(Z)-N-(4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-4-methyl-N-(3-phen-ylprop-2-yn-1-yl)benzenesulfonamide

Base Information

• Chemical Name: (Z)-N-(4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-4-methyl-N-(3-phen-ylprop-2-yn-1-yl)benzenesulfonamide
• CAS No.: 1372714-60-7
• Molecular Formula: C₂₆H₃₅NO₃SSi
• Molecular Weight: 469.72
• Mol file: 1372714-60-7.mol

Synonyms:(Z)-N-(4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-4-methyl-N-(3-phen-ylprop-2-yn-1-yl)benzenesulfonamide

Chemical Property of (Z)-N-(4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-4-methyl-N-(3-phen-ylprop-2-yn-1-yl)benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-N-(4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-4-methyl-N-(3-phen-ylprop-2-yn-1-yl)benzenesulfonamide

There total 2 articles about (Z)-N-(4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-4-methyl-N-(3-phen-ylprop-2-yn-1-yl)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:

tert-butyldimethylsilyl chloride (18162-48-6) → (Z)-N-(4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-4-methyl-N-(3-phen-ylprop-2-yn-1-yl)benzenesulfonamide (1372714-60-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 30 °C

2.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2.2: 2.5 h / 0 - 20 °C / Inert atmosphere

3.1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / 0.33 h / 20 °C / Inert atmosphere

3.2: 6 h / 20 °C / Inert atmosphere

With dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/jccs.201400121

Reference yield:

(Z)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol (91202-69-6,134297-05-5,113123-37-8) → (Z)-N-(4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-4-methyl-N-(3-phen-ylprop-2-yn-1-yl)benzenesulfonamide (1372714-60-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 2.5 h / 0 - 20 °C / Inert atmosphere

2.1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / 0.33 h / 20 °C / Inert atmosphere

2.2: 6 h / 20 °C / Inert atmosphere

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine; In tetrahydrofuran;

DOI:10.1002/jccs.201400121

Reference yield: 50.0%

(Z)-N-(4-((tert-butyldimethylsilyl)oxy)but-2-en-1-yl)-4-methyl-N-(3-phen-ylprop-2-yn-1-yl)benzenesulfonamide (1372714-60-7) → 7-(((tert-butyl)dimethylsilyloxy)methyl)-6-phenyl-3-tosyl-3-azabicyclo[4.1.0]hept-4-ene (1372714-61-8)

Guidance literature:

With platinum(IV) chloride; In 1,4-dioxane; at 25 ℃; for 1h;

DOI:10.1055/s-0031-1290314

upstream raw materials:

tert-butyldimethylsilyl chloride

(Z)-4-(tert-butyldimethylsilyloxy)but-2-en-1-ol

Downstream raw materials:

C₂₀H₂₁NO₃S

7-(((tert-butyl)dimethylsilyloxy)methyl)-6-phenyl-3-tosyl-3-azabicyclo[4.1.0]hept-4-ene

(6-phenyl-3-tosyl-3-azabicyclo[4.1.0]hept-4-en-7-yl)methanol