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

Base Information

Chemical Name:(E)-4-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-2-(chloromethyl)-5-methoxy-3-(methoxymethoxy)-N-phenethylbenzamide
CAS No.:1610729-77-5
Molecular Formula:C₃₅H₅₂ClNO₅Si
Molecular Weight:630.34
Hs Code.:

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

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

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

There total 10 articles about (E)-4-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-2-(chloromethyl)-5-methoxy-3-(methoxymethoxy)-N-phenethylbenzamide 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: 76.0%

: 1610729-76-4
(E)-4-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-2-(hydroxymethyl)-5-methoxy-3-(methoxymethoxy)-N-phenethylbenzamide

: 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

Guidance literature:: With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 0.833333h;
DOI:10.1021/jo500795z

Reference yield:

: 1610729-68-4
(E)-6-(5-((tert-butyldimethylsilyl)oxy)-3,7-dimethylocta-2,6-dien-1-yl)-5-methoxy-7-(methoxymethoxy)isobenzofuran-1(3H)-one

: 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

Guidance literature:: Multi-step reaction with 4 steps

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

2: silver carbonate / toluene / 3 h / Reflux

3: boric acid; water / 114 h / 20 °C

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

With lithium aluminium tetrahydride; water; boric acid; methanesulfonyl chloride; triethylamine; silver carbonate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/jo500795z

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

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