6-[5-(2-anthraquinonecarbonyl)amino-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1⁽¹⁶⁾,12,14-triene

Base Information

• Chemical Name: 6-[5-(2-anthraquinonecarbonyl)amino-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1⁽¹⁶⁾,12,14-triene
• CAS No.: 311337-17-4
• Molecular Formula: C₄₄H₄₃N₇O₁₁S₂
• Molecular Weight: 909.998

Synonyms:6-[5-(2-anthraquinonecarbonyl)amino-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1⁽¹⁶⁾,12,14-triene

Chemical Property of 6-[5-(2-anthraquinonecarbonyl)amino-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1⁽¹⁶⁾,12,14-triene

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Technology Process of 6-[5-(2-anthraquinonecarbonyl)amino-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1⁽¹⁶⁾,12,14-triene

There total 6 articles about 6-[5-(2-anthraquinonecarbonyl)amino-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1⁽¹⁶⁾,12,14-triene 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: 76.0%

anthraquinone-2-carboxylic acid (117-78-2) + 6-(5-amino-1-pentanyl)-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (221297-76-3) → 6-[5-(2-anthraquinonecarbonyl)amino-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (311337-17-4)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; acetonitrile; at 20 ℃; for 40h;

DOI:10.1002/jhet.5570370403

Reference yield:

N-(tert-butyloxycarbonyl)-5-aminopentanol (75178-90-4) → 6-[5-(2-anthraquinonecarbonyl)amino-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (311337-17-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 46 percent / aq. NaOH / tetrahydrofuran / 20 °C

2: 57 percent / K₂CO₃ / acetonitrile / 48 h / Heating

3: 87 percent / TFA / CH₂Cl₂ / 20 °C

4: 76 percent / DCC; HOBT; 4-methylmorpholine / dimethylformamide; acetonitrile / 40 h / 20 °C

With 4-methyl-morpholine; sodium hydroxide; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Tosylation / 2: Alkylation / 3: acidolysis / 4: Acylation;

DOI:10.1002/jhet.5570370403

Reference yield:

3,10-Bis-(2-nitro-benzenesulfonyl)-3,6,10,16-tetraaza-bicyclo[10.3.1]hexadeca-1(16),12,14-triene-6-carboxylic acid tert-butyl ester (182576-27-8) → 6-[5-(2-anthraquinonecarbonyl)amino-1-pentanyl]-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (311337-17-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 73 percent / TFA / CH₂Cl₂ / 20 °C

2: 57 percent / K₂CO₃ / acetonitrile / 48 h / Heating

3: 87 percent / TFA / CH₂Cl₂ / 20 °C

4: 76 percent / DCC; HOBT; 4-methylmorpholine / dimethylformamide; acetonitrile / 40 h / 20 °C

With 4-methyl-morpholine; potassium carbonate; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: acidolysis / 2: Alkylation / 3: acidolysis / 4: Acylation;

DOI:10.1002/jhet.5570370403

upstream raw materials:

anthraquinone-2-carboxylic acid

6-(5-amino-1-pentanyl)-3,10-bis(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1⁽¹⁶⁾,12,14-triene

N-(tert-butyloxycarbonyl)-5-aminopentanol

3,10-Bis-(2-nitro-benzenesulfonyl)-3,6,10,16-tetraaza-bicyclo[10.3.1]hexadeca-1⁽¹⁶⁾,12,14-triene-6-carboxylic acid tert-butyl ester

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