryoseltamivir
oseltamivir phosphate
Conditions | Yield |
---|---|
With phosphoric acid In ethanol at 50℃; for 0.0166667h; Sonication; | 98% |
With phosphoric acid In ethanol at -18.8℃; for 17h; | 89.9% |
With phosphoric acid In ethanol at 50 - 55℃; | 88.6% |
oseltamivir phosphate
Conditions | Yield |
---|---|
Stage #1: ethyl (3R,4R,5S)-4-N-acetylamino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate With palladium 10% on activated carbon; 2,2'-iminobis[ethanol] In ethanol at 68 - 78℃; for 8h; Stage #2: With phosphoric acid In ethanol at 45 - 55℃; Reagent/catalyst; | 96.31% |
With 1,3-dimethylbarbituric acid; phosphoric acid; palladium 10% on activated carbon; triphenylphosphine In ethanol at 55 - 78℃; Temperature; Reagent/catalyst; Large scale; | 89% |
Stage #1: ethyl (3R,4R,5S)-4-N-acetylamino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate With tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid In dichloromethane at 35℃; for 7h; Inert atmosphere; Stage #2: With phosphoric acid In ethanol at 48 - 52℃; for 2h; | 85% |
oseltamivir
oseltamivir phosphate
Conditions | Yield |
---|---|
Stage #1: oseltamivir With tributylphosphine; triphenylphosphine In ethanol; water at 50℃; for 3h; Stage #2: With phosphoric acid In ethanol | 92% |
Stage #1: oseltamivir With Lindlar's catalyst; hydrogen In ethanol at 20℃; under 760.051 Torr; for 16h; Stage #2: With phosphoric acid In ethanol; ethyl acetate at 50℃; for 0.5h; | 91% |
91% |
Conditions | Yield |
---|---|
In ethanol; water at 50 - 55℃; for 1.5 - 2h; | 88% |
(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
With phosphoric acid In ethanol at 78℃; for 12h; Inert atmosphere; | 83% |
With phosphoric acid In ethanol at 0 - 78℃; for 15h; Inert atmosphere; | 83% |
With phosphoric acid In ethanol at 50℃; for 6h; | 81% |
oseltamivir phosphate
Conditions | Yield |
---|---|
Stage #1: (3S,4S,5S)-4-acetamido-5-allyloxycarbonylamino-1-ethoxycarbonyl-3-(3-pentyloxy)cyclohex-2-ene With 1,3-dimethylbarbituric acid; 5%-palladium/activated carbon; triphenylphosphine In ethanol at 80℃; for 1h; Stage #2: With phosphoric acid In ethanol at 50℃; | 76% |
tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate
ethanol
oseltamivir phosphate
Conditions | Yield |
---|---|
Stage #1: tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate; ethanol With hydrogenchloride at 60℃; for 4h; Stage #2: With phosphoric acid at 4 - 50℃; | 50% |
Stage #1: tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate; ethanol With hydrogenchloride Stage #2: With sodium hydroxide Stage #3: With phosphoric acid |
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: LiOH 1.2: NEt3 2.1: isobutyric anhydride; DMSO 3.1: Ni(cod)2; 1,5-cyclooctadiene 3.2: NBS; NEt3 4.1: LiAl(Ot-Bu)3H 5.1: DEAD; PPh3 5.2: 56 percent / BF3*OEt2 6.1: HCl 6.2: aq. NaOH 6.3: H3PO4 View Scheme |
(1S,2R)-2-(acetylamino)-1-(tert-butoxycarbonylamino)-4-cyclohexen-3-one
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: Ni(cod)2; 1,5-cyclooctadiene 1.2: NBS; NEt3 2.1: LiAl(Ot-Bu)3H 3.1: DEAD; PPh3 3.2: 56 percent / BF3*OEt2 4.1: HCl 4.2: aq. NaOH 4.3: H3PO4 View Scheme |
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: isobutyric anhydride; DMSO 2.1: Ni(cod)2; 1,5-cyclooctadiene 2.2: NBS; NEt3 3.1: LiAl(Ot-Bu)3H 4.1: DEAD; PPh3 4.2: 56 percent / BF3*OEt2 5.1: HCl 5.2: aq. NaOH 5.3: H3PO4 View Scheme |
tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: DEAD; PPh3 1.2: 56 percent / BF3*OEt2 2.1: HCl 2.2: aq. NaOH 2.3: H3PO4 View Scheme |
(6-acetylamino-3-cyano-5-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: LiAl(Ot-Bu)3H 2.1: DEAD; PPh3 2.2: 56 percent / BF3*OEt2 3.1: HCl 3.2: aq. NaOH 3.3: H3PO4 View Scheme |
ethyl (3R,4R,5S)-4-amino-5-azido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.98 kg / sodium bicarbonate / hexane / 1 h 2: 1.) hydrogen, 2.) phophoric acid / 1.) Raney nickel / 1.) ethanol, 16 h, 2.) ethanol, 55 65 deg C View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C 2: hydrogen / ethanol / 18 h / 760.05 Torr 3: phosphoric acid / acetone; ethanol / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: pyridine / 1 h / 20 °C 2: hydrogen / ethanol / 10 h 3: phosphoric acid / ethanol / 3 h / 60 °C View Scheme |
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) sodium azide, ammonium chloride, 2.) trimethylphosphine / 1.) ethanol, water, 70-75 deg C, 18 h, 2.) acetonitrile, <38 deg C, 2 h 2: sodium azide, ammonium chloride / dimethylformamide / 18 h / 70 - 80 °C 3: 0.98 kg / sodium bicarbonate / hexane / 1 h 4: 1.) hydrogen, 2.) phophoric acid / 1.) Raney nickel / 1.) ethanol, 16 h, 2.) ethanol, 55 65 deg C View Scheme | |
