tert-butyl-[5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyloxy]-dimethyl-silane

Base Information

• Chemical Name: tert-butyl-[5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyloxy]-dimethyl-silane
• CAS No.: 926290-18-8
• Molecular Formula: C₂₃H₄₀O₃Si
• Molecular Weight: 392.654
• Mol file: 926290-18-8.mol

Synonyms:tert-butyl-[5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyloxy]-dimethyl-silane

Chemical Property of tert-butyl-[5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyloxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl-[5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyloxy]-dimethyl-silane

There total 3 articles about tert-butyl-[5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyloxy]-dimethyl-silane 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: 82.0%

7-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-1-en-3-ol (926290-08-6) + p-methoxybenzyl chloride (824-94-2) → tert-butyl-[5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyloxy]-dimethyl-silane (926290-18-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;

DOI:10.1021/ja067083p

Reference yield:

(2S,4R)-1-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal (147782-81-8) → tert-butyl-[5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyloxy]-dimethyl-silane (926290-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 627 mg / tetrahydrofuran / 0.17 h / -78 °C

2: 82 percent / NaH; tetra-n-butylammonium iodide / dimethylformamide / 2 h / 0 - 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja067083p

Reference yield:

(2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol (147782-80-7) → tert-butyl-[5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyloxy]-dimethyl-silane (926290-18-8)

Guidance literature:

Multi-step reaction with 3 steps

1: SO₃*pyridine; i-Pr₂NEt / CH₂Cl₂; dimethylsulfoxide / 0.33 h / 0 °C

2: 627 mg / tetrahydrofuran / 0.17 h / -78 °C

3: 82 percent / NaH; tetra-n-butylammonium iodide / dimethylformamide / 2 h / 0 - 20 °C

With pyridine-SO₃ complex; tetra-(n-butyl)ammonium iodide; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Parikh-Doering oxidation;

DOI:10.1021/ja067083p

upstream raw materials:

7-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-hept-1-en-3-ol

p-methoxybenzyl chloride

(2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol

(2S,4R)-1-<(tert-Butyldimethylsilyl)oxy>-2,4-dimethylpentanal

Downstream raw materials:

4-[1-hydroxy-5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enyl]-11-methyl-8-triethylsilanyloxy-9-vinyl-2,6-dioxa-tricyclo[5.2.2.0^1,5]undec-4-en-3-one

5-(4-methoxy-benzyloxy)-2,4-dimethyl-hept-6-enal