(2E,4R,5R,6E,8E,10S,11R,12S)-2-iodo-4,6,8,10,12-pentamethyl-5-(triphenylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatriene

Base Information

Chemical Name:(2E,4R,5R,6E,8E,10S,11R,12S)-2-iodo-4,6,8,10,12-pentamethyl-5-(triphenylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatriene
CAS No.:637741-09-4
Molecular Formula:C₅₃H₇₁IO₃Si
Molecular Weight:911.135
Hs Code.:

Synonyms:(2E,4R,5R,6E,8E,10S,11R,12S)-2-iodo-4,6,8,10,12-pentamethyl-5-(triphenylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatriene

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Chemical Property of (2E,4R,5R,6E,8E,10S,11R,12S)-2-iodo-4,6,8,10,12-pentamethyl-5-(triphenylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatriene

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Technology Process of (2E,4R,5R,6E,8E,10S,11R,12S)-2-iodo-4,6,8,10,12-pentamethyl-5-(triphenylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatriene

There total 7 articles about (2E,4R,5R,6E,8E,10S,11R,12S)-2-iodo-4,6,8,10,12-pentamethyl-5-(triphenylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatriene 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: 82.0%

: 637741-08-3
(4R,5R,6E,8E,10S,11R,12S)-4,6,8,10,12-pentamethyl-5-(triphenylsiloxy)-11-(4-methoxybenzyloxy)-6,8-docosadiene-2-yne

: 637741-09-4
(2E,4R,5R,6E,8E,10S,11R,12S)-2-iodo-4,6,8,10,12-pentamethyl-5-(triphenylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatriene

Guidance literature:: (4R,5R,6E,8E,10S,11R,12S)-4,6,8,10,12-pentamethyl-5-(triphenylsiloxy)-11-(4-methoxybenzyloxy)-6,8-docosadiene-2-yne; With zirconocene hydrochloride; In tetrahydrofuran; at 50 ℃; for 1h;

With iodine; In tetrahydrofuran; at 0 ℃; for 0.0833333h; Further stages.;
DOI:10.1039/b305818b

Reference yield:

: 361525-06-6
1-Methoxy-4-[(1R,2S)-2-methyl-1-((S)-1-methyl-but-2-ynyl)-dodecyloxymethyl]-benzene

: 637741-09-4
(2E,4R,5R,6E,8E,10S,11R,12S)-2-iodo-4,6,8,10,12-pentamethyl-5-(triphenylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatriene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C

1.2: K₃PO₄ / PdCl₂(dppf) / dimethylformamide; tetrahydrofuran; H₂O / 0.33 h / 65 °C

2.1: 1.18 g / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.33 h / -78 °C

3.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

4.1: 1.11 g / triphenylphosphine / CH₂Cl₂ / 0.08 h / 0 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 91 percent / tetrahydrofuran; hexane / 0.5 h / 20 °C

6.1: zirconocene hydrochloride / tetrahydrofuran / 1 h / 50 °C

6.2: 82 percent / I₂ / tetrahydrofuran / 0.08 h / 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; zirconocene hydrochloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; 1.2: Suzuki-Miyaura coupling / 3.1: Swern oxidation;
DOI:10.1039/b305818b

Reference yield:

: 361525-01-1
(E)-(2S,3R)-5-Iodo-2,4-dimethyl-3-triphenylsilanyloxy-pent-4-enoic acid phenyl ester

: 637741-09-4
(2E,4R,5R,6E,8E,10S,11R,12S)-2-iodo-4,6,8,10,12-pentamethyl-5-(triphenylsiloxy)-11-(4-methoxybenzyloxy)-2,6,8-docosatriene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C

1.2: K₃PO₄ / PdCl₂(dppf) / dimethylformamide; tetrahydrofuran; H₂O / 0.33 h / 65 °C

2.1: 1.18 g / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.33 h / -78 °C

3.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

4.1: 1.11 g / triphenylphosphine / CH₂Cl₂ / 0.08 h / 0 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 91 percent / tetrahydrofuran; hexane / 0.5 h / 20 °C

6.1: zirconocene hydrochloride / tetrahydrofuran / 1 h / 50 °C

6.2: 82 percent / I₂ / tetrahydrofuran / 0.08 h / 0 °C

With 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; zirconocene hydrochloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; 1.2: Suzuki-Miyaura coupling / 3.1: Swern oxidation;
DOI:10.1039/b305818b