N^α-{[(2R-N-benzyloxy-N-formylamino)methyl]-6-heptenoyl}-N-(10-undecen-1-yl)-N^ε-tert-butoxycarbonyl-L-lysinamide

Base Information

• Chemical Name: N^α-{[(2R-N-benzyloxy-N-formylamino)methyl]-6-heptenoyl}-N-(10-undecen-1-yl)-N^ε-tert-butoxycarbonyl-L-lysinamide
• CAS No.: 774226-91-4
• Molecular Formula: C₃₈H₆₂N₄O₆
• Molecular Weight: 670.933

Synonyms:N^α-{[(2R-N-benzyloxy-N-formylamino)methyl]-6-heptenoyl}-N-(10-undecen-1-yl)-N^ε-tert-butoxycarbonyl-L-lysinamide

Chemical Property of N^α-{[(2R-N-benzyloxy-N-formylamino)methyl]-6-heptenoyl}-N-(10-undecen-1-yl)-N^ε-tert-butoxycarbonyl-L-lysinamide

Chemical Property:

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Technology Process of N^α-{[(2R-N-benzyloxy-N-formylamino)methyl]-6-heptenoyl}-N-(10-undecen-1-yl)-N^ε-tert-butoxycarbonyl-L-lysinamide

There total 6 articles about N^α-{[(2R-N-benzyloxy-N-formylamino)methyl]-6-heptenoyl}-N-(10-undecen-1-yl)-N^ε-tert-butoxycarbonyl-L-lysinamide 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: 85.0%

2R-[(N-benzyloxy-N-formylamino)methyl]-6-heptenoic acid (596111-53-4) + N-(10-undecen-1-yl)-Nε-tert-butoxycarbonyl-L-lysinamide (774226-89-0) → Nα-{[(2R-N-benzyloxy-N-formylamino)methyl]-6-heptenoyl}-N-(10-undecen-1-yl)-Nε-tert-butoxycarbonyl-L-lysinamide (774226-91-4)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane;

DOI:10.1021/jm049592c

Reference yield:

undec-10-en-1-amine (62595-52-2) → Nα-{[(2R-N-benzyloxy-N-formylamino)methyl]-6-heptenoyl}-N-(10-undecen-1-yl)-Nε-tert-butoxycarbonyl-L-lysinamide (774226-91-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / triethylamine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 2 h

2: 87 percent / piperidine / CH₂Cl₂ / 0.67 h

3: 85 percent / triethylamine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂

With piperidine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane;

DOI:10.1021/jm049592c

Reference yield:

10-Undecen-1-ol (112-43-6) → Nα-{[(2R-N-benzyloxy-N-formylamino)methyl]-6-heptenoyl}-N-(10-undecen-1-yl)-Nε-tert-butoxycarbonyl-L-lysinamide (774226-91-4)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / CH₂Cl₂ / 2 h

2: aq. sodium azide / dimethylformamide / 50 °C

3: LiAlH₄ / diethyl ether

4: 82 percent / triethylamine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 2 h

5: 87 percent / piperidine / CH₂Cl₂ / 0.67 h

6: 85 percent / triethylamine; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂

With piperidine; lithium aluminium tetrahydride; sodium azide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm049592c

upstream raw materials:

2R-[(N-benzyloxy-N-formylamino)methyl]-6-heptenoic acid

N-(10-undecen-1-yl)-N^ε-tert-butoxycarbonyl-L-lysinamide

undec-10-en-1-amine

10-Undecen-1-ol

Downstream raw materials:

N-{3-[4-(tert-butoxycarbonylamino)butyl]-2,5-dioxo-1,4-diazacycloicos-10-en-6-yl}methyl-N-benzyloxyformamide

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