(4E,6S,8E,10E,12E,14E,16E,18R,19S)-methyl 6,18-bis((tert-butyldimethylsilyl)oxy)-20-((4-methoxybenzyl)oxy)-19-methylicosa-4,8,10,12,14,16-hexaenoate

Base Information

Chemical Name:(4E,6S,8E,10E,12E,14E,16E,18R,19S)-methyl 6,18-bis((tert-butyldimethylsilyl)oxy)-20-((4-methoxybenzyl)oxy)-19-methylicosa-4,8,10,12,14,16-hexaenoate
CAS No.:1393364-37-8
Molecular Formula:C₄₂H₆₈O₆Si₂
Molecular Weight:725.169
Hs Code.:

(4E,6S,8E,10E,12E,14E,16E,18R,19S)-methyl 6,18-bis((tert-butyldimethylsilyl)oxy)-20-((4-methoxybenzyl)oxy)-19-methylicosa-4,8,10,12,14,16-hexaenoate

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Chemical Property of (4E,6S,8E,10E,12E,14E,16E,18R,19S)-methyl 6,18-bis((tert-butyldimethylsilyl)oxy)-20-((4-methoxybenzyl)oxy)-19-methylicosa-4,8,10,12,14,16-hexaenoate

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Technology Process of (4E,6S,8E,10E,12E,14E,16E,18R,19S)-methyl 6,18-bis((tert-butyldimethylsilyl)oxy)-20-((4-methoxybenzyl)oxy)-19-methylicosa-4,8,10,12,14,16-hexaenoate

There total 9 articles about (4E,6S,8E,10E,12E,14E,16E,18R,19S)-methyl 6,18-bis((tert-butyldimethylsilyl)oxy)-20-((4-methoxybenzyl)oxy)-19-methylicosa-4,8,10,12,14,16-hexaenoate 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: 77.0%

: 1393364-33-4
tert-butyl(((3S,4S)-5-((4-methoxybenzyl)oxy)-4-methylpent-1-yn-3-yl)oxy)dimethylsilane

: 1393364-35-6
(S,4E,8E,10E,12E,14E)-methyl 6-(tert-butyldimethylsilyloxy)-15-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentadeca-4,8,10,12,14-pentaenoate

: 1393364-37-8
(4E,6S,8E,10E,12E,14E,16E,18R,19S)-methyl 6,18-bis((tert-butyldimethylsilyl)oxy)-20-((4-methoxybenzyl)oxy)-19-methylicosa-4,8,10,12,14,16-hexaenoate

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); barium hydroxide octahydrate; In N,N-dimethyl-formamide; for 4h; Inert atmosphere; Darkness;
DOI:10.1039/c2cc34052f

Reference yield:

: 1393364-32-3
(3S,4S)-5-(4-methoxybenzyloxy)-4-methyl-1-(trimethylsilyl)pent-1-yn-3-ol

: 1393364-37-8
(4E,6S,8E,10E,12E,14E,16E,18R,19S)-methyl 6,18-bis((tert-butyldimethylsilyl)oxy)-20-((4-methoxybenzyl)oxy)-19-methylicosa-4,8,10,12,14,16-hexaenoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

3.1: zirconocene dichloride; diisobutylaluminium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: dichloro bis(acetonitrile) palladium(II); barium hydroxide octahydrate / N,N-dimethyl-formamide / 4 h / Inert atmosphere; Darkness

With 2,6-dimethylpyridine; dichloro bis(acetonitrile) palladium(II); zirconocene dichloride; barium hydroxide octahydrate; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Suzuki-Miyaura coupling;
DOI:10.1039/c2cc34052f

Reference yield:

: 1393364-39-0
tert-butyl(((3S,4S)-5-((4-methoxybenzyl)oxy)-4-methyl-1-(trimethylsilyl)pent-1-yn-3-yl)oxy)dimethylsilane

: 1393364-37-8
(4E,6S,8E,10E,12E,14E,16E,18R,19S)-methyl 6,18-bis((tert-butyldimethylsilyl)oxy)-20-((4-methoxybenzyl)oxy)-19-methylicosa-4,8,10,12,14,16-hexaenoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

2.1: zirconocene dichloride; diisobutylaluminium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: dichloro bis(acetonitrile) palladium(II); barium hydroxide octahydrate / N,N-dimethyl-formamide / 4 h / Inert atmosphere; Darkness

With dichloro bis(acetonitrile) palladium(II); zirconocene dichloride; barium hydroxide octahydrate; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 3.1: Suzuki-Miyaura coupling;
DOI:10.1039/c2cc34052f