184435-75-4

Basic information

• Product Name: (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one
• Synonyms: (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one
• CAS NO: 184435-75-4
• Molecular Weight: 208.281
• Mol File: 184435-75-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one(184435-75-4)
• EPA Substance Registry System: (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one(184435-75-4)

Safety Data

• Hazardous Substances Data: 184435-75-4(Hazardous Substances Data)

Upstream product

• 16088-62-3 (S)-Propylene oxide 
• 288585-37-5 (S)-4-Hydroxy-2-phenylsulfanyl-pentanoic acid 
• 103-04-8 (phenylthio)acetic acid 

Downstream Products

• 148123-43-7 (3R,5S)-5-Methyl-3-oct-7-ynyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 533924-09-3 (3RS,5S)-3-[(EZ,2R)-2-(tert-butyldimethylsilyloxy)-6-iodo-5-hexenyl]-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-2-one 
• 533923-95-4 (3RS,5S)-3-[(2R)-2-(tert-butyldimethylsilyloxy)-5-hexynyl]-5-methyl-3-(phenylsulfenyl)tetrahydrofuran-2-one 
• 912295-27-3 3-(3-chloro-2-hydroxy-propyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 1086570-03-7 (S)-3-((R)-2-(tert-butyldimethylsilyloxy)dodec-11-ynyl)-5-methyl-3-(phenylthio)dihydrofuran-2(3H)-one 
• 757971-87-2 3-(13-(tert-butyl-dimethylsilanyloxy)-13-{5-[1-(tert-butyl-dimethylsilanyloxy)tridecyl]-tetrahydrofuran-2-yl}tridecyl)-5-methyl-3-phenylsulfanyl-dihydrofuran-2-one 
• 862603-29-0 (S)-3-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-undec-10-enyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 862603-33-6 (5S)-3-[(R)-2-(tert-butyldimethylsilyloxy)non-8-enyl]-5-methyl-3-phenylthio-3H-dihydrofuran-2-one 
• 507480-44-6 3-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 184435-79-8 (S)-3-[7-((S)-2,2-Diethyl-[1,3]dioxolan-4-yl)-heptyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 
• 191993-41-6 (3RS,5S)-3-[3'-(tetrahydro-2-pyranyloxy)propyl]-5-methyl-3-(phenylsulfanyl)tetrahydrofuran-2-one 
• 288585-40-0 (E,Z,3RS,5S)-3-(9-iodonon-8-enyl)-5-methyl-3-(phenylsulfenyl)-tetrahydrofuran-2-one 

Relevant articles and documents

Absolute Configuration of (-)-Botryococcene

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Concise syntheses of the natural products (+)-sylvaticin and (+)-cis-sylvaticin

Two concise syntheses of the natural products cis-sylvaticin and sylvaticin are reported, using oxidative cyclization methodology as the key step. A sequential solvolysis/hydride shift/intramolecular reduction cascade was used to establish the trans stereochemistry of one of the THF rings of sylvaticin.

A modular synthesis of annonaceous acetogenins

A synthesis of four Annonaceous acetogenins, asiminocin, asimicin, asimin, and bullanin, by a modular approach from seven fundamental subunits, A-G, is described. The approach employs a central core aldehyde segment, C, to which are appended an aliphatic terminus, A or B, a spacer subunit, D or E, and a butenolide terminus, F or G. Coupling of the A, B, D, and E segments to the core aldehyde unit is effected by highly diastereoselective additions of enantiopure allylic indium or tin reagents. The butenolide termini are attached to the ACD, BCE, or BCD intermediates by means of a Sonogashira coupling. The design of the core, spacer, and termini subunits is such that any of the C30, C10, or C4 natural acetogenins or stereoisomers thereof could be prepared. IC50 values for the four aforementioned acetogenins against H-116 human colon cancer cells were found to be in the 10-3 to 10-4 μM range. The IC90 activities were ca. 10-3 μM for asimicin and asimin but only 0.1-1 μM for bullanin and asiminocin.