(S)-4-[N-(benzyloxycarbonyl)-L-alanyl-L-valyl-L-leucyl]amino-6,6,6-trifluoro-5-oxohexanoic acid

Base Information

• Chemical Name: (S)-4-[N-(benzyloxycarbonyl)-L-alanyl-L-valyl-L-leucyl]amino-6,6,6-trifluoro-5-oxohexanoic acid
• CAS No.: 911034-11-2
• Molecular Formula: C₂₈H₃₉F₃N₄O₈
• Molecular Weight: 616.635
• Mol file: 911034-11-2.mol

Synonyms:

Chemical Property of (S)-4-[N-(benzyloxycarbonyl)-L-alanyl-L-valyl-L-leucyl]amino-6,6,6-trifluoro-5-oxohexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[N-(benzyloxycarbonyl)-L-alanyl-L-valyl-L-leucyl]amino-6,6,6-trifluoro-5-oxohexanoic acid

There total 12 articles about (S)-4-[N-(benzyloxycarbonyl)-L-alanyl-L-valyl-L-leucyl]amino-6,6,6-trifluoro-5-oxohexanoic acid 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:

(4S,5S)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-(trimethylsilyloxy)oxazolidine-3-carboxylate (911033-98-2) → (S)-4-[N-(benzyloxycarbonyl)-L-alanyl-L-valyl-L-leucyl]amino-6,6,6-trifluoro-5-oxohexanoic acid (911034-11-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / NaBH₄ / methanol / 16 h / 20 °C

2: 100 percent / H₂ / Pd/C / methanol / 16 h / 20 °C

3: HOBt; EDC*HCl / dimethylformamide / 0 - 20 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

5: TFA / CH₂Cl₂ / 0 - 20 °C

With sodium tetrahydroborate; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.06.052

Reference yield:

N-benzyloxycarbonyl-L-glutamic acid (1155-62-0) → (S)-4-[N-(benzyloxycarbonyl)-L-alanyl-L-valyl-L-leucyl]amino-6,6,6-trifluoro-5-oxohexanoic acid (911034-11-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 100 percent / p-TsOH*H₂O / toluene / 1.67 h / Heating

2: 45 percent / DMAP; ECD*HCl; Et₃N / tetrahydrofuran / 16 h / 20 °C

3: 92 percent / cesium fluoride / tetrahydrofuran / 2 h / 20 °C / sonication

4: 68 percent / NaBH₄ / methanol / 16 h / 20 °C

5: 100 percent / H₂ / Pd/C / methanol / 16 h / 20 °C

6: HOBt; EDC*HCl / dimethylformamide / 0 - 20 °C

7: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

8: TFA / CH₂Cl₂ / 0 - 20 °C

With dmap; sodium tetrahydroborate; ECD*HCl; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; cesium fluoride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2006.06.052

Reference yield:

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid (23632-67-9) → (S)-4-[N-(benzyloxycarbonyl)-L-alanyl-L-valyl-L-leucyl]amino-6,6,6-trifluoro-5-oxohexanoic acid (911034-11-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 45 percent / DMAP; ECD*HCl; Et₃N / tetrahydrofuran / 16 h / 20 °C

2: 92 percent / cesium fluoride / tetrahydrofuran / 2 h / 20 °C / sonication

3: 68 percent / NaBH₄ / methanol / 16 h / 20 °C

4: 100 percent / H₂ / Pd/C / methanol / 16 h / 20 °C

5: HOBt; EDC*HCl / dimethylformamide / 0 - 20 °C

6: Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

7: TFA / CH₂Cl₂ / 0 - 20 °C

With dmap; sodium tetrahydroborate; ECD*HCl; hydrogen; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; cesium fluoride; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.06.052

upstream raw materials:

(4S)-tert-butyl 4-amino-6,6,6-trifluoro-5-hydroxyhexanoate

(4S)-tert-butyl 4-(benzyloxycarbonyl)amino-6,6,6-trifluoro-5-hydroxyhexanoate

(4S,5R)-benzyl 4-[2-(tert-butoxycarbonyl)ethyl]-5-trifluoromethyl-5-hydroxyoxazolidine-3-carboxylate

N-benzyloxycarbonyl-L-alanyl-L-valyl-L-leucine