{(S)-1-[3-({(1S,2S)-3-[(S)-1-(3-Aminomethyl-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-methyl)-oxiranyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(S)-1-[3-({(1S,2S)-3-[(S)-1-(3-Aminomethyl-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-methyl)-oxiranyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
• CAS No.: 118404-94-7
• Molecular Formula: C₄₂H₆₃N₅O₇
• Molecular Weight: 749.992
• Mol file: 118404-94-7.mol

Synonyms:

Chemical Property of {(S)-1-[3-({(1S,2S)-3-[(S)-1-(3-Aminomethyl-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-methyl)-oxiranyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(S)-1-[3-({(1S,2S)-3-[(S)-1-(3-Aminomethyl-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-methyl)-oxiranyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

There total 4 articles about {(S)-1-[3-({(1S,2S)-3-[(S)-1-(3-Aminomethyl-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-methyl)-oxiranyl]-2-phenyl-ethyl}-carbamic acid tert-butyl 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:

((E)-(S)-4-{(1S,2S)-3-[(S)-1-(3-Aminomethyl-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-1-benzyl-but-2-enyl)-carbamic acid tert-butyl ester → {(S)-1-[3-({(1S,2S)-3-[(S)-1-(3-Aminomethyl-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-methyl)-oxiranyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (118404-94-7,124338-90-5,124339-21-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 72h; Ambient temperature;

DOI:10.1021/jm00164a058

Reference yield:

Boc-L-phenylalaninal (72155-45-4) → {(S)-1-[3-({(1S,2S)-3-[(S)-1-(3-Aminomethyl-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-methyl)-oxiranyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (118404-94-7,124338-90-5,124339-21-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, hexane, -80 deg C, 1 h, 2.) a) -80 deg C, 1 h, b) room temp.

2: 1.) (cyclohexyl)2BH, 2.) 2 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 1 h, 2.) MeOH, room temp., 1 h

3: HOBT/DCC, Et₃N / dimethylformamide / 1.) 0 deg C, 0.5 h, 2.) room temp.

4: m-chloroperbenzoic acid / CH₂Cl₂ / 72 h / Ambient temperature

With sodium hydroxide; n-butyllithium; bis(cyclohexanyl)borane; dihydrogen peroxide; benzotriazol-1-ol; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00164a058

Reference yield:

(S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid (82042-48-6) → {(S)-1-[3-({(1S,2S)-3-[(S)-1-(3-Aminomethyl-benzylcarbamoyl)-3-methyl-butylcarbamoyl]-1-cyclohexylmethyl-2-hydroxy-propylcarbamoyl}-methyl)-oxiranyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (118404-94-7,124338-90-5,124339-21-5)

Guidance literature:

Multi-step reaction with 2 steps

1: HOBT/DCC, Et₃N / dimethylformamide / 1.) 0 deg C, 0.5 h, 2.) room temp.

2: m-chloroperbenzoic acid / CH₂Cl₂ / 72 h / Ambient temperature

With benzotriazol-1-ol; triethylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00164a058

upstream raw materials:

Boc-L-phenylalaninal

(S)-5-<(tert-Butoxycarbonyl)amino>-6-phenyl-(E)-3-hexenoic acid

(E)-(S)-<1-(phenylmethyl)-5-(trimethylsilyl)-3-hexen-5-ynyl>carbamic acid 1,1-dimethylethyl ester