(2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}pentanoic acid 4-(tert-butyloxycarbonyl)phenylmethyl ester

Base Information

• Chemical Name: (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}pentanoic acid 4-(tert-butyloxycarbonyl)phenylmethyl ester
• CAS No.: 1350629-59-2
• Molecular Formula: C₃₆H₄₇N₃O₁₀
• Molecular Weight: 681.783
• Mol file: 1350629-59-2.mol

Synonyms:(2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}pentanoic acid 4-(tert-butyloxycarbonyl)phenylmethyl ester

Chemical Property of (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}pentanoic acid 4-(tert-butyloxycarbonyl)phenylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}pentanoic acid 4-(tert-butyloxycarbonyl)phenylmethyl ester

There total 6 articles about (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}pentanoic acid 4-(tert-butyloxycarbonyl)phenylmethyl ester 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: 35.0%

(S)-benzyloxycarbonylalanyl-(S)-(Nδ-tert-butyloxycarbonyl)-ornithine 4-(tert-butoxycarbonyl)phenylmethyl ester (1350629-67-2) + (2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid (725240-16-4) → (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}pentanoic acid 4-(tert-butyloxycarbonyl)phenylmethyl ester (1350629-59-2)

Guidance literature:

(S)-benzyloxycarbonylalanyl-(S)-(Nδ-tert-butyloxycarbonyl)-ornithine 4-(tert-butoxycarbonyl)phenylmethyl ester; With hydrogenchloride; triethylsilane; In ethyl acetate; for 3h; Inert atmosphere;

(2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid; With trimethyl phosphite; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; Cooling; Inert atmosphere;

DOI:10.1039/c1ob05661a

Reference yield:

terephthalic acid mono-tert-butyl ester (20576-82-3) → (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}pentanoic acid 4-(tert-butyloxycarbonyl)phenylmethyl ester (1350629-59-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tetrabutylammonium borohydride / 18 h / 20 °C / Inert atmosphere

2.1: dicyclohexyl-carbodiimide / dichloromethane; N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

3.1: diethylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

4.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4.2: 16 h / 0 - 20 °C / Inert atmosphere

5.1: hydrogenchloride; triethylsilane / ethyl acetate / 3 h / Inert atmosphere

5.2: 20 °C / Cooling; Inert atmosphere

With hydrogenchloride; triethylsilane; 1-hydroxy-7-aza-benzotriazole; tetrabutylammonium borohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1039/c1ob05661a

Reference yield:

5-tert-butyloxycarbonylamino-(2S)-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid (4-tert-butyloxycarbonylphenyl)methyl ester (1350629-58-1) → (2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}pentanoic acid 4-(tert-butyloxycarbonyl)phenylmethyl ester (1350629-59-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diethylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2.1: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2.2: 16 h / 0 - 20 °C / Inert atmosphere

3.1: hydrogenchloride; triethylsilane / ethyl acetate / 3 h / Inert atmosphere

3.2: 20 °C / Cooling; Inert atmosphere

With hydrogenchloride; triethylsilane; 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1039/c1ob05661a

upstream raw materials:

5-tert-butyloxycarbonylamino-(2S)-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid (4-tert-butyloxycarbonylphenyl)methyl ester

(S)-benzyloxycarbonylalanyl-(S)-(Nδ-tert-butyloxycarbonyl)-ornithine 4-(tert-butoxycarbonyl)phenylmethyl ester

(2R,3S,4S)-2-hydroxy-4-methyl-3-phenylsulfanylcarbonylhexanoic acid

di-tert-butyl terephthalate

Downstream raw materials:

(2S)-[(2S)-benzyloxycarbonylaminopropionylamino]-5-{[(3S)-((1S)-methylpropyl)-4-oxooxetane-(2R)-carbonyl]amino}pentanoic acid 4-carboxylphenylmethyl ester