Pentanedioic acid, 3-phenyl-, monoethyl ester, (3R)- (9CI)

Base Information

• Chemical Name: Pentanedioic acid, 3-phenyl-, monoethyl ester, (3R)- (9CI)
• CAS No.: 140863-09-8
• Molecular Formula: C13H16 O4
• Molecular Weight: 236.268
• Mol file: 140863-09-8.mol

Synonyms:Pentanedioicacid, 3-phenyl-, monoethyl ester, (3R)- (9CI); Pentanedioic acid, 3-phenyl-,monoethyl ester, (R)-; (R)-3-Phenylglutaric acid monoethyl ester

Chemical Property of Pentanedioic acid, 3-phenyl-, monoethyl ester, (3R)- (9CI)

Chemical Property:

• PSA: 63.60000
• LogP: 2.19810

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pentanedioic acid, 3-phenyl-, monoethyl ester, (3R)- (9CI)

There total 5 articles about Pentanedioic acid, 3-phenyl-, monoethyl ester, (3R)- (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:

3-phenylglutaric acid anhydride (4160-80-9) + ethanol (64-17-5) → (R)-3-phenylglutaric acid monoethyl ester (140863-09-8) + (S)-3-phenylglutaric acid monoethyl ester (137654-26-3)

Guidance literature:

With lipase Chirazyme L-2; In various solvent(s); at 20 ℃; for 48h; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2005.04.032

Reference yield:

3-phenylglutaric acid (4165-96-2) → (R)-3-phenylglutaric acid monoethyl ester (140863-09-8)

Guidance literature:

Multi-step reaction with 2 steps

1: AcCl / 3 h

2: Amano PS-C immobilized / diisopropyl ether / 19 h / 20 °C

With Amano PS-C immobilized; acetyl chloride; In di-isopropyl ether;

DOI:10.1016/j.tetasy.2005.06.025

Reference yield:

benzaldehyde (100-52-7) → (R)-3-phenylglutaric acid monoethyl ester (140863-09-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: piperidine / 72 h / 20 °C

1.2: aq. KOH / 3 h / 80 - 95 °C

2.1: AcCl / 3 h

3.1: Amano PS-C immobilized / diisopropyl ether / 19 h / 20 °C

With piperidine; Amano PS-C immobilized; acetyl chloride; In di-isopropyl ether;

DOI:10.1016/j.tetasy.2005.06.025

upstream raw materials:

ketene diethyl acetal

(6S,7S,10R)-7-Isopropyl-5-(4-methoxy-phenyl)-10-methyl-3-[1-phenyl-meth-(Z)-ylidene]-1-oxa-5-aza-spiro[5.5]undecane-2,4-dione

(R)-3-(4-Methoxy-phenyl)-4,6-dioxo-2-phenyl-5-[1-phenyl-meth-(Z)-ylidene]-[1,3]oxazinane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

3-phenylglutaric acid anhydride

Refernces

• 1、 Fryszkowska, Anna,Komar, Marta,Koszelewski, Dominik,Ostaszewski, Ryszard. "Studies on enzymatic synthesis of chiral non-racemic 3-arylglutaric acid monoesters". . p. 961 - 966. Retrieved 2007/10/03.
• 2、 Fryszkowska, Anna,Komar, Marta,Koszelewski, Dominik,Ostaszewski, Ryszard. "Enzymatic desymmetrization of 3-arylglutaric acid anhydrides". . p. 2475 - 2485. Retrieved 2007/10/03.