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Oseltamivir

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Name

Oseltamivir

EINECS 1308068-626-2
CAS No. 196618-13-0 Density 1.08 g/cm3
PSA 90.65000 LogP 2.37660
Solubility Soluble Melting Point 107-108 °C
Formula C16H28N2O4 Boiling Point 473.3 °C at 760 mmHg
Molecular Weight 312.409 Flash Point 240 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 196618-13-0 (Oseltamivir) Hazard Symbols N/A
Synonyms

1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, [3R-(3a,4b,5a)]-;GOP-A-Flu;GS 4104;Tamiflu-Free;Tamvir;

Article Data 66

Oseltamivir Synthetic route

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

196618-13-0

oseltamivir

Conditions
ConditionsYield
With 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 50℃; for 2.21667h;88.7%
Stage #1: ethyl (3R,4R,5S)-4-N-acetylamino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate With 1,3-dimethylbarbituric acid; palladium diacetate; triphenylphosphine In ethanol at 35℃; for 2h; Inert atmosphere;
Stage #2: With phosphoric acid In acetone for 2h;
83.69%
With tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid
367252-68-4

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

196618-13-0

oseltamivir

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 4h; Inert atmosphere;92%
Stage #1: (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate With hydrogenchloride; water In ethanol at 50℃; for 1h;
Stage #2: With sodium hydrogencarbonate In water
90%
With hydrogenchloride In tetrahydrofuran; ethyl acetate for 0.05h;13.8 mg
312904-18-0

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

196618-13-0

oseltamivir

Conditions
ConditionsYield
With ethanolamine; palladium 10% on activated carbon In ethanol at 20℃; for 3h; Heating / reflux;70%
With palladium on activated charcoal; ethanolamine In ethanol for 3h; Heating;
With ethanolamine; palladium on activated charcoal In ethanol for 3h; Heating;

(1S,2R,3S,4R,5S)-4-acetylamino-3-(1-ethylpropoxy)-5-nitro-2-p-tolylsulfanylcyclohexanecarboxylic acid ethyl ester

196618-13-0

oseltamivir

Conditions
ConditionsYield
Stage #1: (1S,2R,3S,4R,5S)-4-acetylamino-3-(1-ethylpropoxy)-5-nitro-2-p-tolylsulfanylcyclohexanecarboxylic acid ethyl ester With chloro-trimethyl-silane; zinc In ethanol at 23 - 70℃; for 2h; Inert atmosphere;
Stage #2: With ammonia In ethanol at 0℃; for 0.166667h;
Stage #3: With potassium carbonate In ethanol at 23℃; for 6h;
85%
Stage #1: (1S,2R,3S,4R,5S)-4-acetylamino-3-(1-ethylpropoxy)-5-nitro-2-p-tolylsulfanylcyclohexanecarboxylic acid ethyl ester With chloro-trimethyl-silane; zinc In ethanol at 70℃; for 2h; Inert atmosphere;
Stage #2: With ammonia In ethanol at 0℃; for 0.166667h; Inert atmosphere;
Stage #3: With potassium carbonate In ethanol at 23℃; for 9h; Inert atmosphere;
81%
Stage #1: (1S,2R,3S,4R,5S)-4-acetylamino-3-(1-ethylpropoxy)-5-nitro-2-p-tolylsulfanylcyclohexanecarboxylic acid ethyl ester With chloro-trimethyl-silane; zinc In ethanol at 70℃; for 2h;
Stage #2: With ammonia; potassium carbonate In ethanol at 20℃; for 6h;
80%
1041262-68-3

(3R,4R,5S)-4-acetamido-5-(1,3-dioxoisoindol-2-yl)-3-(pentyl-3-yloxy)cyclohexyl-ethyl-1-ene-1-carboxylate

196618-13-0

oseltamivir

Conditions
ConditionsYield
With hydrazine In ethanol at 68℃; for 10h;100%
With hydrazine In ethanol at 68℃; for 10h; Inert atmosphere;100%
With hydrazine In ethanol at 68℃; for 11h; Schlenk technique; Inert atmosphere;86%