Multi-step reaction with 6 steps 1.1: boron trifluoride diethyl etherate / 1.17 h / 0 °C 1.2: 4 h / 0 - 20 °C 1.3: 36 h / 20 °C 2.1: triethylamine; dmap / 1 h / 0 °C 3.1: sodium hydride / dichloromethane; dimethyl sulfoxide; mineral oil / 8 h / 20 °C 4.1: boron trifluoride diethyl etherate / dichloromethane / 0.37 h / -15 °C 5.1: caesium carbonate / dimethyl sulfoxide / 0.25 h / 80 °C 5.2: 0.33 h / 80 °C 6.1: phosphoric acid / ethyl acetate; ethanol / 2 h / 50 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: sodium azide; ammonium chloride / water; ethanol / 8 h / 70 - 75 °C 1.2: 6 h / Reflux 2.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 5 h / 8 - 85 °C 3.1: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C 4.1: hydrogen / ethanol / 18 h / 760.05 Torr 5.1: phosphoric acid / acetone; ethanol / Reflux View Scheme |
ethyl-(1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium azide, ammonium chloride / dimethylformamide / 18 h / 70 - 80 °C 2: 0.98 kg / sodium bicarbonate / hexane / 1 h 3: 1.) hydrogen, 2.) phophoric acid / 1.) Raney nickel / 1.) ethanol, 16 h, 2.) ethanol, 55 65 deg C View Scheme | |
Multi-step reaction with 4 steps 1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 5 h / 8 - 85 °C 2: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C 3: hydrogen / ethanol / 18 h / 760.05 Torr 4: phosphoric acid / acetone; ethanol / Reflux View Scheme |
ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 95 percent / perchloric acid 2: 1.) BH3-SMe2, trimethylsilyl trifluoromethanesulfonate, 2.) potassium hydroden carbonate / 1.) dichloromethane, -20 - -10 deg C, 0.2 h, 2.) ethanol, water, 55-65 deg C, 1 h 3: 1.) sodium azide, ammonium chloride, 2.) trimethylphosphine / 1.) ethanol, water, 70-75 deg C, 18 h, 2.) acetonitrile, <38 deg C, 2 h 4: sodium azide, ammonium chloride / dimethylformamide / 18 h / 70 - 80 °C 5: 0.98 kg / sodium bicarbonate / hexane / 1 h 6: 1.) hydrogen, 2.) phophoric acid / 1.) Raney nickel / 1.) ethanol, 16 h, 2.) ethanol, 55 65 deg C View Scheme | |
Multi-step reaction with 7 steps 1.1: perchloric acid / 18 h 2.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 2.2: 12 h / 20 °C 2.3: 2 h / 55 - 65 °C 3.1: sodium azide; ammonium chloride / water; ethanol / 8 h / 70 - 75 °C 3.2: 6 h / Reflux 4.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 5 h / 8 - 85 °C 5.1: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C 6.1: hydrogen / ethanol / 18 h / 760.05 Torr 7.1: phosphoric acid / acetone; ethanol / Reflux View Scheme |
ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 1.) BH3-SMe2, trimethylsilyl trifluoromethanesulfonate, 2.) potassium hydroden carbonate / 1.) dichloromethane, -20 - -10 deg C, 0.2 h, 2.) ethanol, water, 55-65 deg C, 1 h 2: 1.) sodium azide, ammonium chloride, 2.) trimethylphosphine / 1.) ethanol, water, 70-75 deg C, 18 h, 2.) acetonitrile, <38 deg C, 2 h 3: sodium azide, ammonium chloride / dimethylformamide / 18 h / 70 - 80 °C 4: 0.98 kg / sodium bicarbonate / hexane / 1 h 5: 1.) hydrogen, 2.) phophoric acid / 1.) Raney nickel / 1.) ethanol, 16 h, 2.) ethanol, 55 65 deg C View Scheme | |
Multi-step reaction with 6 steps 1.1: dimethylsulfide borane complex; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -30 - -20 °C 1.2: 12 h / 20 °C 1.3: 2 h / 55 - 65 °C 2.1: sodium azide; ammonium chloride / water; ethanol / 8 h / 70 - 75 °C 2.2: 6 h / Reflux 3.1: sodium azide; ammonium chloride / N,N-dimethyl-formamide / 5 h / 8 - 85 °C 4.1: sodium hydrogencarbonate / water; dichloromethane / 1 h / 20 °C 5.1: hydrogen / ethanol / 18 h / 760.05 Torr 6.1: phosphoric acid / acetone; ethanol / Reflux View Scheme | |
Multi-step reaction with 4 steps 1.1: caesium carbonate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C 2.1: triethylsilane; titanium tetrachloride / dichloromethane / 2 h / -40 - -35 °C / Inert atmosphere 3.1: acetic acid; sulfuric acid / 1 h / 0 - 20 °C 4.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 7 h / 35 °C / Inert atmosphere 4.2: 2 h / 48 - 52 °C View Scheme |
(3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester
phosphoric acid
oseltamivir phosphate
Conditions | Yield |
---|---|
With sodium hydroxide; hydrogen bromide; acetic anhydride; acetic acid; triethylamine; cobalt In ethanol; ethyl acetate; acetone |
