3,9-bis(p-toluenesulfonyl)-3,6,9,15-tetraazabicyclo[11.3.1]pentadeca-1⁽¹⁵⁾,11,13-triene

Base Information

• Chemical Name: 3,9-bis(p-toluenesulfonyl)-3,6,9,15-tetraazabicyclo[11.3.1]pentadeca-1⁽¹⁵⁾,11,13-triene
• CAS No.: 170862-19-8
• Molecular Formula: C₂₅H₃₀N₄O₄S₂
• Molecular Weight: 514.67

Synonyms:3,9-bis(p-toluenesulfonyl)-3,6,9,15-tetraazabicyclo[11.3.1]pentadeca-1⁽¹⁵⁾,11,13-triene

Chemical Property of 3,9-bis(p-toluenesulfonyl)-3,6,9,15-tetraazabicyclo[11.3.1]pentadeca-1⁽¹⁵⁾,11,13-triene

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Technology Process of 3,9-bis(p-toluenesulfonyl)-3,6,9,15-tetraazabicyclo[11.3.1]pentadeca-1⁽¹⁵⁾,11,13-triene

There total 4 articles about 3,9-bis(p-toluenesulfonyl)-3,6,9,15-tetraazabicyclo[11.3.1]pentadeca-1⁽¹⁵⁾,11,13-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: 80.0%

[3,9-bis-(toluene-4-sulfonyl)-3,6,9,15-tetraaza-bicyclo[9.3.1]pentadeca-1(14),11(15),12-trien-6-yl]-phosphonic acid diethyl ester → 3,9-bis(p-toluenesulfonyl)-3,6,9,15-tetraazabicyclo[11.3.1]pentadeca-1(15),11,13-triene (170862-19-8)

Guidance literature:

With hydrogen bromide; acetic acid; at 20 ℃; for 2h;

DOI:10.1021/jm990211i

Reference yield:

2,6-bis-(bromomethyl)pyridine hydrobromide (73004-40-7) → 3,9-bis(p-toluenesulfonyl)-3,6,9,15-tetraazabicyclo[11.3.1]pentadeca-1(15),11,13-triene (170862-19-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / Cs₂CO₃ / dimethylformamide / 24 h / 65 °C

2: 80 percent / glac. AcOH, HBr / 2 h / 20 °C

With hydrogen bromide; caesium carbonate; acetic acid; In N,N-dimethyl-formamide; 1: cyclocondensation / 2: diethoxyphosphoryl deprotection;

DOI:10.1021/jm990211i

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 3,9-bis(p-toluenesulfonyl)-3,6,9,15-tetraazabicyclo[11.3.1]pentadeca-1(15),11,13-triene (170862-19-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂

2: 68 percent / Cs₂CO₃ / dimethylformamide / 24 h / 65 °C

3: 80 percent / glac. AcOH, HBr / 2 h / 20 °C

With hydrogen bromide; caesium carbonate; acetic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Tosylation / 2: cyclocondensation / 3: diethoxyphosphoryl deprotection;

DOI:10.1021/jm990211i

upstream raw materials:

2,6-bis-(bromomethyl)pyridine hydrobromide

p-toluenesulfonyl chloride

bis-[2-(toluene-4-sulfonylamino)-ethyl]-phosphoramidic acid diethyl ester

Downstream raw materials:

C₅₈H₆₆N₈O₈S₄

C₅₈H₆₆N₈O₈S₄

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