methyl 8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoate

Base Information

• Chemical Name: methyl 8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoate
• CAS No.: 437718-37-1
• Molecular Formula: C₂₂H₂₇N₃O₈S
• Molecular Weight: 493.538
• Mol file: 437718-37-1.mol

Synonyms:methyl 8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoate

Chemical Property of methyl 8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoate

There total 1 articles about methyl 8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoate 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:

N-(4-aminobutan-1-yl)-2-nitrobenzenesulfonamide (211512-13-9) → methyl 8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoate (437718-37-1)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 5 h / 20 °C

2: 775 mg / Et₃N / toluene / 2 h / 20 °C

With triethylamine; In ethanol; toluene;

DOI:10.1016/j.tet.2006.06.051

Reference yield: 96.0%

methyl 8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoate (437718-37-1) → 8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoic acid (437718-21-3)

Guidance literature:

With sodium hydroxide; In methanol; at 0 - 20 ℃; for 1h;

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

Reference yield:

methyl 8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoate (437718-37-1) → JSTX 3 (112163-33-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 96 percent / aq. NaOH / methanol / 1 h / 0 - 20 °C

2: DCC / CH₂Cl₂ / 5 h / 0 °C

3: dimethylformamide / 0.5 h / 20 °C

4: 92 percent / Cs₂CO₃ / dimethylformamide / 1 h / 50 °C

5: TFA / CHCl₃ / 1 h / 0 - 20 °C

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

7: 2-mercaptoethanol; DBU / dimethylformamide / 0.5 h / 20 °C

8: H₂; AcOH / Pd(OH)2 / 3 h / 20 °C

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

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

upstream raw materials:

N-(4-aminobutan-1-yl)-2-nitrobenzenesulfonamide

Downstream raw materials:

8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoic acid

N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-[8-((2-nitrobenzenesulfonyl)amino)-4-(benzyloxycarbonyl)-4-azaoctanoyl]-1,5-diaminopentane

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

N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-[8-(N^α,N^δ,N^ω-tri(benzyloxycarbonyl)arginylamino)-4-(benzyloxycarbonyl)-4-azaoctanoyl]-1,5-diaminopentane

Refernces

• 1、 Nihei, Ken-Ichi,Kato, Massuo J.,Yamane, Tetsuo,Palma, Mario S.,Konno, Katsuhiro. "An efficient and versatile synthesis of acylpolyamine spider toxins". . p. 299 - 302. Retrieved 2007/10/03.