3,12,20-tris(2-nitrobenzenesulfonyl)-7-(tert-butoxycarbonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.1^1,22.1^14,18]heptacosa-1⁽²⁶⁾,14⁽²⁷⁾,15,17,22,24-hexaene

Base Information

• Chemical Name: 3,12,20-tris(2-nitrobenzenesulfonyl)-7-(tert-butoxycarbonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.1^1,22.1^14,18]heptacosa-1⁽²⁶⁾,14⁽²⁷⁾,15,17,22,24-hexaene
• CAS No.: 211512-25-3
• Molecular Formula: C₄₄H₄₉N₉O₁₄S₃
• Molecular Weight: 1024.12

Synonyms:3,12,20-tris(2-nitrobenzenesulfonyl)-7-(tert-butoxycarbonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.1^1,22.1^14,18]heptacosa-1⁽²⁶⁾,14⁽²⁷⁾,15,17,22,24-hexaene

Chemical Property of 3,12,20-tris(2-nitrobenzenesulfonyl)-7-(tert-butoxycarbonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.1^1,22.1^14,18]heptacosa-1⁽²⁶⁾,14⁽²⁷⁾,15,17,22,24-hexaene

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Technology Process of 3,12,20-tris(2-nitrobenzenesulfonyl)-7-(tert-butoxycarbonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.1^1,22.1^14,18]heptacosa-1⁽²⁶⁾,14⁽²⁷⁾,15,17,22,24-hexaene

There total 4 articles about 3,12,20-tris(2-nitrobenzenesulfonyl)-7-(tert-butoxycarbonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.1^1,22.1^14,18]heptacosa-1⁽²⁶⁾,14⁽²⁷⁾,15,17,22,24-hexaene 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: 63.0%

[4-(2-Nitro-benzenesulfonylamino)-butyl]-[3-(2-nitro-benzenesulfonylamino)-propyl]-carbamic acid tert-butyl ester (182576-26-7) + N,N-bis{[6-(p-tosyloxymethyl)pyridin-2-yl]methyl}-2-nitrobenzenesulfonamide (211512-10-6) → 3,12,20-tris(2-nitrobenzenesulfonyl)-7-(tert-butoxycarbonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.11,22.114,18]heptacosa-1(26),14(27),15,17,22,24-hexaene (211512-25-3)

Guidance literature:

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

DOI:10.1016/S0040-4020(98)00441-4

Reference yield:

2.6-bis(hydroxymethyl)pyridine (1195-59-1) → 3,12,20-tris(2-nitrobenzenesulfonyl)-7-(tert-butoxycarbonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.11,22.114,18]heptacosa-1(26),14(27),15,17,22,24-hexaene (211512-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: PPh₃ / tetrahydrofuran / 0.5 h / 20 °C

1.2: 34 percent / tetrahydrofuran / 20 °C

2.1: 89 percent / NaOH / tetrahydrofuran; H₂O / 3 h / 0 - 20 °C

3.1: 63 percent / Cs₂CO₃ / dimethylformamide / 20 °C

With sodium hydroxide; caesium carbonate; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide; 1.1: Condensation / 1.2: Substitution / 2.1: Tosylation / 3.1: Cyclization;

DOI:10.1016/S0040-4020(98)00441-4

Reference yield:

2-Nitrobenzenesulfonamide (5455-59-4) → 3,12,20-tris(2-nitrobenzenesulfonyl)-7-(tert-butoxycarbonyl)-3,7,12,20,26,27-hexaazatricyclo[20.3.11,22.114,18]heptacosa-1(26),14(27),15,17,22,24-hexaene (211512-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: PPh₃ / tetrahydrofuran / 0.5 h / 20 °C

1.2: 34 percent / tetrahydrofuran / 20 °C

2.1: 89 percent / NaOH / tetrahydrofuran; H₂O / 3 h / 0 - 20 °C

3.1: 63 percent / Cs₂CO₃ / dimethylformamide / 20 °C

With sodium hydroxide; caesium carbonate; triphenylphosphine; In tetrahydrofuran; water; N,N-dimethyl-formamide; 1.1: Condensation / 1.2: Substitution / 2.1: Tosylation / 3.1: Cyclization;

DOI:10.1016/S0040-4020(98)00441-4

upstream raw materials:

[4-(2-Nitro-benzenesulfonylamino)-butyl]-[3-(2-nitro-benzenesulfonylamino)-propyl]-carbamic acid tert-butyl ester

N,N-bis{[6-(p-tosyloxymethyl)pyridin-2-yl]methyl}-2-nitrobenzenesulfonamide

2.6-bis(hydroxymethyl)pyridine

2-Nitrobenzenesulfonamide

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