(S)-5-((tert-butyldimethylsilyl)oxy)-3-((1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-2,4,4-trimethylcyclohex-2-enone

Base Information

Chemical Name:(S)-5-((tert-butyldimethylsilyl)oxy)-3-((1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-2,4,4-trimethylcyclohex-2-enone
CAS No.:1449674-42-3
Molecular Formula:C₂₁H₃₆O₃Si
Molecular Weight:364.601
Hs Code.:

Synonyms:(S)-5-((tert-butyldimethylsilyl)oxy)-3-((1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-2,4,4-trimethylcyclohex-2-enone

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Chemical Property of (S)-5-((tert-butyldimethylsilyl)oxy)-3-((1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-2,4,4-trimethylcyclohex-2-enone

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Technology Process of (S)-5-((tert-butyldimethylsilyl)oxy)-3-((1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-2,4,4-trimethylcyclohex-2-enone

There total 16 articles about (S)-5-((tert-butyldimethylsilyl)oxy)-3-((1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-2,4,4-trimethylcyclohex-2-enone 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: 81.0%

: 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

: 1449674-42-3
(S)-5-((tert-butyldimethylsilyl)oxy)-3-((1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-2,4,4-trimethylcyclohex-2-enone

Guidance literature:: With zinc(II) tetrahydroborate; In tetrahydrofuran; at -40 ℃; for 2h; 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

: 1449674-42-3
(S)-5-((tert-butyldimethylsilyl)oxy)-3-((1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-2,4,4-trimethylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 4 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

4.1: zinc(II) tetrahydroborate / tetrahydrofuran / 2 h / -40 °C

With n-butyllithium; zinc(II) tetrahydroborate; 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

: 1449674-42-3
(S)-5-((tert-butyldimethylsilyl)oxy)-3-((1E,3E)-5-hydroxy-3-methylpenta-1,3-dien-1-yl)-2,4,4-trimethylcyclohex-2-enone

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: zinc(II) tetrahydroborate / tetrahydrofuran / 2 h / -40 °C

With zinc(II) tetrahydroborate; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1039/c3ob41226a