5R,6S-dimethyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane

Base Information

• Chemical Name: 5R,6S-dimethyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane
• CAS No.: 131691-38-8
• Molecular Formula: C₁₅H₃₀OSi
• Molecular Weight: 254.488
• Mol file: 131691-38-8.mol

Synonyms:5R,6S-dimethyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane

Chemical Property of 5R,6S-dimethyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5R,6S-dimethyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane

There total 6 articles about 5R,6S-dimethyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane 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: 88.0%

2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethyl-1-E/Z-trimethylsilylmethylenecyclohexane (131691-36-6) → 5R,6S-dimethyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane (131691-38-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1039/c39900001487

Reference yield:

(1R,3R,4S,8R)-9-hydroxy-p-menthol (13834-07-6) → 5R,6S-dimethyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane (131691-38-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / 4-N,N'-dimethylaminopyridine, triethylamine / CH₂Cl₂ / 18 h / Ambient temperature

2: 87 percent / dimethylsulfoxide, oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

3: 58 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 0.42 h / Ambient temperature

4: 41 percent / t-butyllithium / pentane / Ambient temperature

5: 88 percent / Bu₄NF / tetrahydrofuran / 2.5 h / 22 °C

With dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; pentane;

DOI:10.1016/S0040-4020(01)80810-3

Reference yield:

(2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-one (131691-33-3) → 5R,6S-dimethyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane (131691-38-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 0.42 h / Ambient temperature

2: 41 percent / t-butyllithium / pentane / Ambient temperature

3: 88 percent / Bu₄NF / tetrahydrofuran / 2.5 h / 22 °C

With tetrabutyl ammonium fluoride; tert.-butyl lithium; lithium diisopropyl amide; In tetrahydrofuran; hexane; pentane;

DOI:10.1016/S0040-4020(01)80810-3

upstream raw materials:

2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethyl-1-E/Z-trimethylsilylmethylenecyclohexane

(1R,3R,4S,8R)-9-hydroxy-p-menthol

(1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol

(2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-one

Downstream raw materials:

5R,6S-dimethyl-2S-(2'R-propionyl)-1-E/Z-trimethylsilylmethylenecyclohexane