oseltamivir phosphate
Conditions | Yield |
---|---|
With phosphoric acid In ethanol; acetone at 25 - 30℃; for 1.5h; |
(1S,5S,6R)-ethyl 7-acetyl-5-(tert-butoxycarbonylamino)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate
2-pentanol
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 2.2: 4 °C View Scheme |
(1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Reflux 2.1: potassium carbonate / 5 h / 20 °C 3.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 6.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 6.2: 1 h 7.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 8.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 8.2: 0.5 h / -78 °C / Inert atmosphere 8.3: 0.5 h 9.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 10.1: triphenylphosphine / toluene / 3 h / Reflux 11.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 12.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 13.2: 4 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Reflux 2.1: potassium carbonate / 5 h / 20 °C 3.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 6.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 6.2: 1 h 7.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 8.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 8.2: 0.5 h / -78 °C / Inert atmosphere 8.3: 0.5 h 9.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 9.2: 3 h / Reflux 10.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 11.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 12.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 12.2: 4 °C View Scheme | |
Multi-step reaction with 13 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Reflux 2.1: potassium carbonate / 5 h / 20 °C 3.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 6.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 6.2: 1 h 7.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 8.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 8.2: 0.5 h / -78 °C / Inert atmosphere 8.3: 0.5 h 9.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 9.2: 24 h / 20 °C 10.1: triphenylphosphine / toluene / 3 h / Reflux 11.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 12.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 13.2: 4 °C View Scheme | |
Multi-step reaction with 13 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Reflux 2.1: potassium carbonate / 5 h / 20 °C 3.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 6.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 6.2: 1 h 7.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 8.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 8.2: 0.5 h / -78 °C / Inert atmosphere 8.3: 0.5 h 9.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 9.2: 3 h / Reflux 10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / 20 °C 11.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 12.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 13.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 13.2: 4 °C View Scheme |
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 2.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3.2: 4 °C View Scheme |
(1R,5R)-ethyl 5-hydroxycyclohex-3-enecarboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 4.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 4.2: 1 h 5.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 6.2: 0.5 h / -78 °C / Inert atmosphere 6.3: 0.5 h 7.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 8.1: triphenylphosphine / toluene / 3 h / Reflux 9.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 10.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 11.2: 4 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 4.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 4.2: 1 h 5.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 6.2: 0.5 h / -78 °C / Inert atmosphere 6.3: 0.5 h 7.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 7.2: 3 h / Reflux 8.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 9.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 10.2: 4 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 4.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 4.2: 1 h 5.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 6.2: 0.5 h / -78 °C / Inert atmosphere 6.3: 0.5 h 7.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 7.2: 24 h / 20 °C 8.1: triphenylphosphine / toluene / 3 h / Reflux 9.