N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane

Base Information

• Chemical Name: N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane
• CAS No.: 437718-36-0
• Molecular Formula: C₂₀H₃₁N₅O₈S
• Molecular Weight: 501.561

Synonyms:N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane

Chemical Property of N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane

Chemical Property:

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Technology Process of N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane

There total 1 articles about N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane 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: 97.0%

N-(tert-butyloxycarbonyl)-L-asparagine p-nitrophenyl ester (4587-33-1) + mono-2-nitrobenzenesulfonamide-cadaverine HCl salt (437718-20-2) → N-[Nα-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane (437718-36-0)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 0.5h;

DOI:10.1016/S0960-894X(01)00733-8

Reference yield:

N-[Nα-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane (437718-36-0) → JSTX 3 (112163-33-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / 2-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C

2: dimethylformamide / 0.5 h / 20 °C

3: 92 percent / Cs₂CO₃ / dimethylformamide / 1 h / 50 °C

4: TFA / CHCl₃ / 1 h / 0 - 20 °C

5: Et₃N / dimethylformamide / 2 h / 20 °C

6: 2-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C

7: H₂; AcOH / Pd(OH)2 / 3 h / 20 °C

With hydrogen; caesium carbonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; 2-hydroxyethanethiol; palladium dihydroxide; In chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00733-8

Reference yield:

N-[Nα-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane (437718-36-0) → joramine

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / 2-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C

2: dimethylformamide / 0.5 h / 20 °C

3: TFA / CHCl₃ / 1 h / 0 - 20 °C

4: Et₃N / dimethylformamide / 2 h / 20 °C

5: 2-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C

6: H₂; AcOH / Pd(OH)2 / 3 h / 20 °C

With hydrogen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; 2-hydroxyethanethiol; palladium dihydroxide; In chloroform; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00733-8

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-asparagine p-nitrophenyl ester

mono-2-nitrobenzenesulfonamide-cadaverine HCl salt

Downstream raw materials:

{3-[{3-[[5-(2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-pentyl]-(2-nitro-benzenesulfonyl)-amino]-propyl}-(2-nitro-benzenesulfonyl)-amino]-propyl}-carbamic acid allyl ester

C₆₂H₇₈N₁₂O₁₉S₂

{4-[{[5-(2-tert-butoxycarbonylamino-3-carbamoyl-propionylamino)-pentylcarbamoyl]-methyl}-(2-nitro-benzenesulfonyl)-amino]-butyl}-carbamic acid benzyl ester

N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-[7-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaheptanoyl]-1,5-diaminopentane

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