2',3'-dideoxy-5-fluoro-3'-thiacytidine hydrochloride
emtricitabine
Conditions | Yield |
---|---|
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 |
emtricitabine
Conditions | Yield |
---|---|
With triethylamine In ethanol at 50℃; for 1h; | 91.88% |
emtricitabine
Conditions | Yield |
---|---|
With Isopropyl acetate; triethylamine at 15 - 30℃; for 4h; Reagent/catalyst; | 90% |
In acetone for 2h; Reflux; | 87% |
emtricitabine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In methanol at 15 - 60℃; | 88.9% |
emtricitabine
Conditions | Yield |
---|---|
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% |
emtricitabine
Conditions | Yield |
---|---|
With methanol; potassium carbonate at 0 - 25℃; for 3h; | 87.34% |
emtricitabine
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 0 - 25℃; for 3h; | 86% |
With potassium carbonate In methanol at 0 - 25℃; for 3.5h; | 82% |
emtricitabine
Conditions | Yield |
---|---|
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% |
(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
emtricitabine
Conditions | Yield |
---|---|
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% |
emtricitabine
Conditions | Yield |
---|---|
With ammonia Ambient temperature; Yield given; |
(-)-(2R,5S)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N4-benzoylcytosine
emtricitabine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: tetra-n-butylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature 2: methanolic NH3 / Ambient temperature View Scheme |
4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-[1,3]-oxathiolan-5-yl]-(1H)-pyrimidin-2-one monosuccinate
emtricitabine
Conditions | Yield |
---|---|
With triethylamine In isopropyl alcohol at 20℃; for 5h; |
5-(4-acetylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester
emtricitabine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: methanesulfonic acid / methanol / 4 h 1.2: 0.17 h 2.1: sodium hydroxide; dipotassium hydrogenphosphate; sodium tetrahydroborate / water; industrially methylated spirit / 4 h / 18 - 22 °C 2.2: 22 - 42 °C 3.1: triethylamine / isopropyl alcohol; water / 6 h / 6 - 20 °C View Scheme |
4-amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolane-5-yl)-1H-pyrimidin-2-one 2-fluorobenzoic acid salt
emtricitabine
Conditions | Yield |
---|---|
With triethylamine In water; isopropyl alcohol at 6 - 20℃; for 6h; |
emtricitabine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: (S)-2-phenylglycine / methanol / Reflux 1.2: 8 h / 20 °C 2.1: 1,1'-bi-2-naphthol / methanol / Reflux 2.2: 0.5 h / pH 2 - 3 View Scheme |
N,N-dimethyl-formamide dimethyl acetal
emtricitabine
Conditions | Yield |
---|---|
In methanol at 20℃; for 21h; | 100% |
emtricitabine
Conditions | Yield |
---|---|
With hydrogenchloride In isopropyl alcohol at 10 - 20℃; for 2h; Solvent; Temperature; | 93.6% |
tert-butyldimethylsilyl chloride
emtricitabine
4-amino-1-((2R,5S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoropyrimidin-2(1H)-one
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 18h; | 90% |
With 1H-imidazole In tetrahydrofuran at 20℃; for 2h; Concentration; Inert atmosphere; Cooling; |
emtricitabine
isobutyl chloroformate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere; | 83% |
emtricitabine
methyl chloroformate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; | 68% |
dodecyl 1H-imidazole-1-carboxylate
emtricitabine
Conditions | Yield |
---|---|
With pyridine; potassium hydroxide In dichloromethane at 20℃; for 18h; Inert atmosphere; | 67% |
emtricitabine
carbonochloridic acid, butyl ester
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere; | 60% |
emtricitabine
Conditions | Yield |
---|---|
Stage #1: emtricitabine With tert-butylmagnesium chloride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: C17H21F5NO8P In tetrahydrofuran at 0 - 20℃; for 20h; | 53% |
tetra(n-butyl)ammonium hydroxide
emtricitabine
Conditions | Yield |
---|---|
Stage #1: emtricitabine With trichlorophosphate at 0℃; for 1h; Inert atmosphere; Stage #2: With water for 1h; Cooling with ice; Stage #3: tetra(n-butyl)ammonium hydroxide In water pH=7.0; | 36% |
Conditions | Yield |
---|---|
With copper(l) iodide; 9-azabicyclo<3.3.1>nonane-N-oxyl; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In N,N-dimethyl-formamide at 20℃; under 760.051 Torr; for 4h; Sealed tube; | 35% |
emtricitabine
Allyl chloroformate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 15h; Inert atmosphere; | 23% |
emtricitabine
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride In water for 24h; pH=6.0; | 16% |
emtricitabine
salicylic acid
Conditions | Yield |
---|---|
In water at 80℃; | 13% |
emtricitabine
(-)-5'-O-(t-butyldimethylsilyl)-N4-(4,4'-dimethoxytrityl)-5-fluoro-2',3'-dideoxy-3'-thiacytidine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C 2: pyridine / 0 - 20 °C View Scheme |
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
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 (CAS NO.143491-57-0) is used as an anti-AIDS drug. It is also used as an antiviral drug.
Hazardous Substances Data Emtricitabine (CAS NO.143491-57-0): 143491-57-0(Hazardous Substances Data)
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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