(R)-4-(4'-methoxybenzyloxy)-3-methyl-2-(trimethylsilylmethyl)-1-butene

Base Information

• Chemical Name: (R)-4-(4'-methoxybenzyloxy)-3-methyl-2-(trimethylsilylmethyl)-1-butene
• CAS No.: 267236-35-1
• Molecular Formula: C₁₇H₂₈O₂Si
• Molecular Weight: 292.494
• Mol file: 267236-35-1.mol

Synonyms:(R)-4-(4'-methoxybenzyloxy)-3-methyl-2-(trimethylsilylmethyl)-1-butene

Chemical Property of (R)-4-(4'-methoxybenzyloxy)-3-methyl-2-(trimethylsilylmethyl)-1-butene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(4'-methoxybenzyloxy)-3-methyl-2-(trimethylsilylmethyl)-1-butene

There total 2 articles about (R)-4-(4'-methoxybenzyloxy)-3-methyl-2-(trimethylsilylmethyl)-1-butene 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: 70.0%

(trimethylsilyl)methylmagnesium chloride (13170-43-9) + methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate (132969-71-2) → (R)-4-(4'-methoxybenzyloxy)-3-methyl-2-(trimethylsilylmethyl)-1-butene (267236-35-1)

Guidance literature:

(trimethylsilyl)methylmagnesium chloride; With cerium(III) chloride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h;

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate; In tetrahydrofuran; diethyl ether; at 20 ℃; for 4h; Further stages.;

DOI:10.1021/ol0000197

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → (R)-4-(4'-methoxybenzyloxy)-3-methyl-2-(trimethylsilylmethyl)-1-butene (267236-35-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 20 °C

2.1: cerium chloride / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

2.2: 70 percent / tetrahydrofuran; diethyl ether / 4 h / 20 °C

With cerium(III) chloride; camphor-10-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Etherification / 2.1: Addition / 2.2: Addition;

DOI:10.1021/ol0000197

Reference yield: 51.0%

(2R,3S)-5-bromo-2,3-epoxy-hex-5-enal (267236-34-0) + (R)-4-(4'-methoxybenzyloxy)-3-methyl-2-(trimethylsilylmethyl)-1-butene (267236-35-1) → (2R,5R,6S,7S)-9-bromo-6,7-epoxy-1-(4-methoxybenzyloxy)-2-methyl-3-methylene-dec-9-en-5-ol + (2R,5S,6S,7S)-9-bromo-6,7-epoxy-1-(4-methoxybenzyloxy)-2-methyl-3-methylene-dec-9-en-5-ol

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1021/jo4002382

upstream raw materials:

(trimethylsilyl)methylmagnesium chloride

methyl (2S)-[(4-methoxybenzyl)oxy]-2-methylpropanoate

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

(2R,5S,6S,7S)-6,7-epoxy-1-(4-methoxybenzyloxy)-2-methyl-3-methylene-9-trimethylsilanyldec-9-en-5-ol

(2R,5R,6S,7S)-6,7-epoxy-1-(4-methoxybenzyloxy)-2-methyl-3-methylene-9-trimethylsilanyldec-9-en-5-ol