(4S)-3-[(2E,5S)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-2-one

Base Information

• Chemical Name: (4S)-3-[(2E,5S)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-2-one
• CAS No.: 794525-13-6
• Molecular Formula: C₁₈H₂₃NO₄
• Molecular Weight: 317.385
• Mol file: 794525-13-6.mol

Synonyms:(4S)-3-[(2E,5S)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-2-one

Chemical Property of (4S)-3-[(2E,5S)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-3-[(2E,5S)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-2-one

There total 2 articles about (4S)-3-[(2E,5S)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-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:

benzaldehyde (100-52-7) + (4S)-3-[(1E)-1-(tert-butyldimethylsilyloxy)-2-methylbuta-1,3-dienyl]-4-isopropyloxazolidin-2-one (303142-77-0) → (4S)-3-[(2E,5S)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-2-one (794525-13-6) + (4S)-3-[(2E,5R)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-2-one

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 6h; Title compound not separated from byproducts;

DOI:10.1021/ja0465855

Reference yield:

N-(2'-methyl-2'E-butanoyl)-4S-isopropyl-1,3-oxazolidin-2-one (136057-71-1) → (4S)-3-[(2E,5S)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-2-one (794525-13-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaHMDS / tetrahydrofuran / 1.5 h / -78 °C

1.2: 85 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: TiCl₄ / CH₂Cl₂ / 6 h / -78 °C

With sodium hexamethyldisilazane; titanium tetrachloride; In tetrahydrofuran; dichloromethane; 2.1: Mukaiyama reaction;

DOI:10.1021/ja0465855

Reference yield:

(4S)-3-[(2E,5S)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-2-one (794525-13-6) → (S)-3-hydroxy-3-phenyl-propionaldehyde (133271-05-3)

Guidance literature:

(4S)-3-[(2E,5S)-5-hydroxy-2-methyl-5-phenylpent-2-enoyl]-4-isopropyloxazolidin-2-one; With ozone;

With dimethylsulfide;

DOI:10.1021/ja0465855

upstream raw materials:

benzaldehyde

(4S)-3-[(1E)-1-(tert-butyldimethylsilyloxy)-2-methylbuta-1,3-dienyl]-4-isopropyloxazolidin-2-one

N-(2'-methyl-2'E-butanoyl)-4S-isopropyl-1,3-oxazolidin-2-one

Downstream raw materials:

(S)-3-hydroxy-3-phenyl-propionaldehyde

(S)-1-phenylpropane-1,3-diyl diacetate

(S)-3-phenyl-1,3-propanediol