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 10.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 11.2: 4 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 °C / Inert atmosphere 2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 4.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 4.2: 1 h 5.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 6.2: 0.5 h / -78 °C / Inert atmosphere 6.3: 0.5 h 7.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 7.2: 3 h / Reflux 8.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / 20 °C 9.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 10.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 11.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 11.2: 4 °C View Scheme |
(1R,5S)-ethyl 5-(N-(tert-butoxycarbonyl)-4-nitrophenylsulfonamido)cyclohex-3-enecarboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 3.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 3.2: 1 h 4.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 5.2: 0.5 h / -78 °C / Inert atmosphere 5.3: 0.5 h 6.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 7.1: triphenylphosphine / toluene / 3 h / Reflux 8.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 9.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 10.2: 4 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 3.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 3.2: 1 h 4.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 5.2: 0.5 h / -78 °C / Inert atmosphere 5.3: 0.5 h 6.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 6.2: 3 h / Reflux 7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / 20 °C 8.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 9.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 10.2: 4 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 3.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 3.2: 1 h 4.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 5.2: 0.5 h / -78 °C / Inert atmosphere 5.3: 0.5 h 6.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 6.2: 24 h / 20 °C 7.1: triphenylphosphine / toluene / 3 h / Reflux 8.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 9.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 10.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 10.2: 4 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 3.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 3.2: 1 h 4.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 5.2: 0.5 h / -78 °C / Inert atmosphere 5.3: 0.5 h 6.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 6.2: 3 h / Reflux 7.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 8.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 9.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 9.2: 4 °C View Scheme |
ethyl (5S)-5-((tert-butoxycarbonyl)amino)cyclohex-3-ene-1-carboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 2.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 2.2: 1 h 3.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 4.2: 0.5 h / -78 °C / Inert atmosphere 4.3: 0.5 h 5.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 6.1: triphenylphosphine / toluene / 3 h / Reflux 7.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 8.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 9.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 9.2: 4 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 2.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 2.2: 1 h 3.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 4.2: 0.5 h / -78 °C / Inert atmosphere 4.3: 0.5 h 5.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 5.2: 3 h / Reflux 6.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 7.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 8.2: 4 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 2.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 2.2: 1 h 3.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 4.2: 0.5 h / -78 °C / Inert atmosphere 4.3: 0.5 h 5.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 5.2: 24 h / 20 °C 6.1: triphenylphosphine / toluene / 3 h / Reflux 7.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 8.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 9.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 9.2: 4 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 °C 2.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 2.2: 1 h 3.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 4.2: 0.5 h / -78 °C / Inert atmosphere 4.3: 0.5 h 5.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 5.2: 3 h / Reflux 6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / 20 °C 7.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 8.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 9.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 9.2: 4 °C View Scheme |
