(5E,9E)-4-<(Triisopropylsilyl)oxy>-6,10,14-trimethyl-5,9,13-pentadecatrien-1-yne

Base Information

Chemical Name:(5E,9E)-4-<(Triisopropylsilyl)oxy>-6,10,14-trimethyl-5,9,13-pentadecatrien-1-yne
CAS No.:149797-94-4
Molecular Formula:C₂₇H₄₈OSi
Molecular Weight:416.763
Hs Code.:

Synonyms:(5E,9E)-4-<(Triisopropylsilyl)oxy>-6,10,14-trimethyl-5,9,13-pentadecatrien-1-yne

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (5E,9E)-4-<(Triisopropylsilyl)oxy>-6,10,14-trimethyl-5,9,13-pentadecatrien-1-yne

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Technology Process of (5E,9E)-4-<(Triisopropylsilyl)oxy>-6,10,14-trimethyl-5,9,13-pentadecatrien-1-yne

There total 1 articles about (5E,9E)-4-<(Triisopropylsilyl)oxy>-6,10,14-trimethyl-5,9,13-pentadecatrien-1-yne 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: 94.0%

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 149797-93-3
(5E,9E)-6,10,14-Trimethyl-5,9,13-pentadecatrien-1-yn-4-ol

: 149797-94-4
(5E,9E)-4-<(Triisopropylsilyl)oxy>-6,10,14-trimethyl-5,9,13-pentadecatrien-1-yne

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1021/jo00067a024

Reference yield:

: 149797-94-4
(5E,9E)-4-<(Triisopropylsilyl)oxy>-6,10,14-trimethyl-5,9,13-pentadecatrien-1-yne

: rel-(1R,2R,6S,7E,11E)-1-Isopropenyl-2-(benzoyloxy)-8,12-dimethyl-7,11-cyclotetradecadien-3-yn-6-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 1 h, 2) room temp., 0.5 h

2: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl_2. -78 deg C, 30 min, 2) 0 deg C, 15 min

3: 61 percent / EtAlCl₂ / CH₂Cl₂; hexane / 0.83 h / -78 °C

4: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min, 2) 0 deg C, 15 min

5: 79 percent / L-Selectride / tetrahydrofuran / 1 h / -78 °C

6: 81 percent / triphenylphosphine, diisopropyl azodicarboxylate / benzene / 5 h

7: 84 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

With n-butyllithium; oxalyl dichloride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; ethylaluminum dichloride; L-Selectride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; benzene;
DOI:10.1021/jo00067a024

Reference yield:

: 149797-94-4
(5E,9E)-4-<(Triisopropylsilyl)oxy>-6,10,14-trimethyl-5,9,13-pentadecatrien-1-yne

: rel-(1R,2R,6S,7E,11E)-1-Isopropenyl-2-(benzoyloxy)-6-<(tert-butyldimethylsilyl)oxy>-8,12-dimethyl-7,11-cyclotetradecadien-3-yne

Guidance literature:: Multi-step reaction with 8 steps

1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 1 h, 2) room temp., 0.5 h

2: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl_2. -78 deg C, 30 min, 2) 0 deg C, 15 min

3: 61 percent / EtAlCl₂ / CH₂Cl₂; hexane / 0.83 h / -78 °C

4: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 30 min, 2) 0 deg C, 15 min

5: 79 percent / L-Selectride / tetrahydrofuran / 1 h / -78 °C

6: 81 percent / triphenylphosphine, diisopropyl azodicarboxylate / benzene / 5 h

7: 84 percent / TBAF / tetrahydrofuran / 1 h / Ambient temperature

8: 86 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

With 1H-imidazole; n-butyllithium; oxalyl dichloride; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; ethylaluminum dichloride; L-Selectride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00067a024