N-benzyloxycarbonyl-O-carbonylimidazole-(2S)-homoserine benzyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-O-carbonylimidazole-(2S)-homoserine benzyl ester
• CAS No.: 126166-87-8
• Molecular Formula: C₂₃H₂₃N₃O₆
• Molecular Weight: 437.452
• Mol file: 126166-87-8.mol

Synonyms:N-benzyloxycarbonyl-O-carbonylimidazole-(2S)-homoserine benzyl ester

Chemical Property of N-benzyloxycarbonyl-O-carbonylimidazole-(2S)-homoserine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl-O-carbonylimidazole-(2S)-homoserine benzyl ester

There total 1 articles about N-benzyloxycarbonyl-O-carbonylimidazole-(2S)-homoserine benzyl 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: 96.0%

benzyl L-2-<(carbobenzxyloxy)amino>-4-hydroxybutyrate (58578-44-2) + 1,1'-carbonyldiimidazole (530-62-1) → N-benzyloxycarbonyl-O-carbonylimidazole-(2S)-homoserine benzyl ester (126166-87-8)

Guidance literature:

In dichloromethane; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(01)80113-7

Reference yield: 80.0%

S-benzyl-(2R)-cysteinyl-(2R)-valine benzyl ester (82259-16-3) + N-benzyloxycarbonyl-O-carbonylimidazole-(2S)-homoserine benzyl ester (126166-87-8) → <(5S)-5-benzyloxycarbonylamino-5-benzyloxycarbonyl>-2-oxapentanoyl-S-benzyl-(2R)-cysteinyl-(2R)-valine benzyl ester (126166-88-9)

Guidance literature:

With dmap; In acetonitrile; 45 deg C, 24 h, then RT, 36 h;

DOI:10.1016/S0040-4020(01)80113-7

Reference yield:

N-benzyloxycarbonyl-O-carbonylimidazole-(2S)-homoserine benzyl ester (126166-87-8) → <(5S)-5-benzyloxycarbonylamino-5-benzyloxycarbonyl>-2-oxapentanoyl-S-acetyl-2-methoxy-(2R/S)-cysteinyl-(2R)-valine benzyl ester (126166-91-4,126252-91-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / dimethylaminopyridine / acetonitrile / 45 deg C, 24 h, then RT, 36 h

2: mCPBA / CH₂Cl₂ / 0.75 h / Ambient temperature

3: xylene / 4 h / 150 °C

4: 83 percent / Br₂ / CH₂Cl₂ / 0.33 h / -10 °C

5: 66 percent / dimethylformamide / 5 h / 35 - 40 °C

With dmap; bromine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; xylene;

DOI:10.1016/S0040-4020(01)80113-7

upstream raw materials:

benzyl L-2-<(carbobenzxyloxy)amino>-4-hydroxybutyrate

1,1'-carbonyldiimidazole

Downstream raw materials:

<(5S)-5-benzyloxycarbonylamino-5-benzyloxycarbonyl>-2-oxapentanoyl-S-benzyl-(2R)-cysteinyl-(2R)-valine benzyl ester

<(5S)-5-benzyloxycarbonylamino-5-benzyloxycarbonyl>-2-oxapentanoyldidehydroalaninyl-(2R)-valine benzyl ester

<(5S)-5-benzyloxycarbonylamino-5-benzyloxycarbonyl>-2-oxapentanoyl-3-bromo-2-methoxy-(2R/S)-alaninyl-(2R)-valine benzyl ester

<(5S)-5-benzyloxycarbonylamino-5-benzyloxycarbonyl>-2-oxapentanoyl-S-acetyl-2-methoxy-(2R/S)-cysteinyl-(2R)-valine benzyl ester