N¹,N⁵,N¹⁰,N¹⁴-tetrakis(mesitylenesulfonyl)-N¹-(tert-butyl)-N¹⁴-ethylhomospermine

Base Information

• Chemical Name: N¹,N⁵,N¹⁰,N¹⁴-tetrakis(mesitylenesulfonyl)-N¹-(tert-butyl)-N¹⁴-ethylhomospermine
• CAS No.: 161452-22-8
• Molecular Formula: C₅₄H₈₂N₄O₈S₄
• Molecular Weight: 1043.53

Synonyms:N¹,N⁵,N¹⁰,N¹⁴-tetrakis(mesitylenesulfonyl)-N¹-(tert-butyl)-N¹⁴-ethylhomospermine

Chemical Property of N¹,N⁵,N¹⁰,N¹⁴-tetrakis(mesitylenesulfonyl)-N¹-(tert-butyl)-N¹⁴-ethylhomospermine

Chemical Property:

Purity/Quality:

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Technology Process of N¹,N⁵,N¹⁰,N¹⁴-tetrakis(mesitylenesulfonyl)-N¹-(tert-butyl)-N¹⁴-ethylhomospermine

There total 13 articles about N¹,N⁵,N¹⁰,N¹⁴-tetrakis(mesitylenesulfonyl)-N¹-(tert-butyl)-N¹⁴-ethylhomospermine 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:

2,4,6-Trimethylbenzol-sulfonylisocyanat (21926-49-8) → N1,N5,N10,N14-tetrakis(mesitylenesulfonyl)-N1-(tert-butyl)-N14-ethylhomospermine (161452-22-8)

Guidance literature:

Multi-step reaction with 7 steps

1: various solvent(s) / 8 h / Ambient temperature

2: 1.) NaI, NaH / 1.) DMF, 25 min, 2.) DMF, 70 deg C, 1 d

3: 100 percent / H₂, conc. NH₄OH / Raney Ni / methanol / 6 h / 50 - 55 Torr

4: 87 percent / 1N aq. NaOH / CH₂Cl₂ / 24 h / 0 - 20 °C

5: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, a) 0 deg C, 15 min, b) 70 deg C, overnight

6: 97 percent / TFA / CH₂Cl₂ / 0.83 h / 0 - 20 °C

7: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 70-80 deg C, 8 h

With ammonium hydroxide; sodium hydroxide; hydrogen; sodium hydride; trifluoroacetic acid; sodium iodide; nickel; In methanol; dichloromethane;

DOI:10.1021/jm00047a004

Reference yield:

(2,4,6-trimethylbenzenesulfonyl)carbamic acid tert-butyl ester (56830-76-3) → N1,N5,N10,N14-tetrakis(mesitylenesulfonyl)-N1-(tert-butyl)-N14-ethylhomospermine (161452-22-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaI, NaH / 1.) DMF, 25 min, 2.) DMF, 70 deg C, 1 d

2: 100 percent / H₂, conc. NH₄OH / Raney Ni / methanol / 6 h / 50 - 55 Torr

3: 87 percent / 1N aq. NaOH / CH₂Cl₂ / 24 h / 0 - 20 °C

4: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, a) 0 deg C, 15 min, b) 70 deg C, overnight

5: 97 percent / TFA / CH₂Cl₂ / 0.83 h / 0 - 20 °C

6: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 70-80 deg C, 8 h

With ammonium hydroxide; sodium hydroxide; hydrogen; sodium hydride; trifluoroacetic acid; sodium iodide; nickel; In methanol; dichloromethane;

DOI:10.1021/jm00047a004

Reference yield:

2,4,6-trimethylbenzenesulfonamide (4543-58-2) → N1,N5,N10,N14-tetrakis(mesitylenesulfonyl)-N1-(tert-butyl)-N14-ethylhomospermine (161452-22-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 24 h / Heating

2: various solvent(s) / 1 h / 170 °C

3: various solvent(s) / 8 h / Ambient temperature

4: 1.) NaI, NaH / 1.) DMF, 25 min, 2.) DMF, 70 deg C, 1 d

5: 100 percent / H₂, conc. NH₄OH / Raney Ni / methanol / 6 h / 50 - 55 Torr

6: 87 percent / 1N aq. NaOH / CH₂Cl₂ / 24 h / 0 - 20 °C

7: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, a) 0 deg C, 15 min, b) 70 deg C, overnight

8: 97 percent / TFA / CH₂Cl₂ / 0.83 h / 0 - 20 °C

9: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, 70-80 deg C, 8 h

With ammonium hydroxide; sodium hydroxide; hydrogen; sodium hydride; trifluoroacetic acid; sodium iodide; nickel; In methanol; dichloromethane;

DOI:10.1021/jm00047a004

upstream raw materials:

N-(tert-butyl)-N-(4-bromobutyl)mesitylenesulfonamide

1,6,11-tris(mesitylenesulfonyl)-1,6,11-triazatridecane

2-mesitylenesulphonyl chloride

2,4,6-trimethylbenzenesulfonamide

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