1,8-Dodecadien-4-ol, 6,10-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxy-12-[(4-methoxy phenyl)methoxy]-7,9-dimethyl-, (3R,4R,6S,7S,8E,10S)-

Base Information

Chemical Name:1,8-Dodecadien-4-ol, 6,10-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxy-12-[(4-methoxy phenyl)methoxy]-7,9-dimethyl-, (3R,4R,6S,7S,8E,10S)-
CAS No.:875439-66-0
Molecular Formula:C35H64O6Si2
Molecular Weight:637.061
Hs Code.:

1,8-Dodecadien-4-ol,
6,10-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxy-12-[(4-methoxy
phenyl)methoxy]-7,9-dimethyl-, (3R,4R,6S,7S,8E,10S)-

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Chemical Property of 1,8-Dodecadien-4-ol, 6,10-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxy-12-[(4-methoxy phenyl)methoxy]-7,9-dimethyl-, (3R,4R,6S,7S,8E,10S)-

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Technology Process of 1,8-Dodecadien-4-ol, 6,10-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxy-12-[(4-methoxy phenyl)methoxy]-7,9-dimethyl-, (3R,4R,6S,7S,8E,10S)-

There total 14 articles about 1,8-Dodecadien-4-ol, 6,10-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxy-12-[(4-methoxy phenyl)methoxy]-7,9-dimethyl-, (3R,4R,6S,7S,8E,10S)- 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: 62.0%

: (S)-4-Benzyl-3-[(E)-(2S,3R,5S,6S,9S)-5,9-bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methoxy-11-(4-methoxy-benzyloxy)-6,8-dimethyl-undec-7-enoyl]-oxazolidin-2-one

: 875439-66-0
(E)-(3R,4R,6S,7S,10S)-6,10-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-12-(4-methoxy-benzyloxy)-7,9-dimethyl-dodeca-1,8-dien-4-ol

Guidance literature:: DOI:10.1021/ol052588q

Reference yield:

: 875439-65-9
(E)-(3S,4S,7S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-methoxy-benzyloxy)-4,6-dimethyl-non-5-enal

: 627-40-7
methylallylether

: 875439-66-0
(E)-(3R,4R,6S,7S,10S)-6,10-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-12-(4-methoxy-benzyloxy)-7,9-dimethyl-dodeca-1,8-dien-4-ol

Guidance literature:: methylallylether; With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃;

With (-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; cyclohexane; for 1h;

(E)-(3S,4S,7S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-9-(4-methoxy-benzyloxy)-4,6-dimethyl-non-5-enal; With boron trifluoride diethyl etherate; In tetrahydrofuran; n-heptane; at -78 - 20 ℃; for 5h;
DOI:10.1021/ol052588q

Reference yield:

: 875439-77-3
(2S,3E,5S)-5-(tert-butyldimethylsilyloxy)-7-(4-methoxybenzyloxy)-2,4-dimethylhept-3-enal

: 875439-66-0
(E)-(3R,4R,6S,7S,10S)-6,10-Bis-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-12-(4-methoxy-benzyloxy)-7,9-dimethyl-dodeca-1,8-dien-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: tin(II) triflate; N-ethyl piperidine / CH₂Cl₂ / 4 h / -50 °C

1.2: 99 percent / CH₂Cl₂ / -78 °C

2.1: AlMe₃ / CH₂Cl₂; heptane / 0 - 20 °C

2.2: 95 percent / CH₂Cl₂; heptane / -30 - 20 °C

3.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h

4.1: 94 percent / DIBAL-H / toluene; hexane / 0.83 h / -78 °C

5.1: sec-BuLi / tetrahydrofuran; cyclohexane / -78 °C

5.2: (-)(ipc)2BOMe / tetrahydrofuran; cyclohexane / 1 h

5.3: BF₃*Et₂O / tetrahydrofuran; heptane / 5 h / -78 - 20 °C

With 1-ethyl-piperidine; 2,6-dimethylpyridine; tin(II) trifluoromethanesulfonate; trimethylaluminum; sec.-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; n-heptane; dichloromethane; cyclohexane; toluene; 1.2: aldol reaction;
DOI:10.1021/ol052588q