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

Base Information

• Chemical Name: 2-{(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}-2-(cyclohexylmethyl)propane-1,3-diol
• CAS No.: 944163-71-7
• Molecular Formula: C₂₀H₄₀O₃Si
• Molecular Weight: 356.621
• Mol file: 944163-71-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

acetic acid 4-(tert-butyldimethylsilanyloxy)but-2-enyl ester (143158-97-8) → 2-{(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}-2-(cyclohexylmethyl)propane-1,3-diol (944163-71-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dppb; NaH / Pd₂(dba)3 / tetrahydrofuran / 20 °C

1.2: 77 percent / tetrahydrofuran / 24 h / 20 °C

2.1: 75 percent / LiAlH₄ / diethyl ether / 0.5 h / 20 °C

With lithium aluminium tetrahydride; sodium hydride; 1,4-di(diphenylphosphino)-butane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; diethyl ether;

DOI:10.1002/ejoc.200601019

Reference yield:

2-cyclohexylmethyl-malonic acid dimethyl ester (217654-79-0) → 2-{(E)-4-[(tert-butyldimethylsilyl)oxy]but-2-en-1-yl}-2-(cyclohexylmethyl)propane-1,3-diol (944163-71-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dppb; NaH / Pd₂(dba)3 / tetrahydrofuran / 20 °C

1.2: 77 percent / tetrahydrofuran / 24 h / 20 °C

2.1: 75 percent / LiAlH₄ / diethyl ether / 0.5 h / 20 °C

With lithium aluminium tetrahydride; sodium hydride; 1,4-di(diphenylphosphino)-butane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; diethyl ether;

DOI:10.1002/ejoc.200601019

upstream raw materials:

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

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

2-cyclohexylmethyl-malonic acid dimethyl ester

Downstream raw materials:

(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