(2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide

Base Information

• Chemical Name: (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide
• CAS No.: 141171-72-4
• Molecular Formula: C₂₇H₃₅N₃O₅
• Molecular Weight: 481.592
• Mol file: 141171-72-4.mol

Synonyms:(2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide

Chemical Property of (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide

There total 10 articles about (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl 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: 72.0%

(2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-59-0,76498-22-1) + (S)-Pyrrolidine-2-carboxylic acid tert-butylamide; compound with trifluoro-acetic acid → (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide (141171-72-4)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 18h;

DOI:10.1021/ja00153a008

Reference yield: 23.0%

(3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid (222848-56-8,76498-22-1) + L-proline tert-butylamide (128018-18-8) → 1-<(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide (191849-91-9) + (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide (141171-72-4)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; a) 0 deg C, 1 h, b) RT, 2.5 h;

DOI:10.1248/cpb.42.2636

Reference yield:

(2R,3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid (62023-60-3,76498-22-1) + (2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid (62023-59-0,76498-22-1) + L-proline tert-butylamide (128018-18-8) → 1-<(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide (191849-91-9) + (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide (141171-72-4)

Guidance literature:

(2R,3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid; (2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid; With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

L-proline tert-butylamide; In DMF (N,N-dimethyl-formamide); for 18h;

upstream raw materials:

(3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid

L-proline tert-butylamide

(2S,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid

Z-Pro-NH^tBu

Downstream raw materials:

((S)-1-{(S)-1-[(1S,2S)-1-Benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-2-carbamoyl-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester

((R)-1-{(S)-1-[(1S,2S)-1-Benzyl-3-((S)-2-tert-butylcarbamoyl-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propylcarbamoyl]-2-carbamoyl-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid benzyl ester

Refernces

• 1、 Asagarasu, Akira,Uchiyama, Taketo,Achiwa, Kazuo. "Syntheses of HIV-protease inhibitors having a peptide moiety which binds to GP120". . p. 697 - 703. Retrieved 2007/10/03.
• 2、 Slee,Slee, Deborah H.,Laslo,Laslo, Karen L.,Elder,Elder, John H.,Ollmann,Ollmann, Ian R.,Gustchina,Gustchina, Alla,Kervinen,Kervinen, Jukka,Zdanov,Zdanov, Alexander,Wlodawer,Wlodawer, Alexander,Wong,Wong, Chi-Huey. "Selectivity in the inhibition of HIV and FIV protease: Inhibitory and mechanistic studies of pyrrolidine-containing α-keto amide and hydroxyethylamine core structures". . p. 11867 - 11878. Retrieved 2007/10/03.