133760-93-7

Basic information

• Product Name: (E)-(S)_s-3-t-butoxycarbonyl-3-p-tolylsulfinylpropenoic acid
• Synonyms: (E)-(S)_s-3-t-butoxycarbonyl-3-p-tolylsulfinylpropenoic acid
• CAS NO: 133760-93-7
• Molecular Weight: 310.371
• Mol File: 133760-93-7.mol

Chemical Properties

• CAS DataBase Reference: (E)-(S)_s-3-t-butoxycarbonyl-3-p-tolylsulfinylpropenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(S)_s-3-t-butoxycarbonyl-3-p-tolylsulfinylpropenoic acid(133760-93-7)
• EPA Substance Registry System: (E)-(S)_s-3-t-butoxycarbonyl-3-p-tolylsulfinylpropenoic acid(133760-93-7)

Safety Data

• Hazardous Substances Data: 133760-93-7(Hazardous Substances Data)

Upstream product

• 58059-08-8 tert-butyl (R)-p-toluenesulfinylacetate 
• 298-12-4 Glyoxilic acid 

Downstream Products

• 139118-95-9 methyl (S₂,S₃,S₆,S₇,S_S)-2-bromo-4-oxa-5-oxo-9-p-tolylsulfinyltricycle<4.3.0.0^3,7>nonane-7-carboxylate 
• 133761-01-0 t-butyl (S₂,S₃,S₆,S₉,S_S)-2-bromo-4-oxa-5-oxo-9-p-tolylsulfinyltricycle<4.2.1.0^3,7>nonane-9-carboxylate 
• 139237-41-5 (S₁,R₂,S₃,R₄,S_S)-2-t-butoxycarbonyl-3-methoxycarbonyl-2-p-tolylsulfinylbicycle<2.2.1>hept-5-ene 
• 133760-96-0 (R₁,R₂,S₃,S₄,S_S)-2-t-butoxycarbonyl-3-methoxycarbonyl-2-p-tolylsulfinylbicycle<2.2.1>hept-5-ene 
• 133814-09-2 (S₁,S₂,R₃,R₄,S_S)-2-t-butoxycarbonyl-3-methoxycarbonyl-2-p-tolylsulfinylbicycle<2.2.1>hept-5-ene 
• 133760-96-0 (1R,2S,3R,4S)-2-(Toluene-4-sulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester 
• 133760-96-0 (1S,2S,3R,4R)-2-(Toluene-4-sulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester 
• 133760-96-0 (1R,2R,3S,4S)-2-(Toluene-4-sulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester 
• 133760-96-0 (1S,2R,3S,4R)-2-(Toluene-4-sulfinyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid 2-tert-butyl ester 3-methyl ester 
• 133761-01-0 (1S,2S,3S,6S,7R,9S)-2-Bromo-5-oxo-9-(toluene-4-sulfinyl)-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid tert-butyl ester 
• 133760-99-3 (1S,2S,3S,6S,7S,9R)-2-Iodo-5-oxo-6-(toluene-4-sulfinyl)-4-oxa-tricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid methyl ester 
• 133761-00-9 methyl (S₂,S₃,S₆,R₉,S_S)-2-bromo-4-oxa-5-oxo-6-p-tolylsulfinyltricycle<4.2.1.0^3,7>nonane-9-carboxylate 
• 139237-40-4 (S₁,S₂,R₃,R₄,S_S)-3-methoxycarbonyl-2-p-tolylsulfinylbicycle<2.2.1>hept-5-ene-2-carboxylic acid 
• 139118-94-8 (R₁,R₂,S₃,S₄,S_S)-3-methoxycarbonyl-2-p-tolylsulfinylbicycle<2.2.1>hept-5-ene-2-carboxylic acid 

Relevant articles and documents

Synthesis and Diels-Alder reactions of t-butyl and t-butyl, methyl (S)s-2-p-tolylsulfinylmaleates, chiral synthetic equivalents of monoalkyl and mixed dialkyl acetylenedicarboxylates

The reaction of t-butyl p-tolylsulfinylacetate with glyoxylic acid yielded maleate monoester 1, whose methylation afforded asymmetric diester 2. Conditions in which 1 and 2 react with cyclopentadiene exhibiting high facial and endo selectivities are reported.

SYNTHESIS AND DIELS-ALDER REACTIONS OF HOMOCHIRAL 2-SULFINYLMALEATES WITH CYCLOPENTADIENE

Enantiomerically pure 2-p-tolylsulfinylmaleates 1, 2 and 3 have been readily prepared by Knoevenagel reaction between (S)-menthyl p-toluenesulfinate and glyoxylic acid.Their asymmetric Diels-Alder reactions with cyclopentadiene have been studied under a wide range of uncatalyzed and catalyzed conditions and the stereochemical results have been explained by assuming a steric control approach, in term of S-cis or S-trans favoured conformations.Uncatalyzed Diels-Alder reactions of 1 and some Lewis acid catalyzed Diels-Alder reactions of 2 show high facial and endo selectivities.The facial selectivity of dienophile 2 highly depends on the Lewis acid, whereas reactivity of 1 and 3 is very sensitive to the solvent.These sulfinylmaleates 1, 2 and 3 act as synthetic equivalents of chiral acetylenedicarboxylates in Diels-Alder reactions after basic elimination of the sulfinylic moiety in the resulting adducts.