(1R,3S,5S,6S)-ethyl 5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptane-3-carboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 1.2: 1 h 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 3.3: 0.5 h 4.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 5.1: triphenylphosphine / toluene / 3 h / Reflux 6.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 7.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 8.2: 4 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 1.2: 1 h 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 3.3: 0.5 h 4.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 4.2: 3 h / Reflux 5.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 6.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 7.2: 4 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 1.2: 1 h 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 3.3: 0.5 h 4.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 4.2: 24 h / 20 °C 5.1: triphenylphosphine / toluene / 3 h / Reflux 6.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 7.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 8.2: 4 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 °C / Inert atmosphere 1.2: 1 h 2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 3.3: 0.5 h 4.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 4.2: 3 h / Reflux 5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / 20 °C 6.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 7.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 8.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 8.2: 4 °C View Scheme |
(1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 °C / Inert atmosphere 2.3: 0.5 h 3.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 4.1: triphenylphosphine / toluene / 3 h / Reflux 5.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 6.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 7.2: 4 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 °C / Inert atmosphere 2.3: 0.5 h 3.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 3.2: 24 h / 20 °C 4.1: triphenylphosphine / toluene / 3 h / Reflux 5.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 6.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 7.2: 4 °C View Scheme |
(1S,3S,4S,5S)-ethyl 3-azido-5-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 °C / Inert atmosphere 2.3: 0.5 h 3.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 3.2: 3 h / Reflux 4.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 5.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6.2: 4 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 2.2: 0.5 h / -78 °C / Inert atmosphere 2.3: 0.5 h 3.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 3.2: 3 h / Reflux 4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 24 h / 20 °C 5.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 6.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 7.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 7.2: 4 °C View Scheme |
(1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-(trimethylsilyloxy)cyclohexanecarboxylate
oseltamivir phosphate
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 1.3: 0.5 h 2.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 3.1: triphenylphosphine / toluene / 3 h / Reflux 4.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 5.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6.2: 4 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere 1.2: 0.5 h / -78 °C / Inert atmosphere 1.3: 0.5 h 2.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 2.2: 24 h / 20 °C 3.1: triphenylphosphine / toluene / 3 h / Reflux 4.1: dmap; triethylamine / dichloromethane / 0 - 20 °C 5.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 6.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 6.2: 4 °C View Scheme |
oseltamivir phosphate
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 20℃; for 0.5h; | 100% |
With sodium hydroxide In water at 20℃; for 4h; | 96% |
