(2E,4E)-5-((S)-5-((tert-butyldimethylsilyl)oxy)-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal

Base Information

Chemical Name:(2E,4E)-5-((S)-5-((tert-butyldimethylsilyl)oxy)-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal
CAS No.:1449674-41-2
Molecular Formula:C₂₁H₃₄O₃Si
Molecular Weight:362.585
Hs Code.:

Synonyms:(2E,4E)-5-((S)-5-((tert-butyldimethylsilyl)oxy)-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal

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Chemical Property of (2E,4E)-5-((S)-5-((tert-butyldimethylsilyl)oxy)-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal

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Technology Process of (2E,4E)-5-((S)-5-((tert-butyldimethylsilyl)oxy)-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal

There total 15 articles about (2E,4E)-5-((S)-5-((tert-butyldimethylsilyl)oxy)-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal 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: 84.0%

: 1449674-40-1
(2E,4E)-5-((3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal

: 1449674-41-2
(2E,4E)-5-((S)-5-((tert-butyldimethylsilyl)oxy)-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.25h; chemoselective reaction;
DOI:10.1039/c3ob41226a

Reference yield:

: 1449674-39-8
(3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-enecarbaldehyde

: 1449674-41-2
(2E,4E)-5-((S)-5-((tert-butyldimethylsilyl)oxy)-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 20 °C

1.2: 2 h / 0 - 20 °C

2.1: diisobutylaluminium hydride / toluene / 6 h / -20 - 20 °C

3.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

With n-butyllithium; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; toluene; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1039/c3ob41226a

Reference yield:

: 1449674-32-1
(2E,4E)-5-((3R,5S)-5-((tert-butyldimethylsilyl)oxy)-3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3-methylpenta-2,4-dienenitrile

: 1449674-41-2
(2E,4E)-5-((S)-5-((tert-butyldimethylsilyl)oxy)-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3-methylpenta-2,4-dienal

Guidance literature:: Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / toluene / 6 h / -20 - 20 °C

2: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C

With diisobutylaluminium hydride; Dess-Martin periodane; In dichloromethane; toluene;
DOI:10.1039/c3ob41226a