(S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate

Base Information

• Chemical Name: (S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate
• CAS No.: 1351987-26-2
• Molecular Formula: C₁₈H₂₄O₅
• Molecular Weight: 320.386
• Mol file: 1351987-26-2.mol

Synonyms:(S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate

Chemical Property of (S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate

There total 5 articles about (S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate 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:

(S)-3-(benzyloxycarbonyl)-4-methylpentanoic acid (134807-39-9) + ethyl potassium malonate (6148-64-7) → (S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate (1351987-26-2)

Guidance literature:

ethyl potassium malonate; With magnesium chloride; In tetrahydrofuran; at 20 - 22 ℃;

(S)-3-(benzyloxycarbonyl)-4-methylpentanoic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 0 ℃; for 15h; Reflux;

DOI:10.1002/adsc.201200934

Reference yield:

(S)-3-(benzyloxycarbonyl)-4-methylpentanoic acid (134807-39-9) + magnesium bis(3-ethoxy-3-oxopropanoate) (37517-78-5) → (S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate (1351987-26-2)

Guidance literature:

(S)-3-(benzyloxycarbonyl)-4-methylpentanoic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

magnesium bis(3-ethoxy-3-oxopropanoate); In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.oprd.5b00396

Reference yield:

(S)-1-benzyl-4-tert-butyl-2-isopropylsuccinate (134807-38-8) → (S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate (1351987-26-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 20 °C / Inert atmosphere

2.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0 °C / Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

With 1,1'-carbonyldiimidazole; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.oprd.5b00396

upstream raw materials:

(S)-1-benzyl-4-tert-butyl-2-isopropylsuccinate

(S)-3-(benzyloxycarbonyl)-4-methylpentanoic acid

ethyl potassium malonate

(S)-4-benzyl-3-(3-methylbutanoyl)oxazolidin-2-one

Downstream raw materials:

(2R,S)(5S)-6-benzyl 1-ethyl 5-isopropyl-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-3-oxohexanedioate

Refernces

• 1、 Arena, Giada,Barreca, Giuseppe,Carcone, Luca,Cini, Elena,Marras, Giovanni,Nedden, Hans G.,Rasparini, Marcello,Roseblade, Stephen,Russo, Adele,Taddei, Maurizio,Zanotti-Gerosa, Antonio. "Rhodium-catalyzed enantioselective hydrogenation of (E)-enol acetate acids". supporting information. p. 1449 - 1454. Retrieved 2013/06/27.