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

Base Information

Chemical Name:(2E,4E,6E)-(8S,9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4,6-dodecatrien-8-ol
CAS No.:125590-04-7
Molecular Formula:C₂₈H₄₆O₃Si
Molecular Weight:458.757
Hs Code.:

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

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

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

There total 10 articles about (2E,4E,6E)-(8S,9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4,6-dodecatrien-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: 92.0%

: 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

: 125590-04-7
(2E,4E,6E)-(8S,9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4,6-dodecatrien-8-ol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; toluene; 1a) 0 deg C, 40 min, 1b) 0 deg C, 45 min, 1b) r.t., 1.75h;
DOI:10.1021/jo00295a030

Reference yield:

: 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

: 101376-79-8,101469-60-7,125590-04-7
(6E,8E,10E)-(2R,4R)-12-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-2,4,10-trimethyl-dodeca-6,8,10-trien-5-ol

Guidance literature:: With sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; at 0 - 23 ℃;
DOI:10.1021/jo00359a060

Reference yield:

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

: 101376-79-8,101469-60-7,125590-04-7
(6E,8E,10E)-(2R,4R)-12-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-2,4,10-trimethyl-dodeca-6,8,10-trien-5-ol

Guidance literature:: Multi-step reaction with 6 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

6: red-Al / diethyl ether / 0 - 23 °C

With n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo00359a060