(S)-3-HYDROXYGLUTARATE ETHYL

Base Information

• Chemical Name: (S)-3-HYDROXYGLUTARATE ETHYL
• CAS No.: 95310-88-6
• Molecular Formula: C7H12 O5
• Molecular Weight: 176.17
• Hs Code.: 2918990090
• Mol file: 95310-88-6.mol

Synonyms:Pentanedioicacid, 3-hydroxy-, monoethyl ester, (R)-

Chemical Property of (S)-3-HYDROXYGLUTARATE ETHYL

Chemical Property:

• PSA: 83.83000
• LogP: -0.22480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-3-HYDROXYGLUTARATE ETHYL

There total 5 articles about (S)-3-HYDROXYGLUTARATE ETHYL 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: 95.0%

(R)-ethyl 4-cyano-3-hydroxybutyrate (141942-85-0) → (3R)-5-ethoxy-3-hydroxy-5-oxopentanoic acid (95310-88-6)

Guidance literature:

With recombinant nitrilase from Arabidopsis thaliana; In aq. buffer; at 25 ℃; for 4.5h; pH=8; pH-value; Temperature; Reagent/catalyst; Concentration; Enzymatic reaction;

DOI:10.1002/cctc.201402877

Reference yield: 70.0%

diethyl 3-hydroxyglutarate (32328-03-3) → (3R)-5-ethoxy-3-hydroxy-5-oxopentanoic acid (95310-88-6)

Guidance literature:

With Acinetobacter lowfii; In various solvent(s); for 48h; Product distribution; Microrganism: Soil isolate S-29. Object: enantioselective hydrolysis.;

DOI:10.1016/S0040-4039(01)81572-0

Reference yield:

diethyl 3-hydroxyglutarate (32328-03-3) → (3S)-5-ethoxy-3-hydroxy-5-oxopentanoic acid (95310-87-5) + (3R)-5-ethoxy-3-hydroxy-5-oxopentanoic acid (95310-88-6)

Guidance literature:

With Candida antarctica lipase B; water; sodium hydroxide; at 70 ℃; pH=7; aq. phosphate buffer;

DOI:10.1016/j.molcatb.2010.03.009

upstream raw materials:

diethyl 3-hydroxyglutarate

(R)-ethyl 4-cyano-3-hydroxybutyrate

ethyl 3-acetoxypentanedioate

(3R)-3-(acetyloxy)-5-ethoxy-5-oxopentanoic acid

Downstream raw materials:

(3R)-3-(acetyloxy)-5-ethoxy-5-oxopentanoic acid

ethyl (3R)-(tert-butyldimethylsilyloxy)-5-oxo-6-(triphenylphosphoranylidene)-hexanoate

Refernces

• 1、 Metzner, Richard,Hummel, Werner,Wetterich, Frank,K?nig, Burghard,Gr?ger, Harald. "Integrated Biocatalysis in Multistep Drug Synthesis without Intermediate Isolation: A de Novo Approach toward a Rosuvastatin Key Building Block". . p. 635 - 638. Retrieved 2015/06/30.
• 2、 Dong, Hua-Ping,Wang, Ya-Jun,Zheng, Yu-Guo. "Enantioselective hydrolysis of diethyl 3-hydroxyglutarate to ethyl (S)-3-hydroxyglutarate by immobilized Candida antarctica lipase B". scheme or table. p. 90 - 94. Retrieved 2011/01/03.