14-[5-(tert-butoxycarbonyl)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-(tert-butoxycarbonyl)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.: 221298-16-4
• Molecular Formula: C₄₀H₄₈N₈O₁₅S₃
• Molecular Weight: 977.064

Synonyms:14-[5-(tert-butoxycarbonyl)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-(tert-butoxycarbonyl)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-(tert-butoxycarbonyl)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 6 articles about 14-[5-(tert-butoxycarbonyl)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: 89.0%

N1,N3,N6-tris(2-nitrobenzenesulfonyl)-1,6-diamino-3-azahexane (211512-11-7) + 4-[5-(tert-butoxycarbonyl)amino-1-pentanoxyl]pyridine-2,6-dimethyl ditosylate (221298-14-2) → 14-[5-(tert-butoxycarbonyl)amino-1-pentanoxyl]-3,6,10-tris(2-nitrobenzenesulfonyl)-3,6,10,16-tetraazabicyclo[10.3.1]hexadeca-1(16),12,14-triene (221298-16-4)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/jhet.5570370403

Reference yield:

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

Guidance literature:

Multi-step reaction with 4 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

With sodium hydroxide; sodium tetrahydroborate; caesium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 1: Alkylation / 2: Reduction / 3: Tosylation / 4: cyclocondensation;

DOI:10.1002/jhet.5570370403

Reference yield:

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

Guidance literature:

Multi-step reaction with 4 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

With sodium hydroxide; sodium tetrahydroborate; caesium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 1: Alkylation / 2: Reduction / 3: Tosylation / 4: cyclocondensation;

DOI:10.1002/jhet.5570370403

upstream raw materials:

N¹,N³,N⁶-tris(2-nitrobenzenesulfonyl)-1,6-diamino-3-azahexane

4-[5-(tert-butoxycarbonyl)amino-1-pentanoxyl]pyridine-2,6-dimethyl ditosylate

dimethyl 4-hydroxypyridine-2,6-dicarboxylate

N-(tert-butyloxycarbonyl)-5-aminopentanol

Downstream raw materials:

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

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

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