L-Phenylalaninamide, N-[(2R,4S,5S)-5-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[[(1,1-dimethyl ethyl)dimethylsilyl]oxy]-1-oxo-6-phenyl-2-(phenylmethyl)hexyl]-L-leucyl-

Base Information

• Chemical Name: L-Phenylalaninamide, N-[(2R,4S,5S)-5-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[[(1,1-dimethyl ethyl)dimethylsilyl]oxy]-1-oxo-6-phenyl-2-(phenylmethyl)hexyl]-L-leucyl-
• CAS No.: 126410-32-0
• Molecular Formula: C45H66N4O6Si
• Molecular Weight: 787.128
• Mol file: 126410-32-0.mol

Synonyms:

Chemical Property of L-Phenylalaninamide, N-[(2R,4S,5S)-5-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[[(1,1-dimethyl ethyl)dimethylsilyl]oxy]-1-oxo-6-phenyl-2-(phenylmethyl)hexyl]-L-leucyl-

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Phenylalaninamide, N-[(2R,4S,5S)-5-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[[(1,1-dimethyl ethyl)dimethylsilyl]oxy]-1-oxo-6-phenyl-2-(phenylmethyl)hexyl]-L-leucyl-

There total 27 articles about L-Phenylalaninamide, N-[(2R,4S,5S)-5-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[[(1,1-dimethyl ethyl)dimethylsilyl]oxy]-1-oxo-6-phenyl-2-(phenylmethyl)hexyl]-L-leucyl- 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: 91.0%

leucylphenylalanylamide (38678-60-3) + N-(1,1-dimethylethoxycarbonyl)-5(S)-amino-4(S)-(t-butyldimethylsilyloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoic acid (98818-51-0) → {(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester (126410-32-0)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 15h;

DOI:10.1055/s-2003-37649

Reference yield:

α-bromo-p-toluidine (63516-03-0) → {(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester (126410-32-0)

Guidance literature:

Multi-step reaction with 6 steps

1: NaOEt / ethanol / 18 h / Ambient temperature

2: aq. LiOH / ethanol / 5 h

3: toluene / 24 h / Heating

4: aq. LiOH / 1,2-dimethoxy-ethane / 3 h / Ambient temperature

5: 1.) imidazole / 1.) DMF, RT, 24 h, 2.) DMF, MeOH, RT, 4 h

6: EDC*HCl, HOBt, Et₃N / dimethylformamide / 24 h / Ambient temperature

With 1H-imidazole; lithium hydroxide; sodium ethanolate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,2-dimethoxyethane; ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00088a004

Reference yield:

5(S)-(Boc-amino)-4(S)-hydroxy-6-phenyl-2(R)-phenylmethylhexanoic acid (98818-45-2) → {(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester (126410-32-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: imidazole / dimethylformamide / 24 h

1.2: 1.19 g / dimethylformamide; methanol / 3 h

2.1: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride; 1-hydroxybenzotriazole; Et₃N / dimethylformamide / 15 h / 20 °C

With 1H-imidazole; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1055/s-2003-37649

upstream raw materials:

leucylphenylalanylamide

N-(1,1-dimethylethoxycarbonyl)-5(S)-amino-4(S)-(t-butyldimethylsilyloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoic acid

N-tert-butoxycarbonyl-L-leucine

L-Phenylalanine amide

Downstream raw materials:

(5S)-(tert-butoxycarbonylamino)-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl-L-leucy-L-phenylalaninamide

(1S,4R)-{1-benzyl-4-[1-(1S)-carbamoyl-(2-phenylethylcarbamoyl)-(1S)-3-methylbutylcarbamoyl]-2-oxo-5-phenylpentyl}carbamic acid tert-butyl ester

L-364,505

((S)-1-{(1S,2S,4R)-1-Benzyl-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-2-hydroxy-5-phenyl-pentylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester

Refernces

• 1、 Dias, Luiz C.,Ferreira, Andrea A.,Diaz, Gaspar. "Short total synthesis of aspartyl protease inhibitors L-685,434, L-682,679 and L-685,458". . p. 1845 - 1849. Retrieved 2007/10/03.
• 2、 DeSolms,Giuliani,Guare,Vacca,Sanders,Graham,Wiggins,Darke,Sigal,Zugay,Emini,Schleif,Quintero,Anderson,Huff. "Design and synthesis of HIV protease inhibitors. Variations of the carboxy terminus of the HIV protease inhibitor L-682,679". . p. 2852 - 2857. Retrieved 2007/10/02.