ethyl (2S,3R)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate

Base Information

• Chemical Name: ethyl (2S,3R)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate
• CAS No.: 285565-00-6
• Molecular Formula: C₁₂H₁₅BrO₃
• Molecular Weight: 287.153
• Mol file: 285565-00-6.mol

Synonyms:ethyl (2S,3R)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate

Chemical Property of ethyl (2S,3R)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,3R)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate

There total 2 articles about ethyl (2S,3R)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate 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:

benzaldehyde (100-52-7) + 2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene (153645-08-0) → (2S,3S)-2-Bromo-3-hydroxy-2-methyl-3-phenyl-propionic acid ethyl ester (141320-55-0,142612-26-8) + ethyl (2S,3R)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate (285565-00-6) + ethyl (2R,3S)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate

Guidance literature:

With N-(p-toluenesulfonyl)-L-valine; borane-THF; In tetrahydrofuran; dichloromethane; at -78 ℃; for 15h; Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(00)00089-6

Reference yield:

benzaldehyde (100-52-7) + Ethyl 2-bromopropionate (535-11-5,41978-69-2) → ethyl (2S,3R)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate (285565-00-6) + ethyl (2R,3R)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate + ethyl (2R,3S)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate + ethyl (2S,3S)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate

Guidance literature:

Ethyl 2-bromopropionate; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.25h;

With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - 20 ℃;

benzaldehyde; With N-(p-toluenesulfonyl)-L-valine; borane-THF; In dichloromethane; at -78 ℃; for 15h; Title compound not separated from byproducts;

DOI:10.1016/j.tetasy.2003.06.005

Reference yield: 86.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + ethyl (2S,3R)-2-bromo-3-hydroxy-2-methyl-3-phenylpropionate (285565-00-6) → (2S,3R)-2-Bromo-2-methyl-3-phenyl-3-trimethylsilanyloxy-propionic acid ethyl ester (370868-13-6)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 20 ℃;

DOI:10.1246/bcsj.74.1485

upstream raw materials:

benzaldehyde

2-bromo-1-ethoxy-2-methyl-1-trimethylsilyoxyethene

Ethyl 2-bromopropionate

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

(1R,2R)-2-Bromo-2-methyl-1-phenyl-propane-1,3-diol

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