(S)-((1-(benzyloxy)hex-5-en-3-yl)oxy)(tert-butyl)dimethylsilane

Base Information

• Chemical Name: (S)-((1-(benzyloxy)hex-5-en-3-yl)oxy)(tert-butyl)dimethylsilane
• CAS No.: 236427-78-4
• Molecular Formula: C₁₉H₃₂O₂Si
• Molecular Weight: 320.547
• Mol file: 236427-78-4.mol

Synonyms:(S)-((1-(benzyloxy)hex-5-en-3-yl)oxy)(tert-butyl)dimethylsilane

Chemical Property of (S)-((1-(benzyloxy)hex-5-en-3-yl)oxy)(tert-butyl)dimethylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-((1-(benzyloxy)hex-5-en-3-yl)oxy)(tert-butyl)dimethylsilane

There total 3 articles about (S)-((1-(benzyloxy)hex-5-en-3-yl)oxy)(tert-butyl)dimethylsilane 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: 96.0%

(S)-1-(benzyloxy)-3-hydroxyhex-5-ene (91285-62-0,111322-01-1,119239-98-4) + tert-butyldimethylsilyl chloride (18162-48-6) → (S)-((1-(benzyloxy)hex-5-en-3-yl)oxy)(tert-butyl)dimethylsilane (236427-78-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 16h;

DOI:10.1002/chem.201504675

Reference yield:

(2R)-2-(2-benzyloxyethyl)oxirane (115114-87-9) → (S)-((1-(benzyloxy)hex-5-en-3-yl)oxy)(tert-butyl)dimethylsilane (236427-78-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / CuI / tetrahydrofuran / -25 - 0 °C

2: imidazole / dimethylformamide / 20 °C

With 1H-imidazole; copper(l) iodide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja0618954

Reference yield:

3-Benzyloxypropanal (19790-60-4) → (S)-((1-(benzyloxy)hex-5-en-3-yl)oxy)(tert-butyl)dimethylsilane (236427-78-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (S)-[1,1']-binaphthalenyl-2,2'-diol; titanium(IV) isopropylate / dichloromethane / 0.08 h / Molecular sieve; Inert atmosphere; Reflux

1.2: 161 h / -78 - -20 °C / Molecular sieve; Inert atmosphere; Reflux

2.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/chem.201504675

upstream raw materials:

(S)-1-(benzyloxy)-3-hydroxyhex-5-ene

tert-butyldimethylsilyl chloride

(2R)-2-(2-benzyloxyethyl)oxirane

3-Benzyloxypropanal

Downstream raw materials:

(S)-5-(benzyloxy)-3-(tert-butyldimethylsilyloxy)pentan-1-ol

(R)-8-Benzyloxy-6-hydroxy-oct-1-en-4-one

(3R,5S)-1-(benzyloxy)oct-7-ene-3,5-diol

(4S,6S)-4-[2-(benzyloxy)ethyl]-2,2-dimethyl-6-(prop-2-en-1-yl)-1,3-dioxane