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

Base Information

• Chemical Name: 2-<(2R,3S,4S)-1-benzyl-4-<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsiloxy)-5-phenylpentyl>-5-formylimidazole
• CAS No.: 159949-20-9
• Molecular Formula: C₃₃H₄₇N₃O₄Si
• Molecular Weight: 577.839

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

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

Chemical Property:

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

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

N-(1,1-dimethylethoxycarbonyl)-5(S)-amino-4(S)-(t-butyldimethylsilyloxy)-6-phenyl-2(R)-(phenylmethyl)hexanoic acid (98818-51-0) → 2-<(2R,3S,4S)-1-benzyl-4-<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsiloxy)-5-phenylpentyl>-5-formylimidazole (159949-20-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / 1-hydroxybenzotriazole, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 24 h / Ambient temperature

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

With sodium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium; In N,N-dimethyl-formamide;

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-<(2R,3S,4S)-1-benzyl-4-<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsiloxy)-5-phenylpentyl>-5-formylimidazole (159949-20-9)

Guidance literature:

With sodium hydroxide; hydrogen; palladium; Multistep reaction; 1.) EtOH, 23 h, 2.) EtOH, reflux, 3 h;

DOI:10.1021/jm00045a015

Reference yield: 93.0%

isopropylmagnesium bromide (920-39-8) + 2-<(2R,3S,4S)-1-benzyl-4-<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsiloxy)-5-phenylpentyl>-5-formylimidazole (159949-20-9) → 2-<(1R,3S,4S)-1-benzyl-4<(tert-butoxycarbonyl)amino>-3-(tert-butyldimethylsiloxy)-5-phenylpentyl>-5-(1-hydroxy-2-methylpropyl)imidazole (541552-04-9)

Guidance literature:

In tetrahydrofuran; diethyl ether; for 0.25h;

DOI:10.1021/jm00045a015

upstream raw materials:

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

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

Downstream raw materials:

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

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

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

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

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