3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one

Base Information

• Chemical Name: 3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one
• CAS No.: 790697-94-8
• Molecular Formula: C₁₉H₂₄BrNO₅
• Molecular Weight: 426.307
• Mol file: 790697-94-8.mol

Synonyms:3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one

Chemical Property of 3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one

There total 1 articles about 3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one 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: 71.0%

2-bromo-3-iodo-1-propene (111036-04-5) + (R)-(+)-[4-isopropyl-3-(4-methoxybenzyloxy)acetyl]-2-oxazolidinone → 3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one (790697-94-8)

Guidance literature:

(R)-(+)-[4-isopropyl-3-(4-methoxybenzyloxy)acetyl]-2-oxazolidinone; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

2-bromo-3-iodo-1-propene; In tetrahydrofuran; at -78 - -45 ℃;

DOI:10.1021/ja0455852

Reference yield: 92.0%

3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one (790697-94-8) → (S)-4-Bromo-2-(4-methoxy-benzyloxy)-pent-4-en-1-ol (790698-12-3)

Guidance literature:

3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one; With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 1h;

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/ja0455852

Reference yield:

3-[4-bromo-2-(R)-(4-methoxy-benzyloxy)-pent-4-enoyl]-4-(R)-isopropyl-oxazolidin-2-one (790697-94-8) → (S)-2-(4-Methoxy-benzyloxy)-3-((S)-5-methyl-2-oxo-2,5-dihydro-furan-3-yl)-propionaldehyde

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium borohydride / tetrahydrofuran / 1 h / 20 °C

1.2: 92 percent / aq. NaOH / tetrahydrofuran / 0.5 h / 20 °C

2.1: 72 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

3.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C

3.2: 82 percent / tetrahydrofuran; pentane / 3 h / 20 °C

4.1: PPh₃ / tetrahydrofuran / 0.17 h / 20 °C

4.2: 87 percent / DEAD / tetrahydrofuran / 2 h

5.1: CH₂Cl₂ / 0.5 h

5.2: 95 percent / Cl₂(Cy₃P)(IMes)Ru=CHPh / CH₂Cl₂ / 14 h / Heating

6.1: 94 percent / 3HF*NEt₃ / acetonitrile / 72 h / 20 °C

7.1: 0.414 g / oxalyl chloride; dimethylsulfoxide; DIEA / CH₂Cl₂ / 0.25 h / -78 - 0 °C

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; tert.-butyl lithium; dimethyl sulfoxide; triethylamine tris(hydrogen fluoride); N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile; pentane; 4.1: Mitsunobu reaction;

DOI:10.1021/ja0455852

upstream raw materials:

2-bromo-3-iodo-1-propene

Downstream raw materials:

(S)-4-Bromo-2-(4-methoxy-benzyloxy)-pent-4-en-1-ol

(+)-gigantecin

3-[3-hydroxy-2-(4-methoxy-benzyloxy)propyl]-5-methyl-5H-furan-2-one

3-[4-iodo-2-(4-methoxy-benzyloxy)but-3-enyl]-5-methyl-5H-furan-2-one