dimethyl {(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}(cyclohexylmethyl)malonate

Base Information

• Chemical Name: dimethyl {(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}(cyclohexylmethyl)malonate
• CAS No.: 944163-58-0
• Molecular Formula: C₂₂H₄₀O₅Si
• Molecular Weight: 412.642
• Mol file: 944163-58-0.mol

Synonyms:dimethyl {(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}(cyclohexylmethyl)malonate

Chemical Property of dimethyl {(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}(cyclohexylmethyl)malonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl {(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}(cyclohexylmethyl)malonate

There total 1 articles about dimethyl {(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}(cyclohexylmethyl)malonate 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: 77.0%

acetic acid 4-(tert-butyldimethylsilanyloxy)but-2-enyl ester (143158-97-8) + 2-cyclohexylmethyl-malonic acid dimethyl ester (217654-79-0) → dimethyl {(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}(cyclohexylmethyl)malonate (944163-58-0)

Guidance literature:

2-cyclohexylmethyl-malonic acid dimethyl ester; With sodium hydride; 1,4-di(diphenylphosphino)-butane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; at 20 ℃;

acetic acid 4-(tert-butyldimethylsilanyloxy)but-2-enyl ester; In tetrahydrofuran; at 20 ℃; for 24h; Further stages.;

DOI:10.1002/ejoc.200601019

Reference yield: 75.0%

dimethyl {(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}(cyclohexylmethyl)malonate (944163-58-0) → 2-{(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}-2-(cyclohexylmethyl)propane-1,3-diol (944163-71-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 0.5h;

DOI:10.1002/ejoc.200601019

Reference yield:

dimethyl {(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}(cyclohexylmethyl)malonate (944163-58-0) → rac-(3R,5S)-3-cyclohexylmethyl-3-hydroxymethyl-5-vinyltetrahydrofuran

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / LiAlH₄ / diethyl ether / 0.5 h / 20 °C

2: 96 percent / Bu₄NF*3H₂O / tetrahydrofuran / 15 h / 20 °C

3: 56 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

4: dppb / Pd₂(dba)3 / tetrahydrofuran / 1 h / 25 °C

With pyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; 1,4-di(diphenylphosphino)-butane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/ejoc.200601019

upstream raw materials:

acetic acid 4-(tert-butyldimethylsilanyloxy)but-2-enyl ester

2-cyclohexylmethyl-malonic acid dimethyl ester

Downstream raw materials:

2-{(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}-2-(cyclohexylmethyl)propane-1,3-diol

(E)-5-(cyclohexylmethyl)-5-(hydroxymethyl)hex-2-ene-1,6-diol

(E)-5-(cyclohexylmethyl)-6-hydroxy-5-(hydroxymethyl)hex-2-en-1-yl methyl carbonate