198218-59-6

Basic information

• Product Name: S-ethyl (2R,3S,4E)-2-(tert-butyldimethylsiloxy)-3-hydroxy-5-phenyl-4-pentenethioate
• CAS NO: 198218-59-6
• Molecular Weight: 366.597
• Mol File: 198218-59-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: S-ethyl (2R,3S,4E)-2-(tert-butyldimethylsiloxy)-3-hydroxy-5-phenyl-4-pentenethioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-ethyl (2R,3S,4E)-2-(tert-butyldimethylsiloxy)-3-hydroxy-5-phenyl-4-pentenethioate(198218-59-6)
• EPA Substance Registry System: S-ethyl (2R,3S,4E)-2-(tert-butyldimethylsiloxy)-3-hydroxy-5-phenyl-4-pentenethioate(198218-59-6)

Safety Data

• Hazardous Substances Data: 198218-59-6(Hazardous Substances Data)

Upstream product

• 160114-64-7 S-ethyl 2-(t-butyldimethylsiloxy)ethanethioate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 105459-05-0 {[tert-butyl(dimethyl)silyl]oxy}acetic acid 
• 78826-45-6 2-((tert-butyldimethylsilyl)oxy)acetyl chloride 
• 67226-76-0 (tert-butyldimethylsiloxy) acetic acid tert-butyldimethylsilyl ester 
• 67226-78-2 ethyl 2-(tert-butyldimethylsilyloxy)acetate 
• 14371-10-9 (E)-3-phenylpropenal 
• 138509-94-1 (Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene 

Relevant articles and documents

Highly Enantioselective Synthesis of syn-α,β-Dihydroxy Thioesters by the Asymmetric Aldol Reaction Using a Chiral Tin(II) Lewis Acid

syn-α,β-Dihydroxy thioesters are prepared in good yields with high diastereo- and enantioselectivities by the asymmetric aldol reaction of 1-trimethylsiloxy-1-ethylthio-2-t-butyldimethylsiloxyethene with aldehydes using a chiral promoter consisting of tin(II) triflate, a chiral diamine and dibutyltin diacetate.

Enantioselective synthesis of both diastereomers including the α-alkoxy-β-hydroxy-β-methyl(phenyl) units, by chiral tin(II) Lewis acid-mediated asymmetric aldol reactions

Diastereo- and enantioselective synthesis of both diasteromers, including the α-alkoxy-β-hydroxy-β-methyl(phenyl) units, was performed by using chiral tin(II) Lewis acid-mediated asymmetric aldol reactions of α-alkoxy silyl enol ethers with α-ketoesters. (S)-1-Propyl-2-[(1,2,3,4-tetrahydroisoquinolinyl))methyl]pyrrolidine (13), a new type of chiral diamine, was found to be effective as a chiral source in these reactions and also in the reactions of 2-(t-butyldimethylsiloxy)-1-ethylthio-1-(trimethylsiloxy)ethene (9) with aldehydes for the synthesis of optically active syn-α,β-dihydroxy thioester derivatives. (-)-2-C-Methyl-D-erythrono-1,4-lactone and (+)-2-C-methyl-L-threono-1,4-lactone were synthesized by using these reactions.