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

Base Information

Chemical Name:(2E,4E)-(9S,11S)-12-<(tert-Butyldimethylsilyl)oxy>-3,9,11-trimethyl-1-(benzyloxy)-2,4-dodecadien-6-yn-8-one
CAS No.:125496-03-9
Molecular Formula:C₂₈H₄₂O₃Si
Molecular Weight:454.725
Hs Code.:

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

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

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

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

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

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1021/jo00295a030

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:

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

: 125590-07-0
(2E,8E,10E,12E)-(4S,6S,7S)-Methyl 7,14-bis(benzyloxy)-2,4,6,12-tetramethyltetradeca-2,8,10,12-tetraenoate

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / (1R,2S)-4-(dimethylamino)-3-methyl-1,2-diphenyl-2-butanol, LiAlH₄ / tetrahydrofuran; diethyl ether / 3 h / -78 °C / other hydrides, other temperatures

2: 92 percent / 1a) Red-Al / diethyl ether; toluene / 1a) 0 deg C, 40 min, 1b) 0 deg C, 45 min, 1b) r.t., 1.75h

3: 85 percent Chromat_. / n-BuLi, HMPA / tetrahydrofuran / 0.5 h / -78 °C

4: 93 percent Chromat_. / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

5: 88 percent Chromat_. / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.67 h / -78 °C

6: 88 percent Chromat_. / CH₂Cl₂ / 1) 0 deg C, 45 min, 2) r.t., 45h

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; (+)-4-dimethylamino-1,2-diphenyl-3-methyl-2-butanol; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo00295a030