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LIDE PHARMACEUTICALS LIMITED

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&amp

Oseltamivir phosphate/ LIDE PHARMA- Factory supply / Best price

Cas:204255-11-8

Min.Order:0

Negotiable

Type:Lab/Research institutions

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Hangzhou JINLAN Pharm-Drugs Technology Co., Ltd

Specification: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

Oseltamivir phosphate CAS 204255-11-8

Cas:204255-11-8

Min.Order:1 Gram

FOB Price: $1.0

Type:Trading Company

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Sinoway Industrial Co., Ltd.

Why is SINOWAY: 1) Specialized in pharmaceutical and healthcare industrial for 34 years. 2) ISO 9001:2015 & SGS audited supplier . 3) Accept various payment terms : T.T 30-60 days. 4) We have warehouse in USA with quickly shipment . 5) We c

Factory price 99%min Oseltamivir phosphate powder

Cas:204255-11-8

Min.Order:1 Kilogram

FOB Price: $1200.0 / 1500.0

Type:Trading Company

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Hangzhou Hysen Pharma co.,Ltd.

our 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

Oseltamivir phosphate CAS:204255-11-8

Cas:204255-11-8

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Hangzhou Dingyan Chem Co., Ltd

Items Standard Result Assay 98%min ----------------------------------------------------------------------------------------------

High purity Various Specifications Oseltamivir phosphate CAS:204255-11-8

Cas:204255-11-8

Min.Order:1 Gram

FOB Price: $100.0 / 500.0

Type:Trading Company

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Wuhan Fortuna Chemical Co.,Ltd

Unique 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

High quality Oseltamivir phosphate Cas 204255-11-8 with factory price

Cas:204255-11-8

Min.Order:100 Gram

FOB Price: $6.0 / 8.0

Type:Trading Company

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Hefei TNJ chemical industry co.,ltd

1.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

Oseltamivir phosphate

Cas:204255-11-8

Min.Order:200 Kilogram

Negotiable

Type:Trading Company

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Hangzhou Think Chemical Co. Ltd

Oseltamivir 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

High purity Oseltamivir phosphate CAS No.:204255-11-8

Cas:204255-11-8

Min.Order:1 Kilogram

FOB Price: $2.0

Type:Other

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Henan Allgreen Chemical Co.,Ltd

high quality Appearance:White or off-white Solid Storage:Sealed, dry, microtherm , avoid light and smell. Package:According to the demand of customer Application:Organic synthesis Transportation:by air or by sea Port:shanghai

Oseltamivir Phosphate (200 mg)

Cas:204255-11-8

Min.Order:1 Kilogram

Negotiable

Type:Manufacturers

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Ality Chemical Corporation

The above product is Ality Chemical's strong item with best price, good quality and fast supply. Ality Chemical has been focusing on the research and production of this field for over 14 years. At the same time, we are always committed to providi

Factory Supply Oseltramivir Phosphate

Cas:204255-11-8

Min.Order:1

Negotiable

Type:Other

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Xi'an Xszo Chem Co., Ltd.

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

High Quality 99% Oseltamivir phosphate 204255-11-8 ISO Producer

Cas:204255-11-8

Min.Order:1 Gram

FOB Price: $0.1

Type:Manufacturers

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Shanghai Seasonsgreen Chemical Co.,Ltd

Shanghai Seasonsgreen Chemical is a high-tech research and development, production, sale and custom synthesis set in one high-tech chemical products enterprises. Our sales and marketing division is located in Shanghai, serving international pharmaceu

lower price High quality Oseltamivir phosphate

Cas:204255-11-8

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Manufacturers

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Dayang Chem (Hangzhou) Co.,Ltd.

Dayangchem’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

Oseltamivir phosphate

Cas:204255-11-8

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Chemwill Asia Co., Ltd.

CHemwill -- Oseltamivir phosphate

Cas:204255-11-8

Min.Order:1 Metric Ton

FOB Price: $1.0

Type:Manufacturers

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Hebei yanxi chemical co.,LTD.

