N-<3,4-bis(benzyloxy)phenethyl>-N^α,N^δ-bis(benzyloxycarbonyl)-N^α-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate

Base Information

• Chemical Name: N-<3,4-bis(benzyloxy)phenethyl>-N^α,N^δ-bis(benzyloxycarbonyl)-N^α-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate
• CAS No.: 144226-18-6
• Molecular Formula: C₅₄H₅₈N₄O₉
• Molecular Weight: 907.076

Synonyms:N-<3,4-bis(benzyloxy)phenethyl>-N^α,N^δ-bis(benzyloxycarbonyl)-N^α-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate

Chemical Property of N-<3,4-bis(benzyloxy)phenethyl>-N^α,N^δ-bis(benzyloxycarbonyl)-N^α-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate

Chemical Property:

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Technology Process of N-<3,4-bis(benzyloxy)phenethyl>-N^α,N^δ-bis(benzyloxycarbonyl)-N^α-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate

There total 11 articles about N-<3,4-bis(benzyloxy)phenethyl>-N^α,N^δ-bis(benzyloxycarbonyl)-N^α-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate 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: 75.0%

2-(3,4-bis (phenylmethoxy)phenyl)ethylamine hydrochloride (1699-56-5) + Nα,Nδ-bis(benzyloxycarbonyl)-Nα-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate (144226-14-2) → N-<3,4-bis(benzyloxy)phenethyl>-Nα,Nδ-bis(benzyloxycarbonyl)-Nα-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate (144226-18-6)

Guidance literature:

With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxybenzotriazol-hydrate; triethylamine; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jm00101a002

Reference yield:

3-[(benzyloxycarbonyl)amino]propanal (65564-05-8) → N-<3,4-bis(benzyloxy)phenethyl>-Nα,Nδ-bis(benzyloxycarbonyl)-Nα-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate (144226-18-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 4-A molecular sieves / CHCl₃ / 5 h

2: NaBH₃CN, HCl / CHCl₃; dioxane

3: sat. aq. Na₂CO₃ / dioxane / 3 h

4: 92 percent / 1N aq. NaOH / methanol / 3 h

5: 75 percent / Et₃N, 1-hydroxybenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDC) / tetrahydrofuran / Ambient temperature

With hydrogenchloride; sodium hydroxide; 4 A molecular sieve; sodium cyanoborohydride; sodium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxybenzotriazol-hydrate; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; chloroform;

DOI:10.1021/jm00101a002

Reference yield:

3-[(N-benzyloxycarbonyl)amino]propanol (34637-22-4) → N-<3,4-bis(benzyloxy)phenethyl>-Nα,Nδ-bis(benzyloxycarbonyl)-Nα-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate (144226-18-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.25 h / -65 °C

2: 4-A molecular sieves / CHCl₃ / 5 h

3: NaBH₃CN, HCl / CHCl₃; dioxane

4: sat. aq. Na₂CO₃ / dioxane / 3 h

5: 92 percent / 1N aq. NaOH / methanol / 3 h

6: 75 percent / Et₃N, 1-hydroxybenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDC) / tetrahydrofuran / Ambient temperature

With hydrogenchloride; sodium hydroxide; oxalyl dichloride; 4 A molecular sieve; sodium cyanoborohydride; sodium carbonate; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxybenzotriazol-hydrate; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; chloroform;

DOI:10.1021/jm00101a002

upstream raw materials:

2-(3,4-bis (phenylmethoxy)phenyl)ethylamine hydrochloride

N^α,N^δ-bis(benzyloxycarbonyl)-N^α-<3-<(benzyloxycarbonyl)amino>propyl>-L-ornithinate

3-[(benzyloxycarbonyl)amino]propanal

3-[(N-benzyloxycarbonyl)amino]propanol

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