(5R,6R)-6-acetyl-6-((E)-5-(tert-butyldimethylsilyloxy)-4-methylhexa-3,5-dienyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

Base Information

Chemical Name:(5R,6R)-6-acetyl-6-((E)-5-(tert-butyldimethylsilyloxy)-4-methylhexa-3,5-dienyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone
CAS No.:397870-42-7
Molecular Formula:C₂₅H₄₀O₃Si
Molecular Weight:416.676
Hs Code.:

Synonyms:(5R,6R)-6-acetyl-6-((E)-5-(tert-butyldimethylsilyloxy)-4-methylhexa-3,5-dienyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

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Chemical Property of (5R,6R)-6-acetyl-6-((E)-5-(tert-butyldimethylsilyloxy)-4-methylhexa-3,5-dienyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

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Technology Process of (5R,6R)-6-acetyl-6-((E)-5-(tert-butyldimethylsilyloxy)-4-methylhexa-3,5-dienyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

There total 6 articles about (5R,6R)-6-acetyl-6-((E)-5-(tert-butyldimethylsilyloxy)-4-methylhexa-3,5-dienyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-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: 90.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 397870-41-6
(5R,6R)-6-acetyl-2-methyl-6-((E)-4-methyl-5-oxohex-3-enyl)-5-(prop-1-en-2-yl)cyclohex-2-enone

: 397870-42-7
(5R,6R)-6-acetyl-6-((E)-5-(tert-butyldimethylsilyloxy)-4-methylhexa-3,5-dienyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

Guidance literature:: With triethylamine; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(01)01953-0

Reference yield:

: 338387-14-7
3-((1R,6R)-1-Acetyl-6-isopropenyl-3-methyl-2-oxo-cyclohex-3-enyl)-propionaldehyde

: 397870-42-7
(5R,6R)-6-acetyl-6-((E)-5-(tert-butyldimethylsilyloxy)-4-methylhexa-3,5-dienyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C

1.2: 83 percent / tetrahydrofuran / 0.5 h / -50 °C

2.1: 90 percent / triethylamine / CH₂Cl₂ / 1 h / -78 °C

With sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; 1.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/j.tet.2006.11.083

Reference yield:

: 2244-16-8,6485-40-1
(S)-p-mentha-6,8-dien-2-one

: 397870-42-7
(5R,6R)-6-acetyl-6-((E)-5-(tert-butyldimethylsilyloxy)-4-methylhexa-3,5-dienyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enone

Guidance literature:: Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran / -78 °C

2.1: (ClCO)2; DMSO; Et₃N / CH₂Cl₂ / -30 °C

3.1: NaH / tetrahydrofuran / 0 °C

3.2: 78 percent / Bu₄NHSO₄ / tetrahydrofuran

4.1: 92 percent / pyridinium p-toluenesulfonate / acetone; H₂O

5.1: 83 percent / tetrahydrofuran / 20 °C

6.1: 90 percent / Et₃N / CH₂Cl₂ / -78 °C

With oxalyl dichloride; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; acetone; 2.1: Swern oxidation;
DOI:10.1016/S0040-4039(01)01953-0