(4R,18R,E)-ethyl 18-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)nonadec-2-enoate

Base Information

Chemical Name:(4R,18R,E)-ethyl 18-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)nonadec-2-enoate
CAS No.:1587697-45-7
Molecular Formula:C₃₅H₆₂O₅Si
Molecular Weight:590.96
Hs Code.:

Synonyms:(4R,18R,E)-ethyl 18-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)nonadec-2-enoate

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Chemical Property of (4R,18R,E)-ethyl 18-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)nonadec-2-enoate

Chemical Property:

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Technology Process of (4R,18R,E)-ethyl 18-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)nonadec-2-enoate

There total 15 articles about (4R,18R,E)-ethyl 18-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)nonadec-2-enoate 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:

: C₃₁H₅₆O₄Si

: 124755-24-4
ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate

: 1587697-44-6
(4R,18R,Z)-ethyl 18-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)nonadec-2-enoate

: 1587697-45-7
(4R,18R,E)-ethyl 18-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)nonadec-2-enoate

Guidance literature:: ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at 0 ℃; for 0.25h;

C₃₁H₅₆O₄Si; In tetrahydrofuran; at -78 ℃; for 2h;
DOI:10.1002/ejoc.201301287

Reference yield:

: (R)-tert-butyl(heptadec-16-en-2-yloxy)dimethylsilane

: 1587697-45-7
(4R,18R,E)-ethyl 18-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)nonadec-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium hexacyanoferrate(III); potassium carbonate; methanesulfonamide; (DHQD)2AQN; potassium osmate(VI) dihydrate; water / tert-butyl alcohol / 24 h / 0 °C

2.1: toluene-4-sulfonic acid / benzene / 12 h / 20 °C

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 5 h / -78 °C / Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

5.1: potassium hexamethylsilazane; 18-crown-6 ether / tetrahydrofuran / 0.25 h / 0 °C

5.2: 2 h / -78 °C

With potassium osmate(VI) dihydrate; 18-crown-6 ether; methanesulfonamide; (DHQD)2AQN; water; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; toluene; tert-butyl alcohol; benzene; 1.1: |Sharpless Dihydroxylation / 5.2: |Still-Gennary Z-Olefination;
DOI:10.1002/ejoc.201301287

Reference yield:

: 1587697-43-5
(2R,16R)-16-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)heptadecan-1-ol

: 1587697-45-7
(4R,18R,E)-ethyl 18-(tert-butyldimethylsilyloxy)-4-(4-methoxybenzyloxy)nonadec-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

2.1: potassium hexamethylsilazane; 18-crown-6 ether / tetrahydrofuran / 0.25 h / 0 °C

2.2: 2 h / -78 °C

With 18-crown-6 ether; potassium hexamethylsilazane; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 2.2: |Still-Gennary Z-Olefination;
DOI:10.1002/ejoc.201301287