73803-23-3

Upstream product

• 557-20-0 diethylzinc 
• 99930-83-3 (R)-ethynyl-p-tolyl-sulfoxide 
• 123-38-6 propionaldehyde 
• 63268-43-9 (+)-(S)-dimethyl-p-tolylsulfinylmethanephosphonate 

Downstream Products

• 30506-35-5 (R)-1-(butylsulfinyl)-4-methylbenzene 
• 364781-27-1 (S)-2-((R)-Toluene-4-sulfinylmethyl)-butyronitrile 
• 204073-95-0 (+)-(2S)-(3Z,5E)-1-phenyl-7-(p-tolylsulfonyl)hepta-3,5-dien-2-ol 
• 198987-18-7 (-)-(2S,S_S)-(3Z,5E)-1-phenyl-7-(p-tolylsulfinyl)hepta-3,5-dien-2-ol 
• 198987-21-2 (+)-(2R,S_S)-(3E,5E)-1-phenyl-7-(p-tolylsulfinyl)hepta-3,5-dien-2-ol 
• 198987-11-0 (+)-(2R,3S,S_S)-(4E)-2-chloro-1-phenyl-4-(p-tolylsulfinyl)hept-4-en-3-ol 

Relevant academic research and scientific papers

Highly stereoselective synthesis of functionalized β,β-di- and trisubstituted vinylic sulfoxides by cu-catalyzed conjugate addition of organozinc reagents

β,β-Disubstituted chiral vinylic sulfoxides bearing functionalities have been synthesized via Cu-catalyzed conjugate addition of organozinc reagents to chiral 1-alkynyl sulfoxides. Due to the availability of functionalized organozinc reagents and high syn

Geometrically selective synthesis of functionalized β,β -disubstituted vinylic sulfoxides by Cu-catalyzed conjugate addition of organozinc reagents to 1-alkynyl sulfoxides

(Matrix presented) A new synthetic method of chiral β,β -disubstituted vinylic sulfoxides bearing various functionalities has been developed by employing Cu-catalyzed conjugate addition of an organozinc reagent to chiral 1-alkynyl sulfoxide. Since the reaction proceeds with very high syn-selectivity, both geometric β,β-disubstituted vinylic sulfoxides were stereoselectively synthesized by changing the combination of 1-alkynyl sulfoxide and the organozinc reagent.

Synthesis of deuterium-labeled plant sterols and analysis of their side-chain mobility by solid state deuterium NMR

The plant sterols sitosterol and stigmasterol exert very different effects on plant model membranes, the first one being a 'reinforcer' like cholesterol, the second one not. 25-2H-Stigmasterol has been synthesized by coupling of the 22-aldehyde derived from stigmasterol by ozonolysis, with the proper sulfone labeled in position 25. The configuration of the ethyl side chain at C-24 was controlled by separation of the diastereomers introduced via a chiral sulfoxide. This synthetic scheme allowed the introduction of a labeled side chain in plant sterols in eight steps for stigmasterol and nine for sitosterol (overall yield ca. 15%). Using both diastereomers, the 24-epimers of sitosterol (clionasterol) and stigmasterol (poriferasterol) have also been synthesized. Deuterium NMR on oriented lipid bilayers made of soybean phosphatidylcholine and containing these four labeled plant sterols clearly reveals the difference of orientation and mobility of the four side chains.

Stereoselective Synthesis of Alcohols, II Stereochemistry of the Sigmatropic Rearrangement of 3-Substituted 2-Alkenyl Sulfoxides

Rearrangement of the 3-E-substituted allyl sulfoxides 5 to the allyl alcohols 19 and 30 proceeds with low enantiomeric selectivity.In contrast, the 3-Z-substituted allyl sulfoxide 7b rearranged uniformly via the endo-transition state 26.