(6S)-(2E,4Z,8E)-1-(benzenesulfanyl-ethyl)-10-(tert-butyldiphenylsilanyloxy)-4,6,8-trimethyldeca-2,4,8-trien-1-ol

Base Information

Chemical Name:(6S)-(2E,4Z,8E)-1-(benzenesulfanyl-ethyl)-10-(tert-butyldiphenylsilanyloxy)-4,6,8-trimethyldeca-2,4,8-trien-1-ol
CAS No.:343262-72-6
Molecular Formula:C₃₇H₄₈O₂SSi
Molecular Weight:584.938
Hs Code.:

Synonyms:(6S)-(2E,4Z,8E)-1-(benzenesulfanyl-ethyl)-10-(tert-butyldiphenylsilanyloxy)-4,6,8-trimethyldeca-2,4,8-trien-1-ol

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Chemical Property of (6S)-(2E,4Z,8E)-1-(benzenesulfanyl-ethyl)-10-(tert-butyldiphenylsilanyloxy)-4,6,8-trimethyldeca-2,4,8-trien-1-ol

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Technology Process of (6S)-(2E,4Z,8E)-1-(benzenesulfanyl-ethyl)-10-(tert-butyldiphenylsilanyloxy)-4,6,8-trimethyldeca-2,4,8-trien-1-ol

There total 7 articles about (6S)-(2E,4Z,8E)-1-(benzenesulfanyl-ethyl)-10-(tert-butyldiphenylsilanyloxy)-4,6,8-trimethyldeca-2,4,8-trien-1-ol 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: 92.0%

: 27098-65-3
3-phenylsulfanyl-propionaldehyde

: 343262-71-5
(3Z,7E)-(5S)-9-(tert-butyldiphenylsilanyloxy)-3,5,7-trimethylocta-3,7-dien-1-yne

: 343262-72-6
(6S)-(2E,4Z,8E)-1-(benzenesulfanyl-ethyl)-10-(tert-butyldiphenylsilanyloxy)-4,6,8-trimethyldeca-2,4,8-trien-1-ol

Guidance literature:: (3Z,7E)-(5S)-9-(tert-butyldiphenylsilanyloxy)-3,5,7-trimethylocta-3,7-dien-1-yne; With Schwartz's reagent; In dichloromethane; at 23 ℃; for 0.166667h;

With dimethyl zinc(II); In dichloromethane; at -65 ℃; for 0.25h;

3-phenylsulfanyl-propionaldehyde; In dichloromethane; at 0 ℃; for 1.5h; Further stages.;
DOI:10.1021/ol015753k

Reference yield:

: 343262-94-2
(2Z,6E)-(4S)-8-(tert-butyldiphenylsilanyloxy)-2,4,6-trimethylocta-2,6-dienal

: 343262-72-6
(6S)-(2E,4Z,8E)-1-(benzenesulfanyl-ethyl)-10-(tert-butyldiphenylsilanyloxy)-4,6,8-trimethyldeca-2,4,8-trien-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: triphenylphosphine / CH₂Cl₂ / 0.17 h / 0 °C

1.2: 1.05 g / n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 0.17 h / 23 °C

2.2: Me₂Zn / CH₂Cl₂ / 0.25 h / -65 °C

2.3: 92 percent / CH₂Cl₂ / 1.5 h / 0 °C

With Schwartz's reagent; triphenylphosphine; In dichloromethane;
DOI:10.1021/ol015753k

Reference yield:

: 343262-68-0
(2S)-(4E)-6-(tert-butyldiphenylsilanyloxy)-2,4-dimethyl-hex-4-enal

: 343262-72-6
(6S)-(2E,4Z,8E)-1-(benzenesulfanyl-ethyl)-10-(tert-butyldiphenylsilanyloxy)-4,6,8-trimethyldeca-2,4,8-trien-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / potassium bis(trimethylsilyl)amide; 18-crown-6 / tetrahydrofuran; toluene / 2 h / -78 °C

2.1: 98 percent / DIBAL / diethyl ether / 1.5 h / -78 - 20 °C

3.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 0.75 h / -78 °C

4.1: triphenylphosphine / CH₂Cl₂ / 0.17 h / 0 °C

4.2: 1.05 g / n-BuLi / tetrahydrofuran / 1 h / -78 °C

5.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 0.17 h / 23 °C

5.2: Me₂Zn / CH₂Cl₂ / 0.25 h / -65 °C

5.3: 92 percent / CH₂Cl₂ / 1.5 h / 0 °C

With Schwartz's reagent; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol015753k