(2E,4E)-(8S,9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4-dodecadien-6-yn-8-ol

Base Information

Chemical Name:(2E,4E)-(8S,9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4-dodecadien-6-yn-8-ol
CAS No.:125590-03-6
Molecular Formula:C₂₈H₄₄O₃Si
Molecular Weight:456.741
Hs Code.:

Synonyms:(2E,4E)-(8S,9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4-dodecadien-6-yn-8-ol

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Chemical Property of (2E,4E)-(8S,9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4-dodecadien-6-yn-8-ol

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Technology Process of (2E,4E)-(8S,9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4-dodecadien-6-yn-8-ol

There total 9 articles about (2E,4E)-(8S,9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4-dodecadien-6-yn-8-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: 89.0%

: 125496-03-9
(2E,4E)-(9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4-dodecadien-6-yn-8-one

: 125590-03-6
(2E,4E)-(8S,9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4-dodecadien-6-yn-8-ol

Guidance literature:: With lithium aluminium tetrahydride; (+)-4-dimethylamino-1,2-diphenyl-3-methyl-2-butanol; In tetrahydrofuran; diethyl ether; at -78 ℃; for 3h; other hydrides, other temperatures;
DOI:10.1021/jo00295a030

Reference yield:

: 70238-41-4
(E)-4-(benzyloxy)-2-methylbut-2-en-1-ol

: 101376-78-7,101469-59-4,125590-03-6,125590-11-6
(8E,10E)-(2R,4R)-12-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-2,4,10-trimethyl-dodeca-8,10-dien-6-yn-5-ol

Guidance literature:: Multi-step reaction with 5 steps

1: (COCl)2, Me₂SO, Et₃N / CH₂Cl₂

2: -78 °C

3: Bu₄NF / tetrahydrofuran / 0 - 23 °C

4: n-BuLi / tetrahydrofuran / -78 °C

5: tetrahydrofuran / -40 °C

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo00359a060

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 101376-78-7,101469-59-4,125590-03-6,125590-11-6
(8E,10E)-(2R,4R)-12-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-2,4,10-trimethyl-dodeca-8,10-dien-6-yn-5-ol

Guidance literature:: Multi-step reaction with 7 steps

1: CH₂Cl₂

2: DIBAH / diethyl ether / -78 °C

3: (COCl)2, Me₂SO, Et₃N / CH₂Cl₂

4: -78 °C

5: Bu₄NF / tetrahydrofuran / 0 - 23 °C

6: n-BuLi / tetrahydrofuran / -78 °C

7: tetrahydrofuran / -40 °C

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo00359a060