(5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-cyclohex-2-enone

Base Information

• Chemical Name: (5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-cyclohex-2-enone
• CAS No.: 423764-38-9
• Molecular Formula: C₁₆H₂₈O₂Si
• Molecular Weight: 280.483
• Mol file: 423764-38-9.mol

Synonyms:(5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-cyclohex-2-enone

Chemical Property of (5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-cyclohex-2-enone

There total 1 articles about (5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-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:

tert-butyldimethylsilyl chloride (18162-48-6) + {[(3S)-3-isopropenyl-6-methyl-cyclohexa-1,5-dienyl]oxy}(trimethyl)silane (423764-66-3) → (5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-cyclohex-2-enone (423764-38-9)

Guidance literature:

{[(3S)-3-isopropenyl-6-methyl-cyclohexa-1,5-dienyl]oxy}(trimethyl)silane; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 1h;

In acetonitrile; at 20 ℃; for 0.5h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 10h; Further stages.;

DOI:10.1021/jo010752r

Reference yield: 70.0%

tetravinyltin (IV) (1112-56-7) + (5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-cyclohex-2-enone (423764-38-9) → (1S,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-1-vinyl-cyclohex-2-enol (423764-39-0)

Guidance literature:

tetravinyltin (IV); With n-butyllithium; In tetrahydrofuran; at 20 ℃; for 1h;

(5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-cyclohex-2-enone; In tetrahydrofuran; at 20 ℃; for 6h; Further stages.;

DOI:10.1021/jo010752r

Reference yield:

(5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-cyclohex-2-enone (423764-38-9) → (1R,2S,6R)-6-Isopropenyl-3-methyl-2-vinyl-cyclohex-3-ene-1,2-diol (423764-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / 1 h / 20 °C

1.2: 70 percent / tetrahydrofuran / 6 h / 20 °C

2.1: 90 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/jo010752r

upstream raw materials:

tert-butyldimethylsilyl chloride

{[(3S)-3-isopropenyl-6-methyl-cyclohexa-1,5-dienyl]oxy}(trimethyl)silane

Downstream raw materials:

(1S,5R,6R)-6-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-2-methyl-1-vinyl-cyclohex-2-enol

(1R,2S,6R)-6-Isopropenyl-3-methyl-2-vinyl-cyclohex-3-ene-1,2-diol

(1S,5R,6R)-5-Isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-1-vinyl-cyclohex-2-enol

Isobutyric acid (1S,5R,6R)-5-isopropenyl-6-(2-methoxy-ethoxymethoxy)-2-methyl-1-vinyl-cyclohex-2-enyl ester