(Z)-(tert-butyldimethylsilanyloxy)-4,5-dimethyl-6-(para-methoxybenzyloxy)-hex-4-ene

Base Information

• Chemical Name: (Z)-(tert-butyldimethylsilanyloxy)-4,5-dimethyl-6-(para-methoxybenzyloxy)-hex-4-ene
• CAS No.: 1283712-84-4
• Molecular Formula: C₂₂H₃₈O₃Si
• Molecular Weight: 378.627
• Mol file: 1283712-84-4.mol

Synonyms:(Z)-(tert-butyldimethylsilanyloxy)-4,5-dimethyl-6-(para-methoxybenzyloxy)-hex-4-ene

Chemical Property of (Z)-(tert-butyldimethylsilanyloxy)-4,5-dimethyl-6-(para-methoxybenzyloxy)-hex-4-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(tert-butyldimethylsilanyloxy)-4,5-dimethyl-6-(para-methoxybenzyloxy)-hex-4-ene

There total 10 articles about (Z)-(tert-butyldimethylsilanyloxy)-4,5-dimethyl-6-(para-methoxybenzyloxy)-hex-4-ene 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: 76.0%

(E)-(tert-butyldimethylsilanyloxy)-4-methyl-5-iodo-6-(para-methoxybenzyloxy)-hex-4-ene (1283712-83-3) + dimethyl zinc(II) (544-97-8) → (Z)-(tert-butyldimethylsilanyloxy)-4,5-dimethyl-6-(para-methoxybenzyloxy)-hex-4-ene (1283712-84-4)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; toluene; at 25 - 110 ℃; for 2.08333h; Inert atmosphere;

DOI:10.1039/c1ob05448a

Reference yield: 76.0%

C21H35IO3Si + dimethyl zinc(II) (544-97-8) → (Z)-(tert-butyldimethylsilanyloxy)-4,5-dimethyl-6-(para-methoxybenzyloxy)-hex-4-ene (1283712-84-4)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In 1,4-dioxane; at 80 ℃;

DOI:10.1016/j.tetlet.2011.01.093

Reference yield:

methyl 6–(tert–butyldimethylsilyloxy)hex–2–ynoate (145383-97-7) → (Z)-(tert-butyldimethylsilanyloxy)-4,5-dimethyl-6-(para-methoxybenzyloxy)-hex-4-ene (1283712-84-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: copper(l) iodide / tetrahydrofuran / -45 °C

1.2: -45 - 0 °C

2.1: diisobutylaluminium hydride / dichloromethane / -78 °C

3.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 25 °C

4.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 80 °C

With copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; trifluorormethanesulfonic acid; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; cyclohexane; 4.1: Negishi cross-coupling reaction;

DOI:10.1016/j.tetlet.2011.01.093

upstream raw materials:

dimethyl zinc(II)

pent-1-yn-5-ol

5-[tert-butyldimethylsilyloxy]pent-1-yne

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2R,3S)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-8-(benzyloxy)-3-hydroxy-2,6,7-trimethyloct-6-en-1-one

(2R,3S)-1-((S)-4-benzyl-2-thioxooxazolidin-3-yl)-8-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2,6,7-trimethyloct-6-en-1-one

(2R,3S)-8-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-2,6,7-trimethyloct-6-enal

(4R,5S)-ethyl 10-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8,9-trimethyl-3-oxodec-8-enoate