(E)-5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-en-1-ol

Base Information

• Chemical Name: (E)-5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-en-1-ol
• CAS No.: 1332864-58-0
• Molecular Formula: C₂₂H₃₀O₂Si
• Molecular Weight: 354.565
• Mol file: 1332864-58-0.mol

Synonyms:(E)-5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-en-1-ol

Chemical Property of (E)-5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-en-1-ol

There total 3 articles about (E)-5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-en-1-ol 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: 83.0%

(E)-ethyl 5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-enoate (1332864-57-9) → (E)-5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-en-1-ol (1332864-58-0)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/ja2066219

Reference yield:

C22H28OSi (1093394-96-7) → (E)-5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-en-1-ol (1332864-58-0) + C22H30O2Si

Guidance literature:

C₂₂H₂₈OSi; With bis-(1,2-dimethylpropyl)borane; In tetrahydrofuran; at 0 ℃; for 0.0833333h; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 1h; Overall yield = 92 %; Overall yield = 49 mg; diastereoselective reaction; Inert atmosphere;

DOI:10.1002/asia.201800134

Reference yield:

(E)-(tert-butyl)(4-iodo-3-methylbut-3-enyloxy)diphenylsilane (148583-99-7) → (E)-5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-en-1-ol (1332864-58-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: zirconocene dichloride; n-butyllithium / diethyl ether; hexane / 0.33 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

With n-butyllithium; zirconocene dichloride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/ja2066219

upstream raw materials:

(E)-ethyl 5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-enoate

(E)-(tert-butyl)(4-iodo-3-methylbut-3-enyloxy)diphenylsilane

C₂₂H₂₈OSi

Downstream raw materials:

(E)-(tert-butyl) 1-(5-((tert-butyl)diphenylsilyloxy)-3-methylpent-2-enyl)hydrazinecarboxylate

(E)-(tert-butyl) 2-((5-(tert-butyl)diphenylsilyloxy)-3-methylpent-1-en-3-yl)diazenecarboxylate

C₃₅H₃₈Cl₄N₂O₅Si