N-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-methyl-N-((E)-penta-2,4-dienyl)-benzenesulfonamide

Base Information

• Chemical Name: N-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-methyl-N-((E)-penta-2,4-dienyl)-benzenesulfonamide
• CAS No.: 202975-03-9
• Molecular Formula: C₂₂H₃₇NO₃SSi
• Molecular Weight: 423.692
• Mol file: 202975-03-9.mol

Synonyms:N-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-methyl-N-((E)-penta-2,4-dienyl)-benzenesulfonamide

Chemical Property of N-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-methyl-N-((E)-penta-2,4-dienyl)-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-methyl-N-((E)-penta-2,4-dienyl)-benzenesulfonamide

There total 1 articles about N-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-methyl-N-((E)-penta-2,4-dienyl)-benzenesulfonamide 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%

(E)-5-bromopenta-1,3-diene (52022-82-9) + N-[4-(tert-butyldimethylsilyloxy)butyl]-tosylamide (192586-59-7) → N-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-methyl-N-((E)-penta-2,4-dienyl)-benzenesulfonamide (202975-03-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0040-4020(97)10215-0

Reference yield: 89.0%

N-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-methyl-N-((E)-penta-2,4-dienyl)-benzenesulfonamide (202975-03-9) → N-(4-Hydroxy-butyl)-4-methyl-N-((E)-penta-2,4-dienyl)-benzenesulfonamide (202975-08-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4020(97)10215-0

Reference yield:

N-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-4-methyl-N-((E)-penta-2,4-dienyl)-benzenesulfonamide (202975-03-9) → 4-aza-2-propyl-4-(p-toluenesulfonyl)cycloheptanone

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / TBAF / tetrahydrofuran / 0.25 h / 0 °C

2: 90 percent / Dess-Martin reagent / CH₂Cl₂ / 1 h / Ambient temperature

3: Ni(cod)2, PPh₃ / tetrahydrofuran / 18 h / Ambient temperature

4: TBAF / tetrahydrofuran

5: H₂ / Pd/C / methanol

6: Dess-Martin reagent

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4020(97)10215-0

upstream raw materials:

(E)-5-bromopenta-1,3-diene

N-[4-(tert-butyldimethylsilyloxy)butyl]-tosylamide

Downstream raw materials:

N-(4-Hydroxy-butyl)-4-methyl-N-((E)-penta-2,4-dienyl)-benzenesulfonamide

4-Methyl-N-(4-oxo-butyl)-N-((E)-penta-2,4-dienyl)-benzenesulfonamide

3-((E)-Propenyl)-1-(toluene-4-sulfonyl)-4-triethylsilanyloxy-azepane