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Emtricitabine

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Name

Emtricitabine

EINECS 604-363-1
CAS No. 143491-57-0 Density 1.82 g/cm3
PSA 115.67000 LogP 0.12620
Solubility N/A Melting Point 136-140 °C
Formula C8H10FN3O3S Boiling Point 443.3 °C at 760 mmHg
Molecular Weight 247.25 Flash Point 221.9 °C
Transport Information N/A Appearance white to off-white crystalline solid
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 143491-57-0 (Emtricitabine) Hazard Symbols N/A
Synonyms

2(1H)-Pyrimidinone,4-amino-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, (2R-cis)-;(-)-2',3'-Dideoxy-5-fluoro-3'-thiacytidine;(-)-2'-Deoxy-5-fluoro-3'-thiacytidine;(-)-FTC;524W91;BW 1592;BW 524W91;Coviracil;Emtriva;FTC, (-)-;

Article Data 28

Emtricitabine Synthetic route

258832-61-0

2',3'-dideoxy-5-fluoro-3'-thiacytidine hydrochloride

143491-57-0

emtricitabine

Conditions
ConditionsYield
With triethylamine In methanol at 15 - 60℃;93.2%
With triethylamine In methanol at 25 - 65℃; for 0.25h; Heating / reflux;82%
With tributyl-amine In dichloromethane at 25 - 35℃; for 5.5h;
Amberlite LA2 liquid ion-exchange resin;25 g

(2R,5S)-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]cytosine salicylate

143491-57-0

emtricitabine

Conditions
ConditionsYield
With triethylamine In ethanol at 50℃; for 1h;91.88%

4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-1,2-dihydropyrimidin-2-one; benzoic acid

143491-57-0

emtricitabine

Conditions
ConditionsYield
With Isopropyl acetate; triethylamine at 15 - 30℃; for 4h; Reagent/catalyst;90%
In acetone for 2h; Reflux;87%

C8H10FN3O3S*BrH

143491-57-0

emtricitabine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In methanol at 15 - 60℃;88.9%

(+/-)-cis-2',3'-dideoxy-5-fluoro-3'-thiacytidine

143491-57-0

emtricitabine

Conditions
ConditionsYield
Stage #1: (+/-)-cis-2',3'-dideoxy-5-fluoro-3'-thiacytidine With 1,1'-bi-2-naphthol In methanol Reflux;
Stage #2: With hydrogenchloride In water; ethyl acetate for 0.5h; pH=2 - 3;
88.9%

C23H20FN3O6S

143491-57-0

emtricitabine

Conditions
ConditionsYield
With methanol; potassium carbonate at 0 - 25℃; for 3h;87.34%

5S-(5'-fluorocytosinyl)-1,3-oxathiolane-2R-methyl-L-menthol carbonate

143491-57-0

emtricitabine

Conditions
ConditionsYield
With potassium carbonate In methanol at 0 - 25℃; for 3h;86%
With potassium carbonate In methanol at 0 - 25℃; for 3.5h;82%

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[5-fluoro-2-oxo-4-(phenylcarboxamido)-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate

143491-57-0

emtricitabine

Conditions
ConditionsYield
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[5-fluoro-2-oxo-4-(phenylcarboxamido)-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate With methanol at 40℃; Inert atmosphere;
Stage #2: With sodium tetrahydroborate; dipotassium hydrogenphosphate; water; sodium hydroxide In methanol at 20℃; for 1h; diastereoselective reaction;
75%
764659-72-5

(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathialane-2-carboxylate

143491-57-0

emtricitabine

Conditions
ConditionsYield
With sodium tetrahydroborate; dipotassium hydrogenphosphate; water; sodium hydroxide In ethanol at 20℃; Temperature;70%
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-(4-amino-5-fluoro-2-oxo-1,2-dihydro-1-pyrimidinyl)-1,3-oxathiolane-2-carboxylate With sodium tetrahydroborate In methanol at -5℃; for 5h; Inert atmosphere;
Stage #2: With isopropyl alcohol In water at 60℃; for 1h;
Stage #3: With methanol In water Product distribution / selectivity;
65%
With methanol; sodium tetrahydroborate at -7 - -5℃; for 6h; Product distribution / selectivity; Inert atmosphere;65%

N-[5-Fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide

143491-57-0

emtricitabine

Conditions
ConditionsYield
With ammonia Ambient temperature; Yield given;

Emtricitabine Chemical Properties

Molecular Structure:
Molecular Formula: C8H10FN3O3S
Molecular Weight: 247.2467
IUPAC Name: 4-Amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one
Synonyms of Emtricitabine (CAS NO.143491-57-0): Truvada ; (-)-2'-Deoxy-5-fluoro-3'-thiacytidine ; (-)-FTC ; (2R-cis)-4-Amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-2(1H)-pyrimidinone ; 2'-Deoxy-5-fluoro-3'-oxa-4'-thiocytidine ; 2'-Deoxy-5-fluoro-3'-thiacytidine ; 2-FTC ; 5-Fluoro-1-((2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine ; 524W91 ; BW 1592 ; BW 524W91 ; BW524W91 ; Coviracil ; DRG-0208 ; Emtriva ; FTC ; FTC, (-)- ; HSDB 7337 ; UNII-G70B4ETF4S ; dOTFC ; 2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-(2-(hydroxymethyl)-1,3-oxathiolan-5-yl)-, (2R-cis)-
CAS NO: 143491-57-0
Classification Code: Anti-Infective Agents ; Antiretroviral ; Antiviral Agents ; Antiviral [treatment of HIV-1 and hepatitis B infections]
Melting point: 136-140°C 
Polar Surface Area: 79.67 Å2
Index of Refraction: 1.731
Molar Refractivity: 54.01 cm3
Molar Volume: 135.1 cm3
Surface Tension: 72.8 dyne/cm
Density: 1.82 g/cm3
Flash Point: 221.9 °C
Enthalpy of Vaporization: 80.89 kJ/mol
Boiling Point: 443.3 °C at 760 mmHg
Vapour Pressure: 1.01E-09 mmHg at 25°C

Emtricitabine History

Dr. Dennis C. Liotta, Dr. Raymond Schinazi and Dr. Woo-Baeg Choi of Emory University and licensed to Triangle Pharmaceuticals discovered Emtricitabine (CAS NO.143491-57-0) by Emory in 1996. Triangle Pharmaceuticals was acquired in 2003 by Gilead Sciences, who completed development and now market the product with the brand name Emtriva.

Emtricitabine Uses

 Emtricitabine (CAS NO.143491-57-0) is used as an anti-AIDS drug. It is also used as an antiviral drug.

Emtricitabine Safety Profile

Hazardous Substances Data Emtricitabine (CAS NO.143491-57-0): 143491-57-0(Hazardous Substances Data)

Emtricitabine Specification

 Emtricitabine (CAS NO.143491-57-0) works by inhibiting reverse transcriptase which can help to lower the amount of HIV and increase the number of immune system cells.

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