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

Base Information

• Chemical Name: 14-[5-(1-pyrenecarbonyl)amino-1-pentanoxyl]-3,6,10-tris(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1⁽¹⁶⁾,12,14-triene
• CAS No.: 221298-18-6
• Molecular Formula: C₅₂H₄₈N₈O₁₄S₃
• Molecular Weight: 1105.2

Synonyms:14-[5-(1-pyrenecarbonyl)amino-1-pentanoxyl]-3,6,10-tris(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1⁽¹⁶⁾,12,14-triene

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

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

There total 8 articles about 14-[5-(1-pyrenecarbonyl)amino-1-pentanoxyl]-3,6,10-tris(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: 71.0%

Pyrene-1-carboxylic acid (19694-02-1) + 14-(5-amino-1-pentanoxyl)-3,6,10-tris(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (221298-17-5) → 14-[5-(1-pyrenecarbonyl)amino-1-pentanoxyl]-3,6,10-tris(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (221298-18-6)

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:

dimethyl 4-hydroxypyridine-2,6-dicarboxylate (19872-91-4) → 14-[5-(1-pyrenecarbonyl)amino-1-pentanoxyl]-3,6,10-tris(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (221298-18-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / PPh₃; DEAD / tetrahydrofuran / 24 h / 20 °C

2: 76 percent / NaBH₄ / ethanol / 2 h / Heating

3: 96 percent / aq. NaOH / tetrahydrofuran / 4 h / 20 °C

4: 89 percent / Cs₂CO₃ / dimethylformamide / 20 °C

5: 28 percent / TFA / CH₂Cl₂ / 20 °C

6: 71 percent / DCC; HOBT; 4-methylmorpholine / dimethylformamide; acetonitrile / 40 h / 20 °C

With 4-methyl-morpholine; sodium hydroxide; sodium tetrahydroborate; benzotriazol-1-ol; caesium carbonate; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Alkylation / 2: Reduction / 3: Tosylation / 4: cyclocondensation / 5: acidolysis / 6: Acylation;

DOI:10.1002/jhet.5570370403

Reference yield:

N-(tert-butyloxycarbonyl)-5-aminopentanol (75178-90-4) → 14-[5-(1-pyrenecarbonyl)amino-1-pentanoxyl]-3,6,10-tris(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (221298-18-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / PPh₃; DEAD / tetrahydrofuran / 24 h / 20 °C

2: 76 percent / NaBH₄ / ethanol / 2 h / Heating

3: 96 percent / aq. NaOH / tetrahydrofuran / 4 h / 20 °C

4: 89 percent / Cs₂CO₃ / dimethylformamide / 20 °C

5: 28 percent / TFA / CH₂Cl₂ / 20 °C

6: 71 percent / DCC; HOBT; 4-methylmorpholine / dimethylformamide; acetonitrile / 40 h / 20 °C

With 4-methyl-morpholine; sodium hydroxide; sodium tetrahydroborate; benzotriazol-1-ol; caesium carbonate; dicyclohexyl-carbodiimide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Alkylation / 2: Reduction / 3: Tosylation / 4: cyclocondensation / 5: acidolysis / 6: Acylation;

DOI:10.1002/jhet.5570370403

upstream raw materials:

Pyrene-1-carboxylic acid

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

dimethyl 4-hydroxypyridine-2,6-dicarboxylate

N-(tert-butyloxycarbonyl)-5-aminopentanol

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