144371-00-6

Basic information

• Product Name: EMTRICITABINE
• Synonyms: (-)-B-2',3'-DIDEOXY-5-FLUORO-3'-THIACYTIDINE;4-AMINO-5-FLUORO-1-[(2R,5S)-2-HYDROXYMETHYL)-1,3-OXATHIOLAN-5-YL]-2-(1H-PYRIMIDINONE;524W91;BW-52491;COVIRACIL
• CAS NO: 144371-00-6
• Molecular Formula: C8H10FN3O3S
• Molecular Weight: 247.2467032
• Mol File: 144371-00-6.mol
• Article Data: 35

Chemical Properties

• Boiling Point: 443.3±55.0 °C(Predicted)
• Appearance: /
• Density: 1.82±0.1 g/cm3(Predicted)
• PKA: 13.83±0.10(Predicted)
• CAS DataBase Reference: EMTRICITABINE(CAS DataBase Reference)
• NIST Chemistry Reference: EMTRICITABINE(144371-00-6)
• EPA Substance Registry System: EMTRICITABINE(144371-00-6)

Safety Data

• Hazardous Substances Data: 144371-00-6(Hazardous Substances Data)

Upstream product

• 144371-00-6 Emtricitrabine 
• 143446-69-9 cis-{5-(4-amino-5-fluoro-2-oxo-1(2H)-pyrimidinyl)-1,3-oxathiolan-2-yl}methyl butanoate 
• 149819-36-3 (+)-(2S,5R)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-benzoylcytosine 
• 149819-37-4 (-)-(2S,5S)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N₄-benzoylcytosine 
• 145986-20-5 (+)-(2R,5R)-5-fluoro-1-<2-<<(tert-butyldiphenylsilyl)oxy>methyl>-1,3-oxathiolan-5-yl>-N⁴-benzoylcytosine 
• 1321928-76-0 4-amino-5-fluoro-1-((2R,5S)-2-hydroxymethyl-[1,3]oxathiolane-5-yl)-1H-pyrimidin-2-one 2-fluorobenzoic acid salt 
• 1321928-75-9 5-(4-acetylamino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-[1,3]oxathiolane-2-carboxylic acid 2-isopropyl-5-methyl-cyclohexyl ester 
• 1313482-37-9 4-amino-5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-[1,3]-oxathiolan-5-yl]-(1H)-pyrimidin-2-one monosuccinate 
• 258832-61-0 2',3'-dideoxy-5-fluoro-3'-thiacytidine hydrochloride 
• 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-oxathiolane-2-carboxylate 

Downstream Products

• 144371-00-6 (+)-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane 
• 144371-00-6 (-)-2-hydroxymethyl-5-(5-fluorocytosin-1-yl)-1,3-oxathiolane 
• 137530-41-7 racivir 
• 144371-00-6 (-)-(2S,5S)-5-fluoro-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine 
• 144371-00-6 (+)-(2R,5R)-5-fluoro-1-<2-(hydroxymethyl)-1,3-oxathiolan-5-yl>cytosine 
• 1365246-91-8 C₅₈H₇₂F₂N₆O₁₂S 
• 1365246-86-1 (-)-N₄-(4,4'-dimethoxytrityl)-5-fluoro-2',3'-dideoxy-3'-thiacytidine 
• 1365246-85-0 (-)-5'-O-(t-butyldimethylsilyl)-N₄-(4,4'-dimethoxytrityl)-5-fluoro-2',3'-dideoxy-3'-thiacytidine 
• 1365246-84-9 4-amino-1-((2R,5S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-1,3-oxathiolan-5-yl)-5-fluoropyrimidin-2(1H)-one 

Relevant articles and documents

Synthesis of (±)-Emtricitabine and (±)-Lamivudine by Chlorotrimethylsilane-Sodium Iodide-Promoted Vorbrüggen Glycosylation

By simple combination of water and sodium iodide (NaI) with chlorotrimethylsilane (TMSCl), promotion of a Vorbrüggen glycosylation en route to essential HIV drugs emtricitabine (FTC) and lamivudine (3TC) is achieved. TMSCl-NaI in wet solvent (0.1 M water)

Asymmetric synthesis method of emtricitabine

The present invention provides an asymmetric synthesis method of emtricitabine. L-menthyl chloroformate is used as raw material to condense with 2-chloro-1-ethanol, then hydrolyze under the conditionof catalyst to obtain acetaldehyde alcohol optically active ester which is then induced by chiral promoter to condense with 2, 5-dihydroxyl-1,4-dithiane to give trans 5-hydroxyl-1,3-oxythiacyclopentane-2-methyl-L-menthol carbonate, the trans 5-hydroxyl-1,3-oxythiacyclopentane-2-methyl-L-menthol carbonate is halogenated and coupled with silanized 5-fluorocytosine, emtricitabine is obtained by removing the chiral auxiliary agent under the condition of weak alkalinity. As that raw materials used in the whole synthesis process are cheap and easy to obtain, the raw material utilization ratio is high, so that the synthesis cost of the emtricitabine is greatly reduced, and the synthesis process is simple, the synthesis condition is mild, the yield of the obtained emtricitabine is high, meanwhile,the chiral assistant is easy to remove in the synthesis process, the three waste pollutants generated are less, and the preparation method is suitable for the large-scale industrial production of theemtricitabine.

Emtricitabine synthesis method

The invention provides an emtricitabine synthesis method, which comprises: carrying out condensation on cheap and easily available dihaloacetic acid as a raw material and L-menthol, hydrolyzing to obtain menthyl glyoxylate hydrate, condensing with 2,5-dihydroxy-1,4-dithiane, carrying out halogenation, coupling with silylated 5-flucytosine, reducing, carrying out salt forming with salicylic acid toobtain emtricitabine salicylate, and finally re-crystallizing to obtain optically pure emtricitabine. According to the present invention, the whole synthesis process has characteristics of inexpensive and easily available raw materials, simple synthesis process and mild synthesis conditions, such that the synthesis cost of emtricitabine is substantially reduced; various raw materials have characteristics of good reaction selectivity and high utilization rate, such that the yield of the obtained emtricitabine is high; and the chiral substrate is easily removed during the synthesis, and the generated three-waste pollutants are less, such that the method is suitable for industrial large-scale production of emtricitabine.