Stage #1: oseltamivir phosphate With sodium hydroxide In 1,4-dioxane; water at 20℃; for 24h; Inert atmosphere; Stage #2: In 1,4-dioxane; water Inert atmosphere; | 88% |
oseltamivir phosphate
oseltamivir
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In water at 20℃; for 0.0833333h; Inert atmosphere; | 98% |
Stage #1: oseltamivir phosphate In dichloromethane; water at 25 - 30℃; for 0.166667h; Stage #2: With ammonia In dichloromethane; water pH=9 - 10; Stage #3: In n-heptane at 25 - 30℃; for 1h; Purification / work up; | |
Stage #1: oseltamivir phosphate In dichloromethane; water at 25 - 30℃; for 0.166667h; Stage #2: With ammonia In dichloromethane; water pH=9 - 10; Stage #3: In n-heptane; toluene at 20 - 30℃; for 3.5h; Purification / work up; | |
In dichloromethane; water at 20℃; for 0.75h; |
di-tert-butyl dicarbonate
oseltamivir phosphate
(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
Conditions | Yield |
---|---|
Stage #1: oseltamivir phosphate With sodium hydrogencarbonate In water Stage #2: di-tert-butyl dicarbonate With triethylamine | 98% |
Alkaline conditions; | 98% |
With triethylamine In methanol at 20℃; for 12h; | 96.3% |
N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine
oseltamivir phosphate
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; for 18h; | 98% |
With amine In tetrahydrofuran |
tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate
oseltamivir phosphate
(3R,4R,5S)-5-[[(1Z)-[[(tert-butoxy)carbonyl]amino]([[(tert-butoxy)carbonyl]imino])methyl]amino]-4-acetylamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃; | 98% |
tert-butyldicarbonate
oseltamivir phosphate
(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
Conditions | Yield |
---|---|
With triethylamine In methanol at 20℃; for 12h; | 96.3% |
acetic anhydride
oseltamivir phosphate
(3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: oseltamivir phosphate With dmap; triethylamine In dichloromethane Stage #2: acetic anhydride In dichloromethane | 94% |
oseltamivir phosphate
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In ethanol at 20℃; | 89% |
oseltamivir phosphate
Conditions | Yield |
---|---|
In ethanol; water at 65 - 75℃; for 8h; | 86.9% |
propionic acid
oseltamivir phosphate
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; | 86% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 60℃; for 1h; | 86% |
4-diphenylsulfonyl chloride
oseltamivir phosphate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 6h; | 85% |
With triethylamine In dichloromethane at 25 - 30℃; for 8h; | 84.7% |
4-Phenylbenzaldehyde
oseltamivir phosphate
Conditions | Yield |
---|---|
With sodium cyanoborohydride In ethanol at 20℃; for 6h; | 84% |
Stage #1: 4-Phenylbenzaldehyde; oseltamivir phosphate In ethanol at 20℃; for 0.0833333h; Stage #2: With sodium cyanoborohydride In ethanol at 20℃; for 4h; | 67% |
With sodium cyanoborohydride In ethanol at 20℃; for 6h; |
(4-biphenylyl)acetic acid
oseltamivir phosphate
Conditions | Yield |
---|---|
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 30℃; for 8h; | 82.6% |
p-toluenesulfonyl chloride
oseltamivir phosphate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 6h; | 80% |
oseltamivir phosphate
3-Phenylpropionic acid
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; | 79% |
oseltamivir phosphate
3-(chloromethyl)-5-(4-chlorophenyl)-1,2,4-oxadiazole
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 12h; | 79% |
5-(3,4-Dimethoxyphenyl)-2-furaldehyde
oseltamivir phosphate
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride In ethanol at 20℃; | 79% |
benzenesulfonyl chloride
oseltamivir phosphate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 6h; | 79% |
4-(Methylthio)benzaldehyde
oseltamivir phosphate
Conditions | Yield |
---|---|
With sodium cyanoborohydride In ethanol at 20℃; for 6h; | 77.3% |
3-thiophene carboxaldehyde
oseltamivir phosphate
Conditions | Yield |
---|---|
With sodium cyanoborohydride In methanol; ethanol at 20℃; for 6h; | 77% |
With sodium cyanoborohydride In ethanol at 20℃; for 6h; |
4-nitrobenzaldehdye
oseltamivir phosphate
Conditions | Yield |
---|---|
With sodium cyanoborohydride In methanol; ethanol at 20℃; for 6h; | 77% |
With sodium cyanoborohydride In ethanol at 30℃; for 5h; | 76.3% |
phenylacetic acid
oseltamivir phosphate
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; | 77% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 60℃; for 24h; | 77% |
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