(R)-benzyl 2-benzyl-3-oxopentanoate

Base Information

• Chemical Name: (R)-benzyl 2-benzyl-3-oxopentanoate
• CAS No.: 1401455-66-0
• Molecular Formula: C₁₉H₂₀O₃
• Molecular Weight: 296.366
• Mol file: 1401455-66-0.mol

Synonyms:(R)-benzyl 2-benzyl-3-oxopentanoate

Chemical Property of (R)-benzyl 2-benzyl-3-oxopentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (R)-benzyl 2-benzyl-3-oxopentanoate

There total 3 articles about (R)-benzyl 2-benzyl-3-oxopentanoate 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%

2-diazo-3-phenylpropanoic acid benzyl ester (126191-07-9) + propionaldehyde (123-38-6) → C14H18O3 (1401455-81-9) + (R)-benzyl 2-benzyl-3-oxopentanoate (1401455-66-0)

Guidance literature:

With C₂HF₆NO₄S₂*C₃₁H₃₂BNO; In toluene; at -95 ℃; for 2h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201204350

Reference yield:

benzyl acetoacetate (5396-89-4) → (R)-benzyl 2-benzyl-3-oxopentanoate (1401455-66-0)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride / tetrahydrofuran; mineral oil / 0 °C / Reflux; Inert atmosphere

2: 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 0 - 20 °C / Inert atmosphere

3: C₂HF₆NO₄S₂*C₃₁H₃₂BNO / toluene / 2 h / -95 °C / Inert atmosphere

With 4-acetamidobenzenesulfonyl azide; C₂HF₆NO₄S₂*C₃₁H₃₂BNO; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; toluene; acetonitrile; mineral oil; 3: Roskamp reaction;

DOI:10.1002/anie.201204350

Reference yield:

2-benzyl-3-oxobutyric acid benzyl ester → (R)-benzyl 2-benzyl-3-oxopentanoate (1401455-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-acetamidobenzenesulfonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 24 h / 0 - 20 °C / Inert atmosphere

2: C₂HF₆NO₄S₂*C₃₁H₃₂BNO / toluene / 2 h / -95 °C / Inert atmosphere

With 4-acetamidobenzenesulfonyl azide; C₂HF₆NO₄S₂*C₃₁H₃₂BNO; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; acetonitrile; 2: Roskamp reaction;

DOI:10.1002/anie.201204350

upstream raw materials:

benzyl acetoacetate

2-diazo-3-phenylpropanoic acid benzyl ester

propionaldehyde