L-Phenylalaninamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-(hydroxymethyl)ethyl]-

Base Information

• Chemical Name: L-Phenylalaninamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-(hydroxymethyl)ethyl]-
• CAS No.: 199005-70-4
• Molecular Formula: C₃₁H₄₄N₄O₇
• Molecular Weight: 584.713
• DSSTox Substance ID: DTXSID501102688
• Mol file: 199005-70-4.mol

Synonyms:DTXSID501102688;199005-70-4;L-Phenylalaninamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-(hydroxymethyl)ethyl]-

Chemical Property of L-Phenylalaninamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-(hydroxymethyl)ethyl]-

Chemical Property:

• XLogP3: 3.9
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 17
• Exact Mass: 584.32099976
• Heavy Atom Count: 42
• Complexity: 849

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)CC(C(=O)NC(CC1=CC=CC=C1)C(=O)NC(CNC(=O)OC(C)(C)C)CO)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)N[C@@H](CNC(=O)OC(C)(C)C)CO)NC(=O)OCC2=CC=CC=C2

Technology Process of L-Phenylalaninamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-(hydroxymethyl)ethyl]-

There total 5 articles about L-Phenylalaninamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-2-[[(1,1-dimethylethoxy)carbonyl]amino]-1-(hydroxymethyl)ethyl]- 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:

di-tert-butyl dicarbonate (24424-99-5) → {(S)-1-[(S)-1-((S)-2-tert-Butoxycarbonylamino-1-hydroxymethyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester (199005-70-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / aq. NaOH / 2-methyl-propan-2-ol / 12 h / Ambient temperature

2: 100 percent / diethyl ether; ethanol / 0.5 h / 0 °C

3: 96 percent / LiCl, NaBH₄ / tetrahydrofuran; ethanol / Ambient temperature

4: 98 percent / H₂ / 10percent Pd/C / methanol / 2 h

5: dimethylformamide; CH₂Cl₂ / Ambient temperature

With sodium hydroxide; sodium tetrahydroborate; hydrogen; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jm980071x

Reference yield:

N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine (16947-84-5,62234-36-0) → {(S)-1-[(S)-1-((S)-2-tert-Butoxycarbonylamino-1-hydroxymethyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester (199005-70-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / diethyl ether; ethanol / 0.5 h / 0 °C

2: 96 percent / LiCl, NaBH₄ / tetrahydrofuran; ethanol / Ambient temperature

3: 98 percent / H₂ / 10percent Pd/C / methanol / 2 h

4: dimethylformamide; CH₂Cl₂ / Ambient temperature

With sodium tetrahydroborate; hydrogen; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm980071x

Reference yield:

methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate (58457-98-0) → {(S)-1-[(S)-1-((S)-2-tert-Butoxycarbonylamino-1-hydroxymethyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester (199005-70-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / LiCl, NaBH₄ / tetrahydrofuran; ethanol / Ambient temperature

2: 98 percent / H₂ / 10percent Pd/C / methanol / 2 h

3: dimethylformamide; CH₂Cl₂ / Ambient temperature

With sodium tetrahydroborate; hydrogen; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm980071x

upstream raw materials:

di-tert-butyl dicarbonate

N-benzyloxycarbonyl-L-leucyl-L-phenylalanine

N-[(benzyloxy)carbonyl]-3-[(tert-butoxycarbonyl)amino]-L-alanine

methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-[(tert-butoxycarbonyl)amino]propanoate

Downstream raw materials:

{(S)-1-[(S)-1-((S)-2-tert-Butoxycarbonylamino-1-formyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester