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

Base Information

Chemical Name:(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid allyl ester
CAS No.:329184-72-7
Molecular Formula:C₄₀H₅₉NO₅Si
Molecular Weight:661.998
Hs Code.:

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

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

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

There total 9 articles about (S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid allyl 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: 76.0%

: 107-18-6
allyl alcohol

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

: 329184-72-7
(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid allyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 18h;
DOI:10.1021/jo001200w

Reference yield:

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

: 329184-72-7
(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid allyl ester

Guidance literature:: Multi-step reaction with 9 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

9: 76 percent / DMAP; DCC / CH₂Cl₂ / 18 h / 20 °C

With dmap; lithium hydroxide; sodium hydrogen sulfate; copper(l) iodide; n-butyllithium; naphthalene; hydrogen; bromine; sodium; sodium hydride; dicyclohexyl-carbodiimide; 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

: 329184-72-7
(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienoic acid allyl ester

Guidance literature:: Multi-step reaction with 8 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

8: 76 percent / DMAP; DCC / CH₂Cl₂ / 18 h / 20 °C

With dmap; lithium hydroxide; sodium hydrogen sulfate; copper(l) iodide; n-butyllithium; naphthalene; hydrogen; bromine; sodium; sodium hydride; dicyclohexyl-carbodiimide; 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