(R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]oxazolidin-2-one

Base Information

• Chemical Name: (R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]oxazolidin-2-one
• CAS No.: 886733-93-3
• Molecular Formula: C₁₈H₂₁NO₃
• Molecular Weight: 299.37
• Mol file: 886733-93-3.mol

Synonyms:(R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]oxazolidin-2-one

Chemical Property of (R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]oxazolidin-2-one

There total 5 articles about (R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]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: 92.0%

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) + (2E,4E)-2,4-dimethylhexa-2,4-dienoic acid (241806-94-0) → (R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]oxazolidin-2-one (886733-93-3)

Guidance literature:

(2E,4E)-2,4-dimethylhexa-2,4-dienoic acid; With pivaloyl chloride; triethylamine; In tetrahydrofuran; at -15 ℃; for 0.25h; Inert atmosphere;

(R)-4-(phenylmethyl)-2-oxazolidinone; With lithium chloride; In tetrahydrofuran; at -15 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.01.054

Reference yield:

C13H20O3 + (R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) → (R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]oxazolidin-2-one (886733-93-3)

Guidance literature:

With lithium chloride; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2006.02.058

Reference yield:

2-methylbut-2-enal (497-03-0) → (R)-4-benzyl-3-[(2E,4E)-2,4-dimethylhexa-2,4-dienoyl]oxazolidin-2-one (886733-93-3)

Guidance literature:

Multi-step reaction with 4 steps

1: tBuOLi / hexane / 20 °C

2: aq. NaOH / ethanol / 50 °C

3: Et₃N / tetrahydrofuran / -15 °C

4: LiCl / tetrahydrofuran / 20 °C

With sodium hydroxide; triethylamine; lithium chloride; lithium tert-butoxide; In tetrahydrofuran; ethanol; hexane; 1: Horner-Wadsorth-Emmon reaction;

DOI:10.1016/j.tetlet.2006.02.058

upstream raw materials:

(R)-4-(phenylmethyl)-2-oxazolidinone

2-methylbut-2-enal

ethyl (2E,4E)-2,4-dimethylhexa-2,4-dienoate

(2E,4E)-2,4-dimethylhexa-2,4-dienoic acid

Downstream raw materials:

(+)-thiolactomycin

(R,E)-benzyl 2-(3,3-dimethoxypropylthio)-2,4-dimethylhexa-3,5-dienoate

(R,E)-benzyl 2,4-dimethyl-2-(propionylthio)hexa-3,5-dienoate

(R,E)-benzyl 2,4-dimethyl-2-(3-oxopropylthio)hexa-3,5-dienoate