4,8-bis(benzyloxycarbonyl)-N¹-[4,N⁸-bis(benzyloxycarbonyl)-8-amino-4-azaoctanoyl]-N¹²-{N^α-[2,4-bis(benzyloxy)phenylacetyl]asparaginyl}-4,8-diaza-1,12-dodecanediamine

Base Information

• Chemical Name: 4,8-bis(benzyloxycarbonyl)-N¹-[4,N⁸-bis(benzyloxycarbonyl)-8-amino-4-azaoctanoyl]-N¹²-{N^α-[2,4-bis(benzyloxy)phenylacetyl]asparaginyl}-4,8-diaza-1,12-dodecanediamine
• CAS No.: 679812-62-5
• Molecular Formula: C₇₅H₈₈N₈O₁₄
• Molecular Weight: 1325.57

Synonyms:4,8-bis(benzyloxycarbonyl)-N¹-[4,N⁸-bis(benzyloxycarbonyl)-8-amino-4-azaoctanoyl]-N¹²-{N^α-[2,4-bis(benzyloxy)phenylacetyl]asparaginyl}-4,8-diaza-1,12-dodecanediamine

Chemical Property of 4,8-bis(benzyloxycarbonyl)-N¹-[4,N⁸-bis(benzyloxycarbonyl)-8-amino-4-azaoctanoyl]-N¹²-{N^α-[2,4-bis(benzyloxy)phenylacetyl]asparaginyl}-4,8-diaza-1,12-dodecanediamine

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Technology Process of 4,8-bis(benzyloxycarbonyl)-N¹-[4,N⁸-bis(benzyloxycarbonyl)-8-amino-4-azaoctanoyl]-N¹²-{N^α-[2,4-bis(benzyloxy)phenylacetyl]asparaginyl}-4,8-diaza-1,12-dodecanediamine

There total 11 articles about 4,8-bis(benzyloxycarbonyl)-N¹-[4,N⁸-bis(benzyloxycarbonyl)-8-amino-4-azaoctanoyl]-N¹²-{N^α-[2,4-bis(benzyloxy)phenylacetyl]asparaginyl}-4,8-diaza-1,12-dodecanediamine 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: 90.1%

4,N8-bis(benzyloxycarbonyl)-8-amino-4-azaoctanoic acid succinimidyl ester (345898-23-9) + 4,8-bis(benzyloxycarbonyl)-N12-{Nα-[2,4-bis(benzyloxy)phenylacetyl]asparaginyl}-4,8-diaza-1,12-dodecanediamine acetate → 4,8-bis(benzyloxycarbonyl)-N1-[4,N8-bis(benzyloxycarbonyl)-8-amino-4-azaoctanoyl]-N12-{Nα-[2,4-bis(benzyloxy)phenylacetyl]asparaginyl}-4,8-diaza-1,12-dodecanediamine (679812-62-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1246/bcsj.77.331

Reference yield:

4,8-bis(benzyloxycarbonyl)-N1-(2,2,2-trichloroethoxycarbonyl)-N12-(tert-butoxycarbonyl)-4,8-diaza-1,12-dodecanediamine (345898-28-4) → 4,8-bis(benzyloxycarbonyl)-N1-[4,N8-bis(benzyloxycarbonyl)-8-amino-4-azaoctanoyl]-N12-{Nα-[2,4-bis(benzyloxy)phenylacetyl]asparaginyl}-4,8-diaza-1,12-dodecanediamine (679812-62-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: CF₃CO₂H / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 2.77 g / Et₃N / dimethylformamide / 1 h / 20 °C

3.1: CF₃CO₂H / CH₂Cl₂ / 1.5 h / 20 °C

4.1: 3.10 g / Et₃N / dimethylformamide / 22 h / 20 °C

5.1: Zn / 24 h / 20 °C

5.2: H₂S / 1.5 h / 20 °C

6.1: 90.1 percent / Et₃N / dimethylformamide / 18 h / 20 °C

With triethylamine; trifluoroacetic acid; zinc; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.77.331

Reference yield:

methyl 4-benzyloxycarbonyl-8-hydroxy-4-azaoctanoate (345898-20-6) → 4,8-bis(benzyloxycarbonyl)-N1-[4,N8-bis(benzyloxycarbonyl)-8-amino-4-azaoctanoyl]-N12-{Nα-[2,4-bis(benzyloxy)phenylacetyl]asparaginyl}-4,8-diaza-1,12-dodecanediamine (679812-62-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / 1 h / 0 °C

2.1: 1.33 g / NaN₃ / dimethylformamide / 1 h / 80 °C

3.1: PPh₃ / tetrahydrofuran; H₂O / 20 h / 20 °C

3.2: 79.5 percent / Na₂CO₃ / ethyl acetate; tetrahydrofuran; H₂O / 5 h / 20 °C

4.1: NaOH / methanol; H₂O / 1 h / 60 °C

5.1: EDC*HCl / dimethylformamide / 20 °C

6.1: 90.1 percent / Et₃N / dimethylformamide / 18 h / 20 °C

With pyridine; sodium hydroxide; sodium azide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.77.331

upstream raw materials:

4,N⁸-bis(benzyloxycarbonyl)-8-amino-4-azaoctanoic acid succinimidyl ester

4,8-bis(benzyloxycarbonyl)-N¹-(2,2,2-trichloroethoxycarbonyl)-N¹²-(tert-butoxycarbonyl)-4,8-diaza-1,12-dodecanediamine

methyl 4-benzyloxycarbonyl-8-hydroxy-4-azaoctanoate

methyl 8-azido-4-benzyloxycarbonyl-4-azaoctanoate

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