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

Base Information

• Chemical Name: (S)-benzyloxycarbonylalanyl-(S)-(Nδ-tert-butyloxycarbonyl)-ornithine 4-(tert-butoxycarbonyl)phenylmethyl ester
• CAS No.: 1350629-67-2
• Molecular Formula: C₃₃H₄₅N₃O₉
• Molecular Weight: 627.735
• Mol file: 1350629-67-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (S)-benzyloxycarbonylalanyl-(S)-(Nδ-tert-butyloxycarbonyl)-ornithine 4-(tert-butoxycarbonyl)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:

N-Cbz-Ala (1142-20-7) + C22H34N2O6 → (S)-benzyloxycarbonylalanyl-(S)-(Nδ-tert-butyloxycarbonyl)-ornithine 4-(tert-butoxycarbonyl)phenylmethyl ester (1350629-67-2)

Guidance literature:

N-Cbz-Ala; With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

C₂₂H₃₄N₂O₆; With trimethyl phosphite; In dichloromethane; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c1ob05661a

Reference yield:

terephthalic acid mono-tert-butyl ester (20576-82-3) → (S)-benzyloxycarbonylalanyl-(S)-(Nδ-tert-butyloxycarbonyl)-ornithine 4-(tert-butoxycarbonyl)phenylmethyl ester (1350629-67-2)

Guidance literature:

Multi-step reaction with 4 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

With 1-hydroxy-7-aza-benzotriazole; tetrabutylammonium borohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 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) → (S)-benzyloxycarbonylalanyl-(S)-(Nδ-tert-butyloxycarbonyl)-ornithine 4-(tert-butoxycarbonyl)phenylmethyl ester (1350629-67-2)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1039/c1ob05661a

upstream raw materials:

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

N-Cbz-Ala

di-tert-butyl terephthalate

terephthalic acid mono-tert-butyl ester

Downstream raw materials:

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

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