ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate

Base Information

• Chemical Name: ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate
• CAS No.: 158744-36-6
• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.417
• Mol file: 158744-36-6.mol

Synonyms:ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate

Chemical Property of ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate

There total 6 articles about ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate 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: 89.0%

N-carbobenzoxy-L-phenylalanine methyl ester (35909-92-3) + ethyl acetate (141-78-6) → ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate (158744-36-6)

Guidance literature:

ethyl acetate; With lithium diisopropyl amide; In tetrahydrofuran; n-heptane; ethylbenzene; at -50 ℃;

N-carbobenzoxy-L-phenylalanine methyl ester; In tetrahydrofuran; n-heptane; ethylbenzene; at -50 ℃;

DOI:10.1016/S0040-4039(03)00464-7

Reference yield: 64.0%

ethyl bromoacetate (105-36-2) + (S)-1-(2'-benzyloxycarbonylamino-3'-phenylpropanoyl)-3,5-dimethylpyrazole (62023-57-8) → ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate (158744-36-6)

Guidance literature:

With zinc; In tetrahydrofuran; for 1h; Heating;

Reference yield:

N-Cbz-L-Phe (1161-13-3) → ethyl (S)-4-benzyloxycarbonylamino-3-oxo-5-phenylpentanoate (158744-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / Et₃N, SOCl₂ / benzene / 3 h / 5 °C

2: 64 percent / Zn / tetrahydrofuran / 1 h / Heating

With thionyl chloride; triethylamine; zinc; In tetrahydrofuran; benzene;

upstream raw materials:

N-Cbz-L-Phe

Dibasic magnesium salt of ethyl hydrogen malonate

ethyl bromoacetate

(S)-1-(2'-benzyloxycarbonylamino-3'-phenylpropanoyl)-3,5-dimethylpyrazole

Downstream raw materials:

Ethyl 4(S)-(benzyloxyformamido)-3(R)-hydroxy-5-phenylpentanoate

Ethyl 4(S)-(benzyloxyformamido)-3(S)-hydroxy-5-phenylpentanoate

(S)-5-Benzyloxycarbonylamino-4-oxo-6-phenyl-hexanoic acid ethyl ester

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