138098-75-6

Basic information

• Product Name: (R)-(+)-ethyl-3-phenylsulfanyl-3-phenylpropionate
• Synonyms: (R)-(+)-ethyl-3-phenylsulfanyl-3-phenylpropionate
• CAS NO: 138098-75-6
• Molecular Weight: 286.395
• Mol File: 138098-75-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-(+)-ethyl-3-phenylsulfanyl-3-phenylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-ethyl-3-phenylsulfanyl-3-phenylpropionate(138098-75-6)
• EPA Substance Registry System: (R)-(+)-ethyl-3-phenylsulfanyl-3-phenylpropionate(138098-75-6)

Safety Data

• Hazardous Substances Data: 138098-75-6(Hazardous Substances Data)

Upstream product

• 2216-94-6 phenylpropynoic acid ethyl ester 
• 536-74-3 phenylacetylene 
• 34875-02-0 ethyl (Z)-3-phenyl-3-(phenylthio)acrylate 
• 34875-12-2 ethyl (E)-3-phenyl-3-(phenylthio)acrylate 
• 199847-19-3 (R)-3-Phenyl-3-(2-trimethylsilanyl-phenylsulfanyl)-propionic acid methyl ester 
• 103-26-4 methyl cinnamate 
• 33356-45-5 2-(Trimethylsilyl)benzenethiol 
• 64-17-5 ethanol 
• 392668-05-2 (+)-(R)-methyl 3-phenyl-3-phenylsulfanylpropanoate 
• 33401-74-0 ethyl (3R)-3-hydroxy-3-phenylpropionate 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 138098-76-7 (-)-3-(phenylthio)-3-phenylpropionic acid 

Relevant articles and documents

Simple preparation of enantiomeric Michael adducts of thiophenol to chalcones: Easily available new chiral building blocks

A facile and enantioselective method for the multigram preparation of the title compounds is described. The Michael addition of thiophenols to chalcones catalyzed by (+)-cinchonine, followed by crystallization, led to the corresponding adducts 2 in up to >95% e.e. The stereoselective Beckmann rearrangement of the oxime of (+)-1,3-diphenyl-3-phenylsulfanylpropan-1-one 2a gives the anilide of (R)-(+)-3-phenyl-3-phenylsulfanylpropanoic acid (as determined by X-ray analysis) and alcoholysis leads to the corresponding enantiomerically pure ethyl ester.

Chiral amino ether-controlled catalytic enantioselective arylthiol conjugate additions to α,β-unsaturated esters and ketones: Scope, structural requirements, and mechanistic implications

Asymmetric conjugate addition reaction of 2-trimethylsilylbenzenethiol with enoates and enones is catalyzed by a chiral amino ether-lithium thiolate complex and affords adducts with high enantioselectivity. Both the s-cis conformation and a steric wall at one side of the carbonyl group are structural requirements in substrates yielding adducts with high enantioselectivity. Reactions with tert-butyl enones gave addition products with high enantioselectivity. Construction of two contiguous chiral centers was possible by this addition-protonation sequence. Methyl tiglate was stereoselectively converted to a single syn-adduct of 95% enantiomeric excess (ee) bearing two contiguous chiral centers. Methyl 2-phenyl-2-butenoate was converted to a single syn-adduct of 95% ee, which was desulfurized to methyl 2-phenylbutanoate of 95% ee. These additions generate a transient lithium enolate that is protonated by a thiol anti to the C-S bond, giving the corresponding product having two adjacent stereocenters.

A novel chemoenzymatic enantioselective synthesis of some clinically effective CNS drugs and related compounds

We have demonstrated in this study a novel route for the synthesis of benzothiopyran and benzothiazepin ring systems along with the synthesis of optically pure, clinically effective drugs tomoxetine, fluoxetine and thiazesim.