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

196618-13-0

oseltamivir

Conditions
ConditionsYield
With pyrrolidine; tetrakis(triphenylphosphine) palladium(0) In ethanol for 0.5h;95.1%
With 1,3-dimethylbarbituric acid; triphenylphosphine; palladium on activated charcoal In ethanol; water at 80℃; for 1h;
1197396-47-6

(3R,4R,5S)-ethyl-4-(N-acetylacetamide)-5-(1,3-dioxoisoindolin-2-yl)-3-(3-pentyloxy)cyclohex-1-ene carboxylate

196618-13-0

oseltamivir

Conditions
ConditionsYield
Stage #1: (3R,4R,5S)-ethyl-4-(N-acetylacetamide)-5-(1,3-dioxoisoindolin-2-yl)-3-(3-pentyloxy)cyclohex-1-ene carboxylate With hydrazine hydrate In ethanol at 50℃; for 14h; Inert atmosphere;
Stage #2: With hydrogenchloride; water In ethanol
Stage #3: With ammonium hydroxide In water pH=11;
96%

C21H36N2O6

196618-13-0

oseltamivir

Conditions
ConditionsYield
With trifluoroacetic acid In isopropyl alcohol at 0 - 30℃; for 7h; Solvent; Reagent/catalyst; Temperature;96%
204255-06-1

oseltamivir

196618-13-0

oseltamivir

Conditions
ConditionsYield
With hydrogen at 20℃; under 380.026 Torr; for 3h;98.5%
With tributylphosphine; acetic acid In ethanol; water at 5 - 25℃; for 5.5 - 9h;97%
With triphenylphosphine In tetrahydrofuran; water at 50℃; for 10h;96%

(1S,2R,3S,4R,5S)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)-2-(p-tolylthio)cyclohexanecarboxylate

196618-13-0

oseltamivir

Conditions
ConditionsYield
With potassium carbonate In ethanol at 23℃; for 4h; retro Michael reaction;91%
With potassium carbonate In ethanol at 23℃; for 4h; Product distribution / selectivity;91%
Stage #1: (1S,2R,3S,4R,5S)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)-2-(p-tolylthio)cyclohexanecarboxylate With ammonia In ethanol at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: With potassium carbonate In ethanol at 23℃; for 6h; Inert atmosphere;
45.2 mg

Oseltamivir Specification

The 1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)- , with cas register number of 196618-13-0, belongs to the classification codes of (1)anti-infective agents ; (2)antiviral agents ; (3)enzyme inhibitors ; (4)influenza treatment. It also has other names such as Oseltamivir ; Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate . Its IUPAC name is ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate . And its systematic name is also called ethyl (3R,4R,5S)-4-(acetylamino)-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate .

Physical properties of 1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)- are: (1) ACD/LogP: 1.50 ; (2)# of Rule of 5 Violations: 0 ; (3)ACD/LogD (pH 5.5): -1.02 ; (4) ACD/LogD (pH 7.4): 0.69 ; (5) ACD/BCF (pH 5.5): 1 ; (6) ACD/BCF (pH 7.4): 1.25 ; (7) ACD/KOC (pH 5.5): 1 ; (8) ACD/KOC (pH 7.4): 24.06 ; (9) #H bond acceptors: 6 ; (10) #H bond donors: 3 ; (11) #Freely Rotating Bonds: 9 ; (12) Index of Refraction: 1.502 ; (13) Molar Refractivity: 84.66 cm3 ; (14) Molar Volume: 286.7 cm3 ; (15) Surface Tension: 41.1 dyne/cm ; (16) Density: 1.08 g/cm3 ; (17) Flash Point: 240 °C ; (18) Enthalpy of Vaporization: 73.64 kJ/mol ; (19) Boiling Point: 473.3 °C at 760 mmHg ; (20) Vapour Pressure: 3.98E-09 mmHg at 25°C.

Uses of 1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)- : This compound is an acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits neuraminidase. It has been used as a drug for treatment of influenza.

You can still convert the following datas into molecular structure:
(1) SMILES:O=C(OCC)/C1=C/[C@@H](OC(CC)CC)[C@H](NC(=O)C)[C@@H](N)C1;
(2) InChI:InChI=1/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1;
(3) InChIKey:VSZGPKBBMSAYNT-RRFJBIMHBB

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