Pentanoic acid, 2-methyl-4-oxo-, (2S)- (9CI)

Base Information

• Chemical Name: Pentanoic acid, 2-methyl-4-oxo-, (2S)- (9CI)
• CAS No.: 148493-16-7
• Molecular Formula: C6H10 O3
• Molecular Weight: 130.1418
• Mol file: 148493-16-7.mol

Synonyms:Pentanoicacid, 2-methyl-4-oxo-, (S)-

Chemical Property of Pentanoic acid, 2-methyl-4-oxo-, (2S)- (9CI)

Chemical Property:

• PSA: 54.37000
• LogP: 0.68620

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pentanoic acid, 2-methyl-4-oxo-, (2S)- (9CI)

There total 9 articles about Pentanoic acid, 2-methyl-4-oxo-, (2S)- (9CI) 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: 33.0%

methyl 2-methyl-4-oxo-pentanoate (32811-25-9) → (2R)-(+)-2-methyl-4-oxopentanoic acid (614759-21-6) + (2S)-(–)-2-methyl-4-oxopentanoic acid (148493-16-7) + (2R)-(+)-methyl 2-methyl-4-oxopentanoate

Guidance literature:

With Porcine Pancreas Lipase; sodium sulfate; In aq. phosphate buffer; at 32 ℃; for 10h; pH=7.2; Reagent/catalyst; enantioselective reaction; Catalytic behavior; Kinetics; Resolution of racemate; Enzymatic reaction;

DOI:10.1080/10242422.2018.1502274

Reference yield:

(2S)-(–)-methyl 2-methyl-4-oxopentanoate (440084-24-2) → (2S)-(–)-2-methyl-4-oxopentanoic acid (148493-16-7)

Guidance literature:

With lithium hydroxide; at 25 ℃; for 0.5h; Yield given;

DOI:10.1016/S0040-4039(00)60343-X

Reference yield:

(S)-2-Acetyl-3-methyl-succinic acid 1-tert-butyl ester 4-methyl ester (915768-07-9) → (2S)-(–)-2-methyl-4-oxopentanoic acid (148493-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / CH₂Cl₂ / 24 h / Ambient temperature

2: aq. LiOH / tetrahydrofuran / 0.5 h / Ambient temperature

With lithium hydroxide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00121a031

upstream raw materials:

(2S)-(–)-methyl 2-methyl-4-oxopentanoate

(S)-2-Acetyl-3-methyl-succinic acid 1-tert-butyl ester 4-methyl ester

methyl 2-methyl-4-nitropentanoate

methyl 2-methyl-4-oxo-pentanoate

Downstream raw materials:

(2S)-(–)-methyl 2-methyl-4-oxopentanoate

Refernces

• 1、 Ferreira, Edgard A.,Rodezno, Sindy V. A.,Omori, álvaro T.,Cunha, Rodrigo L. O. R.. "A study on the enzyme catalysed enantioselective hydrolysis of methyl 2-methyl-4-oxopentanoate, a precursor of chiral γ-butyrolactones". . p. 115 - 123. Retrieved 2019.