methyl (3R,αR)-3--2-oxo-3-phenylpropionate

Base Information

• Chemical Name: methyl (3R,αR)-3--2-oxo-3-phenylpropionate
• CAS No.: 161453-16-3
• Molecular Formula: C₂₅H₂₅NO₃
• Molecular Weight: 387.478
• Mol file: 161453-16-3.mol

Synonyms:

Chemical Property of methyl (3R,αR)-3--2-oxo-3-phenylpropionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3R,αR)-3--2-oxo-3-phenylpropionate

There total 8 articles about methyl (3R,αR)-3--2-oxo-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:

lithium benzyl-(R)-1-phenylethylamide → methyl (3R,αR)-3--2-oxo-3-phenylpropionate (161453-16-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) (+)-(camphorsulfonyl)oxaziridine / 1) THF, -78 deg C, 2 h; 2) THF, -78 deg C (1 h), -78 --> 0 deg C (15 min)

2: 87 percent / trifluoroacetic acid / CH₂Cl₂ / Ambient temperature

3: 99 percent / diethyl ether / 1) 0 deg C, 15 min; 2) room temperature, 15 min

4: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Et₃N / 1) CH₂Cl₂, -60 deg C (2 min), -10 deg C (30 min); 2) CH₂Cl₂, -10 deg C (5 min), room temperature, 1.5 h

With oxalyl dichloride; (+)-(2S,8aS)-(camphorylsulfonyl)oxaziridine; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In diethyl ether; dichloromethane;

Reference yield:

tert-butyl cinnamate (14990-09-1) → methyl (3R,αR)-3--2-oxo-3-phenylpropionate (161453-16-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 2.) (+)-(camphorsulfonyl)oxaziridine / 1) THF, -78 deg C, 2 h; 2) THF, -78 deg C (1 h), -78 --> 0 deg C (15 min)

2: 87 percent / trifluoroacetic acid / CH₂Cl₂ / Ambient temperature

3: 99 percent / diethyl ether / 1) 0 deg C, 15 min; 2) room temperature, 15 min

4: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Et₃N / 1) CH₂Cl₂, -60 deg C (2 min), -10 deg C (30 min); 2) CH₂Cl₂, -10 deg C (5 min), room temperature, 1.5 h

With oxalyl dichloride; (+)-(2S,8aS)-(camphorylsulfonyl)oxaziridine; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In diethyl ether; dichloromethane;

Reference yield:

tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate (151671-03-3) → methyl (3R,αR)-3--2-oxo-3-phenylpropionate (161453-16-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / trifluoroacetic acid / CH₂Cl₂ / Ambient temperature

2: 99 percent / diethyl ether / 1) 0 deg C, 15 min; 2) room temperature, 15 min

3: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) Et₃N / 1) CH₂Cl₂, -60 deg C (2 min), -10 deg C (30 min); 2) CH₂Cl₂, -10 deg C (5 min), room temperature, 1.5 h

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In diethyl ether; dichloromethane;

upstream raw materials:

tert-butyl cinnamate

Methyl cinnamate

tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate

tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

Downstream raw materials:

methyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate