(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid

Base Information

Chemical Name:(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid
CAS No.:329184-70-5
Molecular Formula:C₃₇H₅₅NO₅Si
Molecular Weight:621.933
Hs Code.:

Synonyms:(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid

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Chemical Property of (S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid

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Technology Process of (S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid

There total 8 articles about (S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid 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: 82.0%

: 329184-69-2
[2-(tert-butyldiphenylsilanyloxy)ethyl]-[(S)-(3Z,6Z)-10-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-1-propyldeca-3,6-dienyl]carbamic acid dimethylethyl ester

: 329184-70-5
(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid

Guidance literature:: With lithium hydroxide; sodium hydrogen sulfate; In 1,2-dimethoxyethane; water; at 20 ℃; for 8h;
DOI:10.1021/jo001200w

Reference yield:

: 170956-17-9
(S)-1-[(4-methylphenyl)sulfonyl]-2-propylaziridin

: 329184-70-5
(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / n-BuLi / tetrahydrofuran; hexane / 24 h / 20 °C

2: 80 percent / NaH / dimethylformamide / 48 h / 0 - 40 °C

3: 77 percent / Ph₂PCH₂CH₂PPh₂; Br₂ / CH₂Cl₂ / 3.5 h / 0 - 20 °C

4: 83 percent / n-BuLi; CuI / tetrahydrofuran; hexane / 27 h / 35 °C

5: 8.5 mg / H₂ / Lindlar catalyst / ethyl acetate; ethanol / 1.5 h

6: 97 percent / Na; naphthalene / 1,2-dimethoxy-ethane / -75 - 20 °C

7: 96 percent / tetrahydrofuran / 17 h / 20 °C

8: 82 percent / NaHSO₄; LiOH / 1,2-dimethoxy-ethane; H₂O / 8 h / 20 °C

With lithium hydroxide; sodium hydrogen sulfate; copper(l) iodide; n-butyllithium; naphthalene; hydrogen; bromine; sodium; sodium hydride; 1,2-bis-(diphenylphosphino)ethane; Lindlar's catalyst; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo001200w

Reference yield:

: 329184-63-6
4-methyl-N-[(S)-1-propyl-5-(tetrahydropyran-2-yloxy)pent-3-ynyl]benzenesulfonamide

: 329184-70-5
(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / NaH / dimethylformamide / 48 h / 0 - 40 °C

2: 77 percent / Ph₂PCH₂CH₂PPh₂; Br₂ / CH₂Cl₂ / 3.5 h / 0 - 20 °C

3: 83 percent / n-BuLi; CuI / tetrahydrofuran; hexane / 27 h / 35 °C

4: 8.5 mg / H₂ / Lindlar catalyst / ethyl acetate; ethanol / 1.5 h

5: 97 percent / Na; naphthalene / 1,2-dimethoxy-ethane / -75 - 20 °C

6: 96 percent / tetrahydrofuran / 17 h / 20 °C

7: 82 percent / NaHSO₄; LiOH / 1,2-dimethoxy-ethane; H₂O / 8 h / 20 °C

With lithium hydroxide; sodium hydrogen sulfate; copper(l) iodide; n-butyllithium; naphthalene; hydrogen; bromine; sodium; sodium hydride; 1,2-bis-(diphenylphosphino)ethane; Lindlar's catalyst; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo001200w