(E)-5-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one

Base Information

Chemical Name:(E)-5-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one
CAS No.:1610729-78-6
Molecular Formula:C₃₅H₅₁NO₅Si
Molecular Weight:593.879
Hs Code.:

Synonyms:(E)-5-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one

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Chemical Property of (E)-5-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one

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Technology Process of (E)-5-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one

There total 17 articles about (E)-5-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one 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: 87.0%

: 1610729-77-5
(E)-4-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-2-(chloromethyl)-5-methoxy-3-(methoxymethoxy)-N-phenethylbenzamide

: 1610729-78-6
(E)-5-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.416667h;
DOI:10.1021/jo500795z

Reference yield: 68.0%

: 5-bromo-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one

: (E)-tert-butyl((2,6-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octa-2,6-dien-4-yl)oxy)dimethylsilane

: 1610729-78-6
(E)-5-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one

Guidance literature:: With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate; In N,N-dimethyl-formamide; at 110 ℃; for 2h; Inert atmosphere; Microwave irradiation;
DOI:10.1021/acs.joc.7b00920

Reference yield:

: 1610729-67-3
(E)-5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-ol

: 1610729-78-6
(E)-5-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-6-methoxy-4-(methoxymethoxy)-2-phenethylisoindolin-1-one

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-butyllithium / tetrahydrofuran / 0.58 h / -78 °C

1.2: 0.58 h / -78 °C

2.1: tetrahydrofuran / 5.5 h / -78 - -40 °C

3.1: trans-bis(triphenylphosphine)palladium dichloride; cesium fluoride / N,N-dimethyl-formamide / 24 h / 85 °C

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.08 h / 0 °C

5.1: silver carbonate / toluene / 3 h / Reflux

6.1: boric acid; water / 114 h / 20 °C

7.1: triethylamine; methanesulfonyl chloride / dichloromethane / 0.83 h / 0 °C

8.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.42 h / 0 °C

With lithium aluminium tetrahydride; n-butyllithium; trans-bis(triphenylphosphine)palladium dichloride; water; boric acid; sodium hydride; methanesulfonyl chloride; triethylamine; cesium fluoride; silver carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 3.1: |Stille Cross Coupling;
DOI:10.1021/jo500795z