(5S,6S)-3-aza-3-benzyl-6-{[(tert-butyloxycarbonyl)-L-valinyl]amino}-5-hydroxy-7-phenylheptanoyl amide

Base Information

• Chemical Name: (5S,6S)-3-aza-3-benzyl-6-{[(tert-butyloxycarbonyl)-L-valinyl]amino}-5-hydroxy-7-phenylheptanoyl amide
• CAS No.: 866227-36-3
• Molecular Formula: C₂₉H₄₂N₄O₅
• Molecular Weight: 526.676
• Mol file: 866227-36-3.mol

Synonyms:

Chemical Property of (5S,6S)-3-aza-3-benzyl-6-{[(tert-butyloxycarbonyl)-L-valinyl]amino}-5-hydroxy-7-phenylheptanoyl amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S)-3-aza-3-benzyl-6-{[(tert-butyloxycarbonyl)-L-valinyl]amino}-5-hydroxy-7-phenylheptanoyl amide

There total 4 articles about (5S,6S)-3-aza-3-benzyl-6-{[(tert-butyloxycarbonyl)-L-valinyl]amino}-5-hydroxy-7-phenylheptanoyl amide 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:

2-[((2S,3S)-3-Amino-2-hydroxy-4-phenyl-butyl)-benzyl-amino]-acetamide + t-Boc-L-valine (13734-41-3) → (5S,6S)-3-aza-3-benzyl-6-{[(tert-butyloxycarbonyl)-L-valinyl]amino}-5-hydroxy-7-phenylheptanoyl amide (866227-36-3)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmc.2005.06.048

Reference yield:

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane (98760-08-8) → (5S,6S)-3-aza-3-benzyl-6-{[(tert-butyloxycarbonyl)-L-valinyl]amino}-5-hydroxy-7-phenylheptanoyl amide (866227-36-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 82 percent / propan-2-ol / 50 °C

2.1: K₂CO₃ / dimethylformamide / 20 °C

2.2: 70 percent / ammonia / methanol / 20 °C

3.1: CF₃CO₂H / CH₂Cl₂ / 0.25 h / 20 °C

4.1: 0.19 g / N,N-diisopropylethylamine; O-(benzotriazol-1-yl)-N,N,N'N'-tetramethyluronium BF₄ / dimethylformamide / 20 °C

With potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/j.bmc.2005.06.048

Reference yield:

benzylamine (100-46-9) → (5S,6S)-3-aza-3-benzyl-6-{[(tert-butyloxycarbonyl)-L-valinyl]amino}-5-hydroxy-7-phenylheptanoyl amide (866227-36-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 82 percent / propan-2-ol / 50 °C

2.1: K₂CO₃ / dimethylformamide / 20 °C

2.2: 70 percent / ammonia / methanol / 20 °C

3.1: CF₃CO₂H / CH₂Cl₂ / 0.25 h / 20 °C

4.1: 0.19 g / N,N-diisopropylethylamine; O-(benzotriazol-1-yl)-N,N,N'N'-tetramethyluronium BF₄ / dimethylformamide / 20 °C

With potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/j.bmc.2005.06.048

upstream raw materials:

t-Boc-L-valine

(2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane

benzylamine

(2S,3S)-1-(benzylamino)-3-[N-(tert-butyloxycarbonyl)amino]-4-phenylbutan-2-ol