(E)-(S)-7-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-7-oxo-hept-5-enal

Base Information

• Chemical Name: (E)-(S)-7-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-7-oxo-hept-5-enal
• CAS No.: 861899-34-5
• Molecular Formula: C₁₈H₂₁NO₄
• Molecular Weight: 315.369
• Mol file: 861899-34-5.mol

Synonyms:(E)-(S)-7-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-7-oxo-hept-5-enal

Chemical Property of (E)-(S)-7-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-7-oxo-hept-5-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-7-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-7-oxo-hept-5-enal

There total 7 articles about (E)-(S)-7-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-7-oxo-hept-5-enal 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-benzyl-3-((S,E)-7-hydroxy-6-methylhept-2-enoyl)oxazolidin-2-one (861899-32-3) → (E)-(S)-7-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-7-oxo-hept-5-enal (861899-34-5)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2005.05.004

Reference yield:

(E)-(S)-5-(4-Methoxy-benzyloxy)-4-methyl-pent-2-enoic acid ethyl ester (361543-13-7) → (E)-(S)-7-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-7-oxo-hept-5-enal (861899-34-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / H₂ / Pd/C / methanol / 20 °C

2: diisobutylaluminum hydride / CH₂Cl₂ / 30 h / -78 °C

3: 85 percent / LiCl; DIPEA / acetonitrile / 20 h / 20 °C

4: 92 percent / aq. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 2 h / 20 °C

5: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2005.05.004

Reference yield:

(S)-5-(4-methoxybenzyloxy)-4-methylpentanal (861899-24-3) → (E)-(S)-7-((R)-4-Benzyl-2-oxo-oxazolidin-3-yl)-2-methyl-7-oxo-hept-5-enal (861899-34-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / LiCl; DIPEA / acetonitrile / 20 h / 20 °C

2: 92 percent / aq. 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 2 h / 20 °C

3: 92 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.5 h / 20 °C

With pyridine; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2005.05.004

upstream raw materials:

(R)-4-benzyl-3-((S,E)-7-hydroxy-6-methylhept-2-enoyl)oxazolidin-2-one

(S)-5-(4-methoxybenzyloxy)-4-methylpentanal

(E)-(S)-5-(4-Methoxy-benzyloxy)-4-methyl-pent-2-enoic acid ethyl ester

(S)-5-(4-Methoxy-benzyloxy)-4-methyl-pentanoic acid ethyl ester

Downstream raw materials:

(R)-3-((S,2E,7E,9E)-11-(4-methoxybenzyloxy)-6-methylundeca-2,7,9-trienoyl)-4-benzyloxazolidin-2-one