Hebei 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

Oseltamivir phosphate

Cas:204255-11-8

Min.Order:1 Kilogram

FOB Price: $11.0 / 16.0

Type:Trading Company

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Henan Tianfu Chemical Co., Ltd.

Oseltamivir phosphate Basic information Anti-influenza virus Application Product Name: Oseltamivir phosphate Synonyms: ethyl (3r,4r,5s)-4-acet

OseltaMivir Phosphate

Cas:204255-11-8

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Hebei Nengqian Chemical Import and Export Co., LTD

Our 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

Oseltamivir phosphate

Cas:204255-11-8

Min.Order:1 Kilogram

FOB Price: $9.0 / 99.0

Type:Trading Company

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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

Pharmaceutical Grade CAS 204255-11-8 with competitive price

Cas:204255-11-8

Min.Order:1 Kilogram

FOB Price: $139.0 / 210.0

Type:Trading Company

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Wuhan Han Sheng New Material Technology Co.,Ltd

Our 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

Factory direct supply Oseltamivir phosphate CAS:204255-11-8

Cas:204255-11-8

Min.Order:10 Kilogram

Negotiable

Type:Trading Company

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Hebei Sankai Chemical Technology Co., Ltd

1. 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

Oseltamivir phosphate

Cas:204255-11-8

Min.Order:1 Kilogram

FOB Price: $50.0 / 100.0

Type:Trading Company

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Henan Sinotech Import&Export Corporation

Chemical Properties: Cas No. 204255-11-8 Storage Please store the product under the recommended conditions in the Certificate of Analysis. M.Wt

Oseltamivir phosphate

Cas:204255-11-8

Min.Order:1 Kilogram

FOB Price: $1.0

Type:Other

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Hubei Langyou International Trading Co., Ltd

1. Guaranteed purity; 2. Large quantity in stock; 3. Largest manufacturer; 4. Best service after shipment with email; 5. High quality & competitive price; Appearance:White Crystalline Powder Storage:Store in sealed conta

high quality204255-11-8 Oseltamivir phosphate with best price

Cas:204255-11-8

Min.Order:10 Gram

Negotiable

Type:Other

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HANWAYS CHEMPHARM CO.,LIMITED

Hanways 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

API Raw Material GMP High Quality Antibiotic Oseltamivir Phosphate CAS: 204255-11-8 with Wholesale Price

Cas:204255-11-8

Min.Order:1 Kilogram

FOB Price: $200.0 / 400.0

Type:Trading Company

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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

Oseltamivir phosphate 204255-11-8

Cas:204255-11-8

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Shanghai Minstar Chemical Co., Ltd

Product 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

Oseltamivir phosphate

Cas:204255-11-8

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Baoji Guokang Healthchem co.,ltd

Our 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

Oseltamivir phosphate

Cas:204255-11-8

Min.Order:1 Kilogram

FOB Price: $80.0 / 100.0

Type:Trading Company

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Qingdao Beluga Import and Export Co., LTD

Oseltamivir 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

Oseltamivir phosphate CAS:204255-11-8

Cas:204255-11-8

Min.Order:1 Gram

Negotiable

Type:Lab/Research institutions

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Shandong Hanjiang Chemical Co., Ltd.

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

Oseltamivir phosphate

Cas:204255-11-8

Min.Order:1 Kilogram

Negotiable

Type:Lab/Research institutions

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Wuhan Wonda Pharm Limited

1.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

Pharma Grade Product Oseltamivir Phosphate// Oselt with good price

Cas:204255-11-8

Min.Order:10 Gram

Negotiable

Type:Lab/Research institutions

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Hebei Mojin Biotechnology Co.,Ltd

