75636-74-7

Basic information

• Product Name: (5E)-5-phenethylsulfinyl-PGI₂ methyl ester
• CAS NO: 75636-74-7
• Molecular Weight: 490.661
• Mol File: 75636-74-7.mol

Chemical Properties

• CAS DataBase Reference: (5E)-5-phenethylsulfinyl-PGI₂ methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (5E)-5-phenethylsulfinyl-PGI₂ methyl ester(75636-74-7)
• EPA Substance Registry System: (5E)-5-phenethylsulfinyl-PGI₂ methyl ester(75636-74-7)

Safety Data

• Hazardous Substances Data: 75636-74-7(Hazardous Substances Data)

Upstream product

• 931-59-9 benzenesulfenyl chloride 
• 61799-74-4 PGI₂ methyl ester 
• 75636-73-6 (5E)-5-phenylthio-PGI₂ methyl ester 
• 61799-74-4 5-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-(2Z)-ylidene]-pentanoic acid methyl ester 
• 75636-73-6 5-[(3aR,5R,6aS)-5-Hydroxy-4-((E)-(S)-3-hydroxy-oct-1-enyl)-hexahydro-cyclopenta[b]furan-(2E)-ylidene]-5-phenylsulfanyl-pentanoic acid methyl ester 
• 78824-82-5 11,15-O-bis(tert-butyldimethylsilyl)PGI₂ methyl ester 
• 78824-84-7 (5E)-5-phenylthio-PGI₂ 11,15-O-bis(t-butyldimethylsilyl) methyl ester 

Relevant articles and documents

SYNTHESIS OF CHEMICALLY STABLE PROSTACYCLIN ANALOGS

Syntheses of several stable PGI2 analogs substituted by an electron-withdrawing substituent at C-5 or C-7 are described.Reaction of PGI2 methyl ester (1) with benzenesulfenyl chloride gave (5E)-5-phenylthio-PGI2 (2) or (5R)-5-phenylthio-Δ6-PGI1 (5) according to the reaction condition employed.Allyl sulfide 5 was transformed into (7S)-7-hydroxy-PGI2 (11) and (7S)-7-acetoxy PGI2 (12) via stereocontrolled sulfoxide-sulfenate rearrangement, and alcohol 11 was further transformed into (7S)-7-fluoro-PGI2 (14).These PGI2 analogs were found much more stable than PGI2.

Reaction of prostacyclin methyl ester with benzenesulfenyl chloride preparation of stable prostacyclin analogs

Several phenyl sulfides including stable 5- and 7-phenylthioprostacyclins were obtained by the reaction of the vinyl ether (1) and prostacyclin methyl ester (5) with PhSCl.