S-ethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

Base Information

• Chemical Name: S-ethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate
• CAS No.: 159573-36-1
• Molecular Formula: C₁₇H₂₈O₃SSi
• Molecular Weight: 340.559
• Mol file: 159573-36-1.mol

Synonyms:S-ethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

Chemical Property of S-ethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-ethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

There total 15 articles about S-ethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

benzaldehyde (100-52-7) + (Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene (138509-94-1) → S-ethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate (159573-36-1)

Guidance literature:

With tin(II) trifluoromethanesulfonate; chiral N-methyl-2-<(N'-2,3-dihydroindolyl)methylene>pyrrolidine; dibutyltin diacetate; In dichloromethane; at -78 ℃; for 21h;

DOI:10.1021/ja00100a078

Reference yield:

benzaldehyde (100-52-7) + (Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene (138509-94-1) → S-ethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate (159573-36-1) + (anti)-S-ethyl 2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate

Guidance literature:

With tin(II) trifluoromethanesulfonate; dibutyltin diacetate; (S)-1-methyl-2-[(indolinyl)methyl]pyrrolidine; In dichloromethane; at -78 ℃; for 21h; Yield given. Yields of byproduct given;

DOI:10.1002/chem.19970030914

Reference yield:

benzaldehyde (100-52-7) + (Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene (138509-94-1) → S-ethyl (2S,3R)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate (138509-95-2) + S-ethyl (2R,3R)-2-(t-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate (138509-96-3) + S-ethyl (2R,3S)-2-(tert-butyldimethylsiloxy)-3-hydroxy-3-phenylpropanethioate (159573-36-1)

Guidance literature:

With tin(II) trifluoromethanesulfonate; dibutyltin diacetate; (S)-1-Ethyl-2-<(piperidin-1-yl)methyl>pyrrolidine; In dichloromethane; at -78 ℃; for 20h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1246/bcsj.67.1708

upstream raw materials:

benzaldehyde

(Z)-1-(ethylthio)-1-(trimethylsiloxy)-2-(tert-butyldimethylsiloxy)ethene

ethyl 2-(tert-butyldimethylsilyloxy)acetate

(tert-butyldimethylsiloxy) acetic acid tert-butyldimethylsilyl ester