CAS No.196618-13-0,Oseltamivir Suppliers

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Basic Information

Molecular Structure:
CAS No.:	196618-13-0
Name:	Oseltamivir
Article Data:	66

Formula:	C₁₆H₂₈N₂O₄
Molecular Weight:	312.409
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;
EINECS:	1308068-626-2
Density:	1.08 g/cm³
Melting Point:	107-108 °C
Boiling Point:	473.3 °C at 760 mmHg
Flash Point:	240 °C
Solubility:	Soluble
PSA:	90.65000
LogP:	2.37660

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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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