Company 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

Best Price Oseltamivir Phosphate CAS 204255-11-8

Cas:204255-11-8

Min.Order:1 Kilogram

FOB Price: $8.0 / 10.0

Type:Trading Company

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Synthetic route

oseltamivir
196618-13-0

oseltamivir

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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%
ethyl (3R,4R,5S)-4-N-acetylamino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

ethyl (3R,4R,5S)-4-N-acetylamino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
204255-06-1

oseltamivir

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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%
phosphoric acid
86119-84-8, 7664-38-2

phosphoric acid

oseltamivir
196618-13-0

oseltamivir

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
367252-68-4

(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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%
(3R,4R,5S)-4-acetamido-5-allyloxycarbonylamino-1-ethoxycarbonyl-3-(3-pentyloxy)cyclohex-1-ene

(3R,4R,5S)-4-acetamido-5-allyloxycarbonylamino-1-ethoxycarbonyl-3-(3-pentyloxy)cyclohex-1-ene

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
891831-22-4

tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate

ethanol
64-17-5

ethanol

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
(2-oxo-2,3,3aβ,4α,5,7aβ-hexahydro-benzoxazol-4-yl)-carbamic acid tert-butyl ester

(2-oxo-2,3,3aβ,4α,5,7aβ-hexahydro-benzoxazol-4-yl)-carbamic acid tert-butyl ester

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
930275-48-2

(1S,2R)-2-(acetylamino)-1-(tert-butoxycarbonylamino)-4-cyclohexen-3-one

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
(6-acetylamino-5-hydroxy-cyclohex-3-enyl)-carbamic acid tert-butyl ester

(6-acetylamino-5-hydroxy-cyclohex-3-enyl)-carbamic acid tert-butyl ester

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
927395-71-9

tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
930275-47-1

(6-acetylamino-3-cyano-5-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
204255-04-9

ethyl (3R,4R,5S)-4-amino-5-azido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
204254-96-6

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
204255-02-7

ethyl-(1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
204254-84-2

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
204254-90-0

ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methanesulfonyloxy-3a,6,7,7a-tetrahydrobenzo[1,3]dioxole-5-carboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
367252-67-3

(3R,4R,5S)-4-azido-5-tert-butoxycarbonylamino-3-(1-ethylpropoxy)cyclohex-1-enecarboxylic acid ethyl ester

phosphoric acid
86119-84-8, 7664-38-2

phosphoric acid

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
With sodium hydroxide; hydrogen bromide; acetic anhydride; acetic acid; triethylamine; cobalt In ethanol; ethyl acetate; acetone
ethyl (3R,4R,5S)-4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate tartrate

ethyl (3R,4R,5S)-4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate tartrate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
891862-23-0

(1S,5S,6R)-ethyl 7-acetyl-5-(tert-butoxycarbonylamino)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate

2-pentanol
584-02-1

2-pentanol

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
119719-61-8

(1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
(1S,5S,6R)-ethyl 5-(tert-butoxycarbonylamino)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate

(1S,5S,6R)-ethyl 5-(tert-butoxycarbonylamino)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
1287204-65-2

(1R,5R)-ethyl 5-hydroxycyclohex-3-enecarboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
1287204-66-3

(1R,5S)-ethyl 5-(N-(tert-butoxycarbonyl)-4-nitrophenylsulfonamido)cyclohex-3-enecarboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
1287204-67-4

ethyl (5S)-5-((tert-butoxycarbonyl)amino)cyclohex-3-ene-1-carboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
1287204-68-5

(1R,3S,5S,6S)-ethyl 5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptane-3-carboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
1287204-69-6

(1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-hydroxycyclohexanecarboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
1287204-70-9

(1S,3S,4S,5S)-ethyl 3-azido-5-(tert-butoxycarbonylamino)-4-hydroxycyclohexanecarboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
1287204-71-0

(1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-(trimethylsilyloxy)cyclohexanecarboxylate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
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
204255-11-8

oseltamivir phosphate

oseltamivir acid

oseltamivir acid

Conditions
ConditionsYield
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
204255-11-8

oseltamivir phosphate

oseltamivir
196618-13-0

oseltamivir

Conditions
ConditionsYield
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
24424-99-5

di-tert-butyl dicarbonate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
367252-68-4

