(1Z,3E)-1-(benzyldimethylsilyl)-3-methyl-5-(tetrahydropyran-2-yloxy)penta-1,3-diene

Base Information

• Chemical Name: (1Z,3E)-1-(benzyldimethylsilyl)-3-methyl-5-(tetrahydropyran-2-yloxy)penta-1,3-diene
• CAS No.: 1096538-13-4
• Molecular Formula: C₂₀H₃₀O₂Si
• Molecular Weight: 330.543
• Mol file: 1096538-13-4.mol

Synonyms:(1Z,3E)-1-(benzyldimethylsilyl)-3-methyl-5-(tetrahydropyran-2-yloxy)penta-1,3-diene

Chemical Property of (1Z,3E)-1-(benzyldimethylsilyl)-3-methyl-5-(tetrahydropyran-2-yloxy)penta-1,3-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1Z,3E)-1-(benzyldimethylsilyl)-3-methyl-5-(tetrahydropyran-2-yloxy)penta-1,3-diene

There total 2 articles about (1Z,3E)-1-(benzyldimethylsilyl)-3-methyl-5-(tetrahydropyran-2-yloxy)penta-1,3-diene 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)-1-benzyldimethylsilyl-3-methyl-5-(tetrahydropyran-2-yloxy)pent-3-en-1-yne (1096538-11-2) → (1Z,3E)-1-(benzyldimethylsilyl)-3-methyl-5-(tetrahydropyran-2-yloxy)penta-1,3-diene (1096538-13-4)

Guidance literature:

(E)-1-benzyldimethylsilyl-3-methyl-5-(tetrahydropyran-2-yloxy)pent-3-en-1-yne; With Schwartz's reagent; In tetrahydrofuran;

With pentane;

DOI:10.1021/ol802551a

Reference yield:

(E)-tetrahydro-2-<(3-methyl-2-penten-4-ynyl)oxy>-2H-pyran (41967-81-1,58389-95-0,61568-79-4,134079-53-1) + benzyl(chloro)dimethylsilane (1833-31-4) → (1Z,3E)-1-(benzyldimethylsilyl)-3-methyl-5-(tetrahydropyran-2-yloxy)penta-1,3-diene (1096538-13-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / hexanes; diethyl ether / 1.17 h / -78 °C / Inert atmosphere

1.2: 4 h / -78 - 20 °C / Inert atmosphere

2.1: Schwartz's reagent / tetrahydrofuran / 4 h / Inert atmosphere

2.2: 0.33 h / Inert atmosphere

With Schwartz's reagent; n-butyllithium; In tetrahydrofuran; hexanes; diethyl ether;

DOI:10.1002/chem.201103360

Reference yield: 78.0%

(1Z,3E)-1-(benzyldimethylsilyl)-3-methyl-5-(tetrahydropyran-2-yloxy)penta-1,3-diene (1096538-13-4) + C14H21I → 11-cis-tetrahydropyran-2-yl retinyl ether (1096538-06-5)

Guidance literature:

(1Z,3E)-1-(benzyldimethylsilyl)-3-methyl-5-(tetrahydropyran-2-yloxy)penta-1,3-diene; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere; Darkness;

C₁₄H₂₁I; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; at 20 ℃; for 1h; stereospecific reaction; Inert atmosphere; Darkness;

DOI:10.1002/chem.201103360

upstream raw materials:

(E)-1-benzyldimethylsilyl-3-methyl-5-(tetrahydropyran-2-yloxy)pent-3-en-1-yne

(E)-tetrahydro-2-<(3-methyl-2-penten-4-ynyl)oxy>-2H-pyran

benzyl(chloro)dimethylsilane

Downstream raw materials:

11-cis-tetrahydropyran-2-yl retinyl ether

(11Z)-retinal

11-cis-retinol

11-cis-9-demethyl-tetrahydropyran-2-yl retinyl ether