(4S,5R)-diisopropyl-3-(3-phenyl-2-(E)-propenoyl)-2-oxazolidinone

Base Information

• Chemical Name: (4S,5R)-diisopropyl-3-(3-phenyl-2-(E)-propenoyl)-2-oxazolidinone
• CAS No.: 215929-25-2
• Molecular Formula: C₁₈H₂₃NO₃
• Molecular Weight: 301.386
• Mol file: 215929-25-2.mol

Synonyms:

Chemical Property of (4S,5R)-diisopropyl-3-(3-phenyl-2-(E)-propenoyl)-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-diisopropyl-3-(3-phenyl-2-(E)-propenoyl)-2-oxazolidinone

There total 5 articles about (4S,5R)-diisopropyl-3-(3-phenyl-2-(E)-propenoyl)-2-oxazolidinone 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:

(2R,3R)-diisopropyloxirane (215929-21-8) → (4S,5R)-diisopropyl-3-(3-phenyl-2-(E)-propenoyl)-2-oxazolidinone (215929-25-2)

Guidance literature:

Multi-step reaction with 4 steps

1: LiN₃ / dimethylformamide / 24 h / 110 °C

2: 2.76 g / H₂ / Pd/C / ethanol / 5 h / Ambient temperature

3: 94 percent / Et₃N / CH₂Cl₂; toluene / 2 h / Ambient temperature

4: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 10 min; 2) THF, hexane, -78 deg C, 1 h, -78 deg C --> rt

With n-butyllithium; lithium azide; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo981259r

Reference yield:

(3R,4R)-2,5-dimethyl-3,4-hexanediol (115889-27-5) → (4S,5R)-diisopropyl-3-(3-phenyl-2-(E)-propenoyl)-2-oxazolidinone (215929-25-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) trimethyl orthoacetate, pyridinium toluenesulfonic acid, 2) AcBr, 3.) NaOH / 1) CH₂Cl₂, rt, 2 h; 2) CH₂Cl₂, 0 deg C --> rt, overnight; 3) ether, MeOH, rt, 24 h

2: LiN₃ / dimethylformamide / 24 h / 110 °C

3: 2.76 g / H₂ / Pd/C / ethanol / 5 h / Ambient temperature

4: 94 percent / Et₃N / CH₂Cl₂; toluene / 2 h / Ambient temperature

5: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 10 min; 2) THF, hexane, -78 deg C, 1 h, -78 deg C --> rt

With Trimethyl orthoacetate; sodium hydroxide; n-butyllithium; lithium azide; Acetyl bromide; pyridinium toluenesulfonic acid; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo981259r

Reference yield:

2,5-dimethyl-3S-azidohexan-4R-ol (215929-22-9) → (4S,5R)-diisopropyl-3-(3-phenyl-2-(E)-propenoyl)-2-oxazolidinone (215929-25-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.76 g / H₂ / Pd/C / ethanol / 5 h / Ambient temperature

2: 94 percent / Et₃N / CH₂Cl₂; toluene / 2 h / Ambient temperature

3: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 10 min; 2) THF, hexane, -78 deg C, 1 h, -78 deg C --> rt

With n-butyllithium; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; toluene;

DOI:10.1021/jo981259r

upstream raw materials:

Cinnamoyl chloride

(4S,5R)-diisopropyl-2-oxazolidinone

(2R,3R)-diisopropyloxirane

(3R,4R)-2,5-dimethyl-3,4-hexanediol