(4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester

Base Information

• Chemical Name: (4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester
• CAS No.: 112271-08-6
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4
• Mol file: 112271-08-6.mol

Synonyms:(4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester

Chemical Property of (4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester

Chemical Property:

• Melting Point: 67.0-68.0 °C
• Boiling Point: 456.7±40.0 °C(Predicted)
• Density: 1.115±0.06 g/cm3(Predicted)

Purity/Quality:

99%+, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester

There total 17 articles about (4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester 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%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + ethyl potassium malonate (6148-64-7) → (4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester (112271-08-6)

Guidance literature:

With 1,1'-carbonyldiimidazole; magnesium chloride;

DOI:10.1016/j.tetlet.2005.08.138

Reference yield: 85.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + ethyl acetate (141-78-6) → (4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester (112271-08-6)

Guidance literature:

N-tert-butoxycarbonyl-L-phenylalanine; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 ℃; for 24h;

ethyl acetate; In tetrahydrofuran; at -78 ℃; for 1h; Further stages.;

DOI:10.1021/ol006779z

Reference yield: 80.0%

diazoacetic acid ethyl ester (623-73-4) + Boc-L-phenylalaninal (72155-45-4) → (4S)-40<(tertibutyloxycarbonyl)amino>-3-oxo-5-phenylpentanoic acid ethyl ester (112271-08-6)

Guidance literature:

With tin(ll) chloride; In dichloromethane;

DOI:10.1021/ol403290h

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

magnesium bis(3-ethoxy-3-oxopropanoate)

Dibasic magnesium salt of ethyl hydrogen malonate

Boc-4-amino-3-hydroxy-5-phenylpentanoic acid ethyl ester

Downstream raw materials:

(1'R,2'R)-N-<2,4-dihydroxy-4-oxo-1-(phenylmethyl)butyl>carbamic acid 1,1-dimethylethyl ester

C₃₃H₄₈N₄O₇

C₂₃H₃₂N₄O₃

(S)-tert-butyl 1-(7-methoxy-2-oxo-2H-chromen-4-yl)-2-phenylethylcarbamate

Refernces

• 1、 Nishi, T.,Kitamura, M.,Ohkuma, T.,Noyori, R.. "SYNTHESIS OF ASATINE AND ITS ANALOGUES BY HOMOGENEOUS ASYMMETRIC HYDROGENATION". . p. 6327 - 6330. Retrieved 1988.
• 2、 Winiecka, Iwona,Jaworski, Pawe?,Mazurek, Aleksander Pawe?,Marsza?ek, Dorota,Goldnik, Anna,Sokulski, Daniel. "Novel renin inhibitors containing derivatives of N-alkylleucyl-β-hydroxy-γ-amino acids". . p. 106 - 115. Retrieved 2016/02/09.
• 3、 Bandyopadhyay, Anupam,Malik, Ankita,Kumar, Mothukuri Ganesh,Gopi, Hosahudya N.. "Exploring β-hydroxy γ-amino acids (statines) in the design of hybrid peptide foldamers". . p. 294 - 297. Retrieved 2014/01/23.