(3E,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-(4-methoxybenzyloxymethyl)hept-3-ene

Base Information

Chemical Name:(3E,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-(4-methoxybenzyloxymethyl)hept-3-ene
CAS No.:1170989-63-5
Molecular Formula:C₂₃H₄₀O₃Si
Molecular Weight:392.654
Hs Code.:

Synonyms:(3E,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-(4-methoxybenzyloxymethyl)hept-3-ene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3E,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-(4-methoxybenzyloxymethyl)hept-3-ene

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Technology Process of (3E,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-(4-methoxybenzyloxymethyl)hept-3-ene

There total 4 articles about (3E,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-(4-methoxybenzyloxymethyl)hept-3-ene 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: 94.0%

: 1170989-60-2
(2E,4S)-4-(tert-butyldimethylsilyloxymethyl)-2-ethylhex-2-en-1-ol

: 824-94-2
p-methoxybenzyl chloride

: 1170989-63-5
(3E,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-(4-methoxybenzyloxymethyl)hept-3-ene

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 21h;
DOI:10.1016/j.tetlet.2009.02.101

Reference yield:

: 1170989-57-7
ethyl (2E,4S)-4-(tert-butyldimethylsilyloxy)methyl-2-ethyl-hex-2-enoate

: 1170989-63-5
(3E,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-(4-methoxybenzyloxymethyl)hept-3-ene

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.67 h / -78 °C / Inert atmosphere

1.2: 3.5 h / -78 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

2.2: 21 h / 0 - 20 °C

With sodium hydride; diisobutylaluminium hydride; In dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1016/j.tet.2011.04.006

Reference yield:

: 111042-76-3
(-)-(2S)-2-((tert-Butyldimethylsiloxy)methyl)butan-1-ol

: 1170989-63-5
(3E,5S)-5-(tert-butyldimethylsilyloxymethyl)-3-(4-methoxybenzyloxymethyl)hept-3-ene

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - 20 °C / Inert atmosphere

2.1: toluene / 40 h / Reflux

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.67 h / -78 °C / Inert atmosphere

3.2: 3.5 h / -78 - 20 °C / Inert atmosphere

4.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C

4.2: 21 h / 0 - 20 °C

With oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; In dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Wittig reaction;
DOI:10.1016/j.tet.2011.04.006