(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Conditions
ConditionsYield
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
152120-54-2, 862686-58-6, 1143572-00-2

N,N'-bis( tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

ethyl (3R,4R,5S)-4-acetamido-5-[N2,N3-bis(tert-butoxycarbonyl)guanidino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

ethyl (3R,4R,5S)-4-acetamido-5-[N2,N3-bis(tert-butoxycarbonyl)guanidino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃; for 18h;98%
With amine In tetrahydrofuran
tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate
145013-05-4

tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate

oseltamivir phosphate
204255-11-8

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
208720-81-4

(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
ConditionsYield
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃;98%
tert-butyldicarbonate
34619-03-9

tert-butyldicarbonate

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
367252-68-4

(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 12h;96.3%
acetic anhydride
108-24-7

acetic anhydride

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

(3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester
1191921-01-3

(3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
Stage #1: oseltamivir phosphate With dmap; triethylamine In dichloromethane
Stage #2: acetic anhydride In dichloromethane
94%
5-(3,5-difluorophenyl)furan-2-carbaldehyde

5-(3,5-difluorophenyl)furan-2-carbaldehyde

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

ethyl (3R,4R,5S)-4-acetamido-5-(((5-(3,5-difluorophenyl)furan-2-yl)methyl)amino)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

ethyl (3R,4R,5S)-4-acetamido-5-(((5-(3,5-difluorophenyl)furan-2-yl)methyl)amino)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In ethanol at 20℃;89%
oseltamivir phosphate
204255-11-8

oseltamivir phosphate

C16H28N2O4*H3O4P

C16H28N2O4*H3O4P

Conditions
ConditionsYield
In ethanol; water at 65 - 75℃; for 8h;86.9%
propionic acid
802294-64-0

propionic acid

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

(3R,4R,5S)-ethyl 4-acetamido-5-(propionamido)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

(3R,4R,5S)-ethyl 4-acetamido-5-(propionamido)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;86%
(phenylthio)acetic acid chloride
7031-27-8

(phenylthio)acetic acid chloride

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

C24H34N2O6S

C24H34N2O6S

Conditions
ConditionsYield
With dihydrogen peroxide In acetonitrile at 60℃; for 1h;86%
4-diphenylsulfonyl chloride
1623-93-4

4-diphenylsulfonyl chloride

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

(3R,4R,5S)-5-(([1,1'-biphenyl]-4-sulfonamide))-4-acetamido-3-((pentan-3-yl)oxy)cyclohexene-1-ene-1-carboxylic acid ethyl ester

(3R,4R,5S)-5-(([1,1'-biphenyl]-4-sulfonamide))-4-acetamido-3-((pentan-3-yl)oxy)cyclohexene-1-ene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 6h;85%
With triethylamine In dichloromethane at 25 - 30℃; for 8h;84.7%
4-Phenylbenzaldehyde
3218-36-8

4-Phenylbenzaldehyde

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

(3R,4R,5S)-4-acetylamino-5-(([1,1'-biphenyl]-4-ylmethyl)amino)-3-(1-ethylpropyloxy)-1-cyclohexene-1-carboxylic acid ethyl ester

(3R,4R,5S)-4-acetylamino-5-(([1,1'-biphenyl]-4-ylmethyl)amino)-3-(1-ethylpropyloxy)-1-cyclohexene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
5728-52-9

(4-biphenylyl)acetic acid

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

(3R,4R,5S)-5-(2-([1,1'-biphenyl]-4-yl)acetamido)-4-acetamido-3-((pentan-3-yl)oxy)cyclohexene-1-ene-1-carboxylic acid ethyl ester

(3R,4R,5S)-5-(2-([1,1'-biphenyl]-4-yl)acetamido)-4-acetamido-3-((pentan-3-yl)oxy)cyclohexene-1-ene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
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
98-59-9

p-toluenesulfonyl chloride

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

ethyl (3R,4R,5S)-4-acetamido-5-((4-methylphenyl)sulfonamido)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

ethyl (3R,4R,5S)-4-acetamido-5-((4-methylphenyl)sulfonamido)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 6h;80%
oseltamivir phosphate
204255-11-8

oseltamivir phosphate

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

(3R,4R,5S)-ethyl 4-acetamido-5-(3-phenylpropionamido)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

