(2R,4S,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-4-(tert-butyldimethylsiloxy)-N-(isoxazol-4-yl)-6-phenylhexanamide

Base Information

• Chemical Name: (2R,4S,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-4-(tert-butyldimethylsiloxy)-N-(isoxazol-4-yl)-6-phenylhexanamide
• CAS No.: 149976-34-1
• Molecular Formula: C₃₃H₄₇N₃O₅Si
• Molecular Weight: 593.839
• Mol file: 149976-34-1.mol

Synonyms:(2R,4S,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-4-(tert-butyldimethylsiloxy)-N-(isoxazol-4-yl)-6-phenylhexanamide

Chemical Property of (2R,4S,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-4-(tert-butyldimethylsiloxy)-N-(isoxazol-4-yl)-6-phenylhexanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-4-(tert-butyldimethylsiloxy)-N-(isoxazol-4-yl)-6-phenylhexanamide

There total 1 articles about (2R,4S,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-4-(tert-butyldimethylsiloxy)-N-(isoxazol-4-yl)-6-phenylhexanamide 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: 57.0%

N-(1,1-dimethylethoxycarbonyl)-5(S)-amino-4(S)-(t-butyldimethylsilyloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoic acid (98818-51-0) + isooxazolyl-4-amine (108511-97-3) → (2R,4S,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-4-(tert-butyldimethylsiloxy)-N-(isoxazol-4-yl)-6-phenylhexanamide (149976-34-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.1021/jm00045a015

Reference yield:

(2R,4S,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-4-(tert-butyldimethylsiloxy)-N-(isoxazol-4-yl)-6-phenylhexanamide (149976-34-1) → 2-<(1R,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-phenylpentyl>-5-(2-methylpropionyl)imidazole (150349-13-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) H₂, 2.) NaOH / 1.) palladium black / 1.) EtOH, 23 h, 2.) EtOH, reflux, 3 h

2: 93 percent / tetrahydrofuran; diethyl ether / 0.25 h

3: 90 percent / MnO₂ / CH₂Cl₂ / Ambient temperature

4: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 50 °C

5: 100 percent / TFA / 0.08 h / Ambient temperature

With manganese(IV) oxide; sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; trifluoroacetic acid; palladium; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jm00045a015

Reference yield:

(2R,4S,5S)-2-benzyl-5-<(tert-butoxycarbonyl)amino>-4-(tert-butyldimethylsiloxy)-N-(isoxazol-4-yl)-6-phenylhexanamide (149976-34-1) → [(1S,2S,4R)-1-Benzyl-4-(5-formyl-1H-imidazol-2-yl)-2-hydroxy-5-phenyl-pentyl]-carbamic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) H₂, 2.) NaOH / 1.) palladium black / 1.) EtOH, 23 h, 2.) EtOH, reflux, 3 h

2: 66 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 5 h / 50 °C

With sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; palladium; In tetrahydrofuran;

DOI:10.1021/jm00045a015

upstream raw materials:

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

isooxazolyl-4-amine

Downstream raw materials:

2-<(2R,3S,4S)-1-benzyl-4-<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsiloxy)-5-phenylpentyl>-5-formylimidazole

2-<(1R,3S,4S)-4-amino-1-benzyl-3-hydroxy-5-phenylpentyl>-5-(2-methylpropionyl)imidazole

[(1S,2S,4R)-1-Benzyl-2-hydroxy-4-(5-isobutyryl-1H-imidazol-2-yl)-5-phenyl-pentyl]-carbamic acid tert-butyl ester

[(1S,2S,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-4-(5-propionyl-1H-imidazol-2-yl)-pentyl]-carbamic acid tert-butyl ester

Refernces