(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (E)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl ester

Base Information

Chemical Name:(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (E)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl ester
CAS No.:498548-59-7
Molecular Formula:C₃₄H₅₂O₃Si
Molecular Weight:536.871
Hs Code.:

Synonyms:(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (E)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl ester

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Chemical Property of (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (E)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl ester

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Technology Process of (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (E)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl ester

There total 4 articles about (5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (E)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl ester 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:

: 57303-04-5
arachidonoyl chloride

: 498548-56-4
2-(4-((tert-butyldimethylsilyl)-oxy)phenyl)acetaldehyde

: 498548-59-7
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (E)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl ester

Guidance literature:: 2-(4-((tert-butyldimethylsilyl)-oxy)phenyl)acetaldehyde; With potassium hexamethylsilazane; In tetrahydrofuran; monoethylene glycol diethyl ether; at -5 ℃; for 0.0166667h;

arachidonoyl chloride; In tetrahydrofuran; monoethylene glycol diethyl ether; at 20 ℃; for 0.25h; Further stages.;
DOI:10.1021/ol0267681

Reference yield:

: 96013-68-2
tert-butyl(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenoxy)dimethylsilane

: 498548-59-7
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (E)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: I₂ / methanol / 4 h

2.1: 67 percent / (COCl)2; DMSO / CH₂Cl₂ / -50 °C

3.1: potassium bis(trimethylsilyl)amide / 1,2-diethoxy-ethane; tetrahydrofuran / 0.02 h / -5 °C

3.2: 1,2-diethoxy-ethane; tetrahydrofuran / 0.25 h / 20 °C

With oxalyl dichloride; iodine; potassium hexamethylsilazane; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; monoethylene glycol diethyl ether; 2.1: Swern oxidation;
DOI:10.1021/ol0267681

Reference yield:

: 96013-75-1
2-(4{[tert-butyl(dimethyl)silyl]oxy}phenyl)ethanol

: 498548-59-7
(5Z,8Z,11Z,14Z)-Icosa-5,8,11,14-tetraenoic acid (E)-2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 67 percent / (COCl)2; DMSO / CH₂Cl₂ / -50 °C

2.1: potassium bis(trimethylsilyl)amide / 1,2-diethoxy-ethane; tetrahydrofuran / 0.02 h / -5 °C

2.2: 1,2-diethoxy-ethane; tetrahydrofuran / 0.25 h / 20 °C

With oxalyl dichloride; potassium hexamethylsilazane; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; monoethylene glycol diethyl ether; 1.1: Swern oxidation;
DOI:10.1021/ol0267681