(2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester

Base Information

• Chemical Name: (2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester
• CAS No.: 288068-80-4
• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.407
• Mol file: 288068-80-4.mol

Synonyms:(2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester

Chemical Property of (2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester

There total 5 articles about (2S)-2-benzyloxycarbonylamino-4-phenylbutyric 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: 99.0%

benzyl chloroformate (501-53-1,94274-21-2) + L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride (90891-21-7) → (2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester (288068-80-4)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1016/S0957-4166(03)00408-7

Reference yield: 74.0%

ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate (134746-23-9) + phenethylzinc iodide → (2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester (288068-80-4)

Guidance literature:

With nickel(II) bromide dimethoxyethane; 2,6-bis((4R,5S)-4-isopropyl-5-phenyl-4,5-dihydrooxazol-2-yl)pyridine; In tetrahydrofuran; at 0 ℃; for 4h; enantioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.1c03903

Reference yield:

(Z)-2-Benzyloxycarbonylamino-4-phenyl-but-2-enoic acid ethyl ester → (2S)-2-benzyloxycarbonylamino-4-phenylbutyric acid ethyl ester (288068-80-4)

Guidance literature:

With (R)-N-diphenylphosphino-N-methyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine; hydrogen; bis(cycloocta-1,5-diene)rhodium(I) trifluoromethanesulfonate; In tetrahydrofuran; at 25 ℃; for 6h; under 517.148 Torr;

DOI:10.1021/jo048312y

upstream raw materials:

benzyl chloroformate

L-(+)-α-amino-4-phenylbutyric acid ethyl ester hydrochloride

2-phenethyl iodide

ethyl 2-(((benzyloxy)carbonyl)amino)-2-chloroacetate

Downstream raw materials:

Z-homophenylalanine

(1S)-(1-methoxycarbamoyl-3-phenylpropyl)carbamic acid benzyl ester

(S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-hydroxy-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester

(S)-2-{(R)-2-[3-((S)-2-Benzyloxycarbonylamino-4-phenyl-butyrylamino)-2-oxo-pentanoylamino]-4-methyl-pentanoylamino}-3-methyl-butyric acid tert-butyl ester