N-[N^2',N^6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide

Base Information

• Chemical Name: N-[N^2',N^6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide
• CAS No.: 439152-26-8
• Molecular Formula: C₄₆H₅₂N₄O₁₆
• Molecular Weight: 916.936

Synonyms:N-[N^2',N^6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide

Chemical Property of N-[N^2',N^6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide

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Technology Process of N-[N^2',N^6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide

There total 6 articles about N-[N^2',N^6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide 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: 50.0%

L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide (452303-38-7) + N2,N6-bis(2,3-diacetoxybenzoyl)-L-lysine (201296-82-4) → N-[N2',N6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide (439152-26-8)

Guidance literature:

N²,N⁶-bis(2,3-diacetoxybenzoyl)-L-lysine; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -10 ℃; for 0.75h;

L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide; With triethylamine; In tetrahydrofuran; at -10 - 20 ℃; for 2h;

DOI:10.1016/S0968-0896(02)00044-5

Reference yield:

N-cyclohexyl-O-benzoylhydroxylamine (1485-75-2) → N-[N2',N6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide (439152-26-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: i-BuOCOCl; N-methylmorpholine / tetrahydrofuran / 0.75 h / -10 °C

1.2: Et₃N / tetrahydrofuran / 2 h / -10 - 20 °C

2.1: H₂ / 10 percent Pd/C / 20 °C / atmospheric pressure

3.1: i-BuOCOCl; N-methylmorpholine / tetrahydrofuran / 0.75 h / -10 °C

3.2: 50 percent / Et₃N / tetrahydrofuran / 2 h / -10 - 20 °C

With 4-methyl-morpholine; hydrogen; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/S0968-0896(02)00044-5

Reference yield:

Cbz-(L)-Glu-OBn (3705-42-8) → N-[N2',N6'-bis(2,3-diacetoxybenzoyl)-L-lysyl]-L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide (439152-26-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: i-BuOCOCl; N-methylmorpholine / tetrahydrofuran / 0.75 h / -10 °C

1.2: Et₃N / tetrahydrofuran / 2 h / -10 - 20 °C

2.1: H₂ / 10 percent Pd/C / 20 °C / atmospheric pressure

3.1: i-BuOCOCl; N-methylmorpholine / tetrahydrofuran / 0.75 h / -10 °C

3.2: 50 percent / Et₃N / tetrahydrofuran / 2 h / -10 - 20 °C

With 4-methyl-morpholine; hydrogen; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/S0968-0896(02)00044-5

upstream raw materials:

L-glutamic acid 5-(N-benzyloxy-N-cyclohexyl)amide

N²,N⁶-bis(2,3-diacetoxybenzoyl)-L-lysine

L-lysine

N-cyclohexyl-O-benzoylhydroxylamine

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