138509-96-3

Basic information

• Product Name: S-ethyl (2R,3R)-2-(t-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate
• CAS NO: 138509-96-3
• Molecular Weight: 340.559
• Mol File: 138509-96-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: S-ethyl (2R,3R)-2-(t-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate(CAS DataBase Reference)
• NIST Chemistry Reference: S-ethyl (2R,3R)-2-(t-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate(138509-96-3)
• EPA Substance Registry System: S-ethyl (2R,3R)-2-(t-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate(138509-96-3)

Safety Data

• Hazardous Substances Data: 138509-96-3(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 138509-94-1 (Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene 
• 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 

Relevant articles and documents

Diastereo- and Enantioselective Synthesis of syn- and anti-1,2-Diol Units by Asymmetric Aldol Reactions

syn- and anti-1,2-Diol units were prepared by using asymmetric aldol reactions of the silyl enol ethers derived from α-alkoxythioacetic S-esters with aldehydes.In the presence of tin(II) triflate, a chiral diamine, and dibutyltin diacetate, (Z)-2-benzyloxy-1-ethylthino-1-(trimethylsiloxy)ethene reacted with aldehydes to afford the corresponding anti-aldol adducts in high yields with excellent diastereo- and enantioselectivities, while syn-adducts were obtained from (Z)-2-(t-butyldimethylsiloxy)-1-ethylthio-1-(trimethylsiloxy)ethene and aldehydes under the same reaction conditions.Thus, both diastereomers can be synthesized in excellent enantiomeric excesses by simply choosing the protective groups of the alkoxyl parts of the silyl enol ethers.

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.