(3R,4R,5S)-ethyl 4-acetamido-5-(3-phenylpropionamido)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;79%
oseltamivir phosphate
204255-11-8

oseltamivir phosphate

3-(chloromethyl)-5-(4-chlorophenyl)-1,2,4-oxadiazole
73217-30-8

3-(chloromethyl)-5-(4-chlorophenyl)-1,2,4-oxadiazole

C25H33ClN4O5

C25H33ClN4O5

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 12h;79%
5-(3,4-Dimethoxyphenyl)-2-furaldehyde
62427-25-2

5-(3,4-Dimethoxyphenyl)-2-furaldehyde

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

ethyl (3R,4R,5S)-4-acetamido-5-(((5-(3,4-dimethoxyphenyl)furan-2-yl)methyl)amino)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

ethyl (3R,4R,5S)-4-acetamido-5-(((5-(3,4-dimethoxyphenyl)furan-2-yl)methyl)amino)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride In ethanol at 20℃;79%
benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

ethyl (3R,4R,5S)-4-acetamido-3-(pentan-3-yloxy)-5-(phenylsulfonamido)cyclohex-1-ene-1-carboxylate

ethyl (3R,4R,5S)-4-acetamido-3-(pentan-3-yloxy)-5-(phenylsulfonamido)cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 6h;79%
4-(Methylthio)benzaldehyde
3446-89-7

4-(Methylthio)benzaldehyde

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

ethyl (3R,4R,5S)-4-acetamido-3-(sec-butoxy)-5-((4(methylthio)benzyl)amino)cyclohex -1-ene-1-carboxylate

ethyl (3R,4R,5S)-4-acetamido-3-(sec-butoxy)-5-((4(methylthio)benzyl)amino)cyclohex -1-ene-1-carboxylate

Conditions
ConditionsYield
With sodium cyanoborohydride In ethanol at 20℃; for 6h;77.3%
3-thiophene carboxaldehyde
498-62-4

3-thiophene carboxaldehyde

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

ethyl (3R,4R,5S)-4-acetamido-3-(pentan-3-yloxy)-5-((thiophen-3-ylmethyl)amino)cyclohex-1-ene-1-carboxylate

ethyl (3R,4R,5S)-4-acetamido-3-(pentan-3-yloxy)-5-((thiophen-3-ylmethyl)amino)cyclohex-1-ene-1-carboxylate

Conditions
ConditionsYield
With sodium cyanoborohydride In methanol; ethanol at 20℃; for 6h;77%
With sodium cyanoborohydride In ethanol at 20℃; for 6h;
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

(3R,4R,5S)-4-acetamido-5-((4-nitrobenzyl)amino)-3-((pentan-3-yl)oxy)cyclohexene-1-ene-1-carboxylic acid ethyl ester

(3R,4R,5S)-4-acetamido-5-((4-nitrobenzyl)amino)-3-((pentan-3-yl)oxy)cyclohexene-1-ene-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
With sodium cyanoborohydride In methanol; ethanol at 20℃; for 6h;77%
With sodium cyanoborohydride In ethanol at 30℃; for 5h;76.3%
phenylacetic acid
103-82-2

phenylacetic acid

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

(3R,4R,5S)-ethyl 4-acetamido-5-(phenylacetamido)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

(3R,4R,5S)-ethyl 4-acetamido-5-(phenylacetamido)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;77%
(phenylthio)acetic acid chloride
7031-27-8

(phenylthio)acetic acid chloride

oseltamivir phosphate
204255-11-8

oseltamivir phosphate

C24H34N2O7S

C24H34N2O7S

Conditions
ConditionsYield
With dihydrogen peroxide In acetonitrile at 60℃; for 24h;77%

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