tert-butyl 3,9-bis(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1⁽¹⁵⁾,11,13-triene-6-acetate

Base Information

• Chemical Name: tert-butyl 3,9-bis(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1⁽¹⁵⁾,11,13-triene-6-acetate
• CAS No.: 353246-06-7
• Molecular Formula: C₂₉H₃₄N₆O₁₀S₂
• Molecular Weight: 690.755

Synonyms:tert-butyl 3,9-bis(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1⁽¹⁵⁾,11,13-triene-6-acetate

Chemical Property of tert-butyl 3,9-bis(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1⁽¹⁵⁾,11,13-triene-6-acetate

Chemical Property:

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Technology Process of tert-butyl 3,9-bis(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1⁽¹⁵⁾,11,13-triene-6-acetate

There total 3 articles about tert-butyl 3,9-bis(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1⁽¹⁵⁾,11,13-triene-6-acetate 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: 58.0%

2,6-bis-(bromomethyl)pyridine (7703-74-4) + 4-((tert-butoxycarbonyl)methyl)-1,7-bis(2-nitrophenylsulfonyl)-1,4,7-triazaheptane (353246-03-4) → tert-butyl 3,9-bis(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-acetate (353246-06-7)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1016/S0040-4020(01)00328-3

Reference yield:

2-Nitrobenzenesulfonyl chloride (1694-92-4) → tert-butyl 3,9-bis(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-acetate (353246-06-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / NaHCO₃ / tetrahydrofuran / 12 h / 20 °C

2: 82 percent / Et₃N / tetrahydrofuran / Heating

3: 58 percent / Na₂CO₃ / dimethylformamide / 100 °C

With sodium hydrogencarbonate; sodium carbonate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 3: Richman-Atkins cyclization;

DOI:10.1016/S0040-4020(01)00328-3

Reference yield:

2-nitro-[N-(2{2[(2-nitrophenyl)sulfonylamino]ethylamino})ethyl]benzenesulfonamide (290325-99-4) → tert-butyl 3,9-bis(2-nitrophenylsulfonyl)-3,6,9,15-tetraazabicyclo[9.3.1]pentadecane-1(15),11,13-triene-6-acetate (353246-06-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / Et₃N / tetrahydrofuran / Heating

2: 58 percent / Na₂CO₃ / dimethylformamide / 100 °C

With sodium carbonate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 2: Richman-Atkins cyclization;

DOI:10.1016/S0040-4020(01)00328-3

upstream raw materials:

2,6-bis-(bromomethyl)pyridine

4-((tert-butoxycarbonyl)methyl)-1,7-bis(2-nitrophenylsulfonyl)-1,4,7-triazaheptane

2-Nitrobenzenesulfonyl chloride

2-nitro-[N-(2{2[(2-nitrophenyl)sulfonylamino]ethylamino})ethyl]benzenesulfonamide

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