ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate

Base Information

• Chemical Name: ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate
• CAS No.: 212136-31-7
• Molecular Formula: C₁₃H₁₈O₃S
• Molecular Weight: 254.35
• Mol file: 212136-31-7.mol

Synonyms:ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate

Chemical Property of ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate

There total 4 articles about ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate 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: 80.0%

benzaldehyde (100-52-7) + (E/Z)-1-ethoxy-1-(trimethylsiloxy)-2-methylthiopropene (1051925-20-2) → ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate (212136-31-7) + (2R,3R)-3-Hydroxy-2-methyl-2-methylsulfanyl-3-phenyl-propionic acid ethyl ester

Guidance literature:

With dibutyltin diacetate; Sn(OTf)2*chiral diamine; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1016/S0040-4039(01)01238-2

Reference yield:

2-methylsulfanyl-propionic acid ethyl ester (40800-76-8) → ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate (212136-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA

2: 80 percent / di-n-butyltin diacetate / Sn(OTf)2*chiral diamine / CH₂Cl₂ / 1 h / -78 °C

With dibutyltin diacetate; lithium diisopropyl amide; Sn(OTf)2*chiral diamine; In dichloromethane;

DOI:10.1016/S0040-4039(01)01238-2

Reference yield:

C16H26O3SSi → ethyl (2S,3R)-3-hydroxy-2-methyl-2-(methylthio)-3-phenylpropanoate (212136-31-7)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; EtCN;

DOI:10.1055/s-0029-1216922

upstream raw materials:

benzaldehyde

(E/Z)-1-ethoxy-1-(trimethylsiloxy)-2-methylthiopropene

2-methylsulfanyl-propionic acid ethyl ester

Downstream raw materials:

Ethyl (2S,3S)-3-hydroxy-2-methyl-3-phenylpropionic acid

(2R,3S)-3-hydroxy-2-methyl-3-phenyl-propionic acid ethyl ester