(-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU

Base Information

• Chemical Name: (-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU
• CAS No.: 244277-48-3
• Molecular Formula: C12H14 O4
• Molecular Weight: 222.241
• Mol file: 244277-48-3.mol

Synonyms:(-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU;(-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBUTYRATE, CIBA CS PROD

Chemical Property of (-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU

Chemical Property:

• Melting Point: 35-38 °C
• PSA: 63.60000
• LogP: 1.18340
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU

There total 12 articles about (-)-ETHYL (R)-2-HYDROXY-4-OXO-4-PHENYLBU 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: 92.0%

(R)-(-)-2-hydroxy-4-phenyl-pent-4-enoic acid ethyl ester (208242-81-3) → ethyl (R)-(-)-2-hydroxy-4-oxo-4-phenylbutanoate (244277-48-3)

Guidance literature:

(R)-(-)-2-hydroxy-4-phenyl-pent-4-enoic acid ethyl ester; With ozone; In methanol; at -78 ℃; for 0.5h;

With triphenylphosphine; In methanol; at -78 - 20 ℃; Further stages.;

DOI:10.1021/ol071342d

Reference yield: 80.0%

ethyl 2,4-dioxo-4-phenylbutyrate (6296-54-4) → ethyl (R)-(-)-2-hydroxy-4-oxo-4-phenylbutanoate (244277-48-3)

Guidance literature:

With D-glucose; 1-chloroacetophenone; In diethyl ether; at 28 ℃; optical yield given as %ee; aq. buffer; Enzymatic reaction;

DOI:10.1021/jo902227f

Reference yield: 80.0%

ethyl 2,4-dioxo-4-phenylbutyrate (6296-54-4) → 3-hydroxy-1-phenylpropan-1-one (5650-41-9) + (R)-2-hydroxy-4-oxo-4-phenylbutanoic acid (146912-66-5) + ethyl (R)-(-)-2-hydroxy-4-oxo-4-phenylbutanoate (244277-48-3)

Guidance literature:

With Saccharomyces cerevisiae cells; 1-chloroacetophenone; In di-isopropyl ether; water; at 20 ℃; for 48h; pH=4.5;

DOI:10.1016/j.tetasy.2004.09.007

upstream raw materials:

1-styrenyloxytrimethylsilane

N-benzoylhydroxyglycine ethyl ester

ethyl 2,4-dioxo-4-phenylbutyrate

ethyl-(Z)-2-hydroxy-4-oxo-4-phenyl-but-2-enoate

Downstream raw materials:

ethyl (R)-(-)-2-hydroxy-3-methylene-4-oxophenylbutanoate

(-)-ethyl (R)-2-hydroxy-4-cyclohexylbutyrate

(+)-ethyl (S)-2-N-benzylamino-4-phenylbutyrate

(R)-2-<(4-nitrobenzolsulfonyl)oxy>-4-phenylbuttersaeure-ethylester

Refernces

• 1、 Mo, Yuan-Zhao,Nie, Hui-Fang,Lei, Yang,Zhang, Dong-Xu,Li, Xiao-Ye,Zhang, Sheng-Yong,Wang, Qiao-Feng. "Asymmetric transfer hydrogenation of γ-aryl α,γ-dioxo-butyric acid esters". . p. 33126 - 33131. Retrieved 2016/05/09.
• 2、 Milagre, Cintia D. F.,Milagre, Humberto M. S.,Moran, Paula J. S.,Rodrigues, J. Augusto R.. "Chemoenzymatic synthesis of α-Hydroxy-β-methyl-γ-hydroxy esters: Role of the keto-enol equilibrium to control the stereoselective hydrogenation in a key step". experimental part. p. 1410 - 1418. Retrieved 2010/05/19.