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

Base Information

• Chemical Name: <(5S)-5-benzyloxycarbonylamino-5-benzyloxycarbonyl>-2-oxapentanoyl-S-acetyl-2-methoxy-(2R/S)-cysteinyl-(2R)-valine benzyl ester
• CAS No.: 126166-91-4
• Molecular Formula: C₃₈H₄₅N₃O₁₁S
• Molecular Weight: 751.855
• Mol file: 126166-91-4.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about <(5S)-5-benzyloxycarbonylamino-5-benzyloxycarbonyl>-2-oxapentanoyl-S-acetyl-2-methoxy-(2R/S)-cysteinyl-(2R)-valine 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: 66.0%

<(5S)-5-benzyloxycarbonylamino-5-benzyloxycarbonyl>-2-oxapentanoyl-3-bromo-2-methoxy-(2R/S)-alaninyl-(2R)-valine benzyl ester (126166-90-3,126252-90-2) + potassium thioacetate (10387-40-3) → <(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:

In N,N-dimethyl-formamide; at 35 - 40 ℃; for 5h;

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

Reference yield:

benzyl L-2-<(carbobenzxyloxy)amino>-4-hydroxybutyrate (58578-44-2) → <(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 6 steps

1: 96 percent / CH₂Cl₂ / 20 h / Ambient temperature

2: 80 percent / dimethylaminopyridine / acetonitrile / 45 deg C, 24 h, then RT, 36 h

3: mCPBA / CH₂Cl₂ / 0.75 h / Ambient temperature

4: xylene / 4 h / 150 °C

5: 83 percent / Br₂ / CH₂Cl₂ / 0.33 h / -10 °C

6: 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

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:

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

potassium thioacetate

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

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