(2R)-2-pentylbutanedioic acid

Base Information

• Chemical Name: (2R)-2-pentylbutanedioic acid
• CAS No.: 3975-91-5
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.224
• Mol file: 3975-91-5.mol

Synonyms:(R)-(+)-2-pentylsuccinic acid

Chemical Property of (2R)-2-pentylbutanedioic acid

Chemical Property:

• Vapor Pressure: 0.000336mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-2-pentylbutanedioic acid

There total 14 articles about (2R)-2-pentylbutanedioic acid 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: 52.0%

(2R)-2-<(2,2,2-trichloroethoxycarbonyl)methyl>heptanoic acid (147961-57-7) → (R)-(+)-2-pentylsuccinic acid (3975-91-5)

Guidance literature:

With ammonium acetate; zinc; In tetrahydrofuran; water; for 3h; Ambient temperature;

DOI:10.7164/antibiotics.47.1481

Reference yield:

monoamyl succinic acid (3507-62-8) → (R)-(+)-2-pentylsuccinic acid (3975-91-5)

Guidance literature:

With strychnine salt;

Reference yield:

(4S)-4-isopropyl-3-(1-oxoheptyl)-2-oxazolidinone (145588-98-3) → (R)-(+)-2-pentylsuccinic acid (3975-91-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 0.59M LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 5.5 h

2: 1.) 1.65M BuLi / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, hexane, 1 h

3: 838 mg / 4N HCl / dioxane / Ambient temperature

4: oxalyl chloride / benzene / 2 h / 60 °C

5: pyridine / tetrahydrofuran / 1.5 h / -15 °C

6: H₂ / 10percent Pd/C / methanol / 2 h / Ambient temperature

7: 52 percent / 1M NH₄OAc, Zn / tetrahydrofuran; H₂O / 3 h / Ambient temperature

With pyridine; hydrogenchloride; n-butyllithium; oxalyl dichloride; ammonium acetate; hydrogen; zinc; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water; benzene;

DOI:10.7164/antibiotics.47.1481

upstream raw materials:

monoamyl succinic acid

N⁴-hydroxy-N¹-[2-methyl-1-(morpholine-4-carbonyl)-propyl]-2-pentyl-succinamide

actinonin

(R)-3-[(2R,3R)-5-Hydroxy-7-methoxy-2,3-dimethyl-8-(3-methyl-but-2-enyl)-4-oxo-chroman-6-yl]-octanoic acid

Downstream raw materials:

monoamyl succinic acid

Refernces

• 1、 Tamaki,Ogita,Tanzawa,Sugimura. "Synthesis and determination of the absolute configuration of matlystatin B". . p. 683 - 686. Retrieved 2007/10/02.
• 2、 Devlin,Ollis,Thorpe,Wood,Broughton,Warren,Wooldridge,Wright. "Studies concerning the antibiotic actinonin. Part III. Synthesis structural analogues of actinonin by the anhydride-imide method.". . p. 830 - 841. Retrieved 2007/10/04.