(4S,5S)-4-benzyl-3-(tert-butyloxy)carbonyl-2-oxooxazolidin-5-(E)-propenoic acid

Base Information

• Chemical Name: (4S,5S)-4-benzyl-3-(tert-butyloxy)carbonyl-2-oxooxazolidin-5-(E)-propenoic acid
• CAS No.: 178391-12-3
• Molecular Formula: C₁₈H₂₁NO₆
• Molecular Weight: 347.368
• Mol file: 178391-12-3.mol

Synonyms:(4S,5S)-4-benzyl-3-(tert-butyloxy)carbonyl-2-oxooxazolidin-5-(E)-propenoic acid

Chemical Property of (4S,5S)-4-benzyl-3-(tert-butyloxy)carbonyl-2-oxooxazolidin-5-(E)-propenoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-benzyl-3-(tert-butyloxy)carbonyl-2-oxooxazolidin-5-(E)-propenoic acid

There total 6 articles about (4S,5S)-4-benzyl-3-(tert-butyloxy)carbonyl-2-oxooxazolidin-5-(E)-propenoic acid 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: 74.0%

di-tert-butyl dicarbonate (24424-99-5) + (E)-3-((4S,5S)-4-Benzyl-2-oxo-oxazolidin-5-yl)-acrylic acid (178391-13-4) → (4S,5S)-4-benzyl-3-(tert-butyloxy)carbonyl-2-oxooxazolidin-5-(E)-propenoic acid (178391-12-3)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; at 60 ℃; for 12h;

DOI:10.1248/cpb.44.948

Reference yield:

(4S,5S)-4-benzyl-5-((E)-3-hydroxy-1-propenyl)oxazolidin-2-one (178391-11-2) → (4S,5S)-4-benzyl-3-(tert-butyloxy)carbonyl-2-oxooxazolidin-5-(E)-propenoic acid (178391-12-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Jones reagent / acetone / 0.25 h / Ambient temperature

2: 74 percent / Et₃N, 4-dimethylaminopyridine / tetrahydrofuran / 12 h / 60 °C

With dmap; jones reagent; triethylamine; In tetrahydrofuran; acetone;

DOI:10.1248/cpb.44.948

Reference yield:

Benzyl-((E)-(S)-1-benzyl-penta-2,4-dienyl)-carbamic acid methyl ester (178458-31-6) → (4S,5S)-4-benzyl-3-(tert-butyloxy)carbonyl-2-oxooxazolidin-5-(E)-propenoic acid (178391-12-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / I₂, KI / CH₂Cl₂ / 12 h / Ambient temperature

2: 91 percent / AcOH / dimethylformamide / 1.5 h / Ambient temperature

3: 73 percent / aq. NaOH / methanol / 1 h / Ambient temperature

4: 94 percent / Li, NH₃ (liq.) / tetrahydrofuran / 0.17 h / -78 °C

5: 84 percent / Jones reagent / acetone / 0.25 h / Ambient temperature

6: 74 percent / Et₃N, 4-dimethylaminopyridine / tetrahydrofuran / 12 h / 60 °C

With dmap; sodium hydroxide; jones reagent; ammonia; iodine; lithium; acetic acid; triethylamine; potassium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.44.948

upstream raw materials:

di-tert-butyl dicarbonate

(E)-3-((4S,5S)-4-Benzyl-2-oxo-oxazolidin-5-yl)-acrylic acid

(4S,5S)-4-benzyl-5-((E)-3-hydroxy-1-propenyl)oxazolidin-2-one

Benzyl-((E)-(S)-1-benzyl-penta-2,4-dienyl)-carbamic acid methyl ester