N¹-(4-nitrobenzo-6-oxa-5,7-diazolyl)-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-N^g-tosyl-N^α-methylarginyl-D-leucyl)-1,8-octanediamine

Base Information

• Chemical Name: N¹-(4-nitrobenzo-6-oxa-5,7-diazolyl)-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-N^g-tosyl-N^α-methylarginyl-D-leucyl)-1,8-octanediamine
• CAS No.: 212716-37-5
• Molecular Formula: C₅₂H₇₈N₁₄O₁₂S₂
• Molecular Weight: 1155.41

Synonyms:N¹-(4-nitrobenzo-6-oxa-5,7-diazolyl)-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-N^g-tosyl-N^α-methylarginyl-D-leucyl)-1,8-octanediamine

Chemical Property of N¹-(4-nitrobenzo-6-oxa-5,7-diazolyl)-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-N^g-tosyl-N^α-methylarginyl-D-leucyl)-1,8-octanediamine

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Technology Process of N¹-(4-nitrobenzo-6-oxa-5,7-diazolyl)-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-N^g-tosyl-N^α-methylarginyl-D-leucyl)-1,8-octanediamine

There total 8 articles about N¹-(4-nitrobenzo-6-oxa-5,7-diazolyl)-N⁸-(N^α-t-butoxycarbonyl-N^g-tosylarginyl-N^g-tosyl-N^α-methylarginyl-D-leucyl)-1,8-octanediamine 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: 81.8%

NBD chloride (10199-89-0) + C46H77N11O9S2 → N1-(4-nitrobenzo-6-oxa-5,7-diazolyl)-N8-(Nα-t-butoxycarbonyl-Ng-tosylarginyl-Ng-tosyl-Nα-methylarginyl-D-leucyl)-1,8-octanediamine (212716-37-5)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; methanol; Ambient temperature;

DOI:10.1016/S0968-0896(98)00031-5

Reference yield:

N-Boc-D-Leu (16937-99-8,53296-34-7) → N1-(4-nitrobenzo-6-oxa-5,7-diazolyl)-N8-(Nα-t-butoxycarbonyl-Ng-tosylarginyl-Ng-tosyl-Nα-methylarginyl-D-leucyl)-1,8-octanediamine (212716-37-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 97.8 percent / DCC, TEA, HOBt / dimethylformamide / Ambient temperature

2: 1.) TFA, 2.) NaHCO₃ / 1.) CH₂Cl₂, 2 h, 2.) AcOEt

3: 93 percent / HOBt, EDC*HCl / dimethylformamide / 1.) 0 deg C, 10 min, 2.) room temperature, overnight

4: 1.) TFA, 2.) NaHCO₃ / 1.) CH₂Cl₂, 2 h, 2.) AcOEt

5: 1.) EDC*HCl / 1.) DMF, -20 deg C, 100 min, 2.) DMF, room temperature, overnight

6: H₂, AcOH / Pd-black / methanol / 1.5 h

7: 81.8 percent / NaHCO₃ / tetrahydrofuran; methanol / Ambient temperature

With TEA; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(98)00031-5

Reference yield:

N1-benzyloxycarbonyl-N8-D-leucyl-1,8-octanediamine (175216-23-6) → N1-(4-nitrobenzo-6-oxa-5,7-diazolyl)-N8-(Nα-t-butoxycarbonyl-Ng-tosylarginyl-Ng-tosyl-Nα-methylarginyl-D-leucyl)-1,8-octanediamine (212716-37-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / HOBt, EDC*HCl / dimethylformamide / 1.) 0 deg C, 10 min, 2.) room temperature, overnight

2: 1.) TFA, 2.) NaHCO₃ / 1.) CH₂Cl₂, 2 h, 2.) AcOEt

3: 1.) EDC*HCl / 1.) DMF, -20 deg C, 100 min, 2.) DMF, room temperature, overnight

4: H₂, AcOH / Pd-black / methanol / 1.5 h

5: 81.8 percent / NaHCO₃ / tetrahydrofuran; methanol / Ambient temperature

With hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(98)00031-5

upstream raw materials:

NBD chloride

N-Boc-D-Leu

N¹-benzyloxycarbonyl-N⁸-D-leucyl-1,8-octanediamine

N¹-benzyloxycarbonyl-N⁸-(t-butoxycarbonyl-D-leucyl)-1,8-octanediamine

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