(3R,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)octa-1,5-dien-3-yl acrylate

Base Information

Chemical Name:(3R,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)octa-1,5-dien-3-yl acrylate
CAS No.:1345017-63-1
Molecular Formula:C₃₂H₄₃NO₅Si
Molecular Weight:549.783
Hs Code.:

Synonyms:(3R,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)octa-1,5-dien-3-yl acrylate

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Chemical Property of (3R,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)octa-1,5-dien-3-yl acrylate

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Technology Process of (3R,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)octa-1,5-dien-3-yl acrylate

There total 5 articles about (3R,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)octa-1,5-dien-3-yl acrylate 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: 90.0%

: 1345017-50-6
tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxyocta-3,7-dien-2-ylcarbamate

: 814-68-6,25189-84-8
acryloyl chloride

: 1345017-63-1
(3R,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)octa-1,5-dien-3-yl acrylate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;
DOI:10.1016/j.tetlet.2011.08.084

Reference yield:

: 1345017-48-2
tert-butyl (2S,3R)-3-(allyloxy)-1-hydroxypent-4-en-2-ylcarbamate

: 1345017-63-1
(3R,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)octa-1,5-dien-3-yl acrylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 2.1: Wittig rearrangement;
DOI:10.1016/j.tetlet.2011.08.084

Reference yield:

: 1345017-47-1
(S)-tert-butyl 4-((R)-1-(allyloxy)allyl)-2,2-dimethyloxazolidine-3-carboxylate

: 1345017-63-1
(3R,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)octa-1,5-dien-3-yl acrylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: acetic acid / methanol; water / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; acetic acid; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 3.1: Wittig rearrangement;
DOI:10.1016/j.tetlet.2011.08.084