189954-93-6

Basic information

• Product Name: 2(5H)-Furanone, 5-ethyl-5-methyl-3-(1-methylethoxy)-4-[4-(methylsulfonyl)phenyl]-, (5S)-
• CAS NO: 189954-93-6
• Molecular Formula: C17H22O5S
• Molecular Weight: 338.425
• Mol File: 189954-93-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2(5H)-Furanone, 5-ethyl-5-methyl-3-(1-methylethoxy)-4-[4-(methylsulfonyl)phenyl]-, (5S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(5H)-Furanone, 5-ethyl-5-methyl-3-(1-methylethoxy)-4-[4-(methylsulfonyl)phenyl]-, (5S)-(189954-93-6)
• EPA Substance Registry System: 2(5H)-Furanone, 5-ethyl-5-methyl-3-(1-methylethoxy)-4-[4-(methylsulfonyl)phenyl]-, (5S)-(189954-93-6)

Safety Data

• Hazardous Substances Data: 189954-93-6(Hazardous Substances Data)

Upstream product

• 1025800-69-4 Trifluoro-methanesulfonic acid (S)-2-ethyl-4-isopropoxy-2-methyl-5-oxo-2,5-dihydro-furan-3-yl ester 
• 455878-43-0 (S)-1-ethyl-1-methyl-2-[(4-methylthio)phenyl]-2-oxoethyl 2-(1-methylethoxy)acetate 
• 455878-42-9 (S)-2-hydroxy-2-methyl-1-[4-(methylthio)phenyl]butan-1-one 
• 499140-46-4 (S)-methyl 2-methyl-2-[2-(1-methylethoxy)acetyloxy]butanoate 
• 455878-41-8 (S)-2-hydroxy-2-methyl-1-(pyrrolidin-1-yl)butan-1-one 
• 499140-47-5 (S)-5-ethyl-4-hydroxy-5-methyl-3-(1-methylethoxy)-3-oxolen-2-one 
• 208117-20-8 methyl (2S)-2-hydroxy-2-methylbutanoate 
• 37505-07-0 (S)-2-hydroxy-2-methylbutyric acid 
• 189956-08-9 (S)-2-Methyl-1-(4-methylsulfonylphenyl)-prop-2-en-1-ol 
• 189955-79-1 2-bromo-2-methyl-1-[4-(methylsulfonyl)phenyl]propan-1-one 
• 516453-68-2 2-methyl-1-[4-(methylsulfonyl)phenyl]prop-2-en-1-one 
• 33445-07-7 2-isopropoxyacetic acid 
• 455878-44-1 (S)-1-ethyl-1-methyl-2-[(4-methylsulfonyl)phenyl]-2-oxoethyl 2-(1-methylethoxy)acetate 
• 499140-48-6 (S)-5-ethyl-5-methyl-3-(1-methylethoxy)-4-(4-(methylthio)phenyl)-3-oxolen-2-one 

Downstream Products

• 853658-46-5 (5S)-5-ethyl-3-isopropoxy-5-methyl-4-[4-(methylsulfonyl)phenyl]furan-2(5H)-thione 
• 853658-51-2 {(7S)-7-ethyl-9-isopropoxy-7-methyl-8-[4-(methylsulfonyl)phenyl]-1,4,6-trioxaspiro[4.4]non-8-en-2-yl}methanol 
• 906538-77-0 N-[(5S)-5-ethyl-3-isopropoxy-5-methyl-4-[4-(methylsulfonyl)phenyl]furan-2(5H)-ylidene]-L-serine methyl ester 

Relevant articles and documents

An approach for the enantioselective synthesis of biologically active furanones from a Morita-Baylis-Hillman adduct

Herein, we disclose an approach for the asymmetric synthesis of both enantiomers of an anti-inflammatory furanone. The approach is based on the utilization of a Morita-Baylis-Hillman adduct as starting material and has as key step a selective epoxide-opening/benzylic oxidation mediated by Palladium (II). This sequence afforded an advanced intermediate, which was used to accomplish the total synthesis. Experimental evidences allowed us to suggest a mechanistic proposal for the oxidation Palladium(II)-mediated.

Discovery of a potent and selective COX-2 inhibitor in the alkoxy lactone series with optimized metabolic profile.

The COX-2 inhibitor DFP [5,5-dimethyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone] was found to have a long half-life in humans. Analogues have been characterized in order to optimize pharmacokinetics. This has lead to the discovery of 5(S)-(5-ethyl-5-methyl-3-(2-propoxy)-4-methanesulfonylphenyl)-2(5H)-furanone analogue 11 a potent and selective COX-2 inhibitor which is metabolized to a greater extent than DFP upon incubation with rat and human hepatocytes, suggesting a shorter half-life in humans.