2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethylcyclohexanone

Base Information

• Chemical Name: 2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethylcyclohexanone
• CAS No.: 131691-34-4
• Molecular Formula: C₁₇H₃₄O₂Si
• Molecular Weight: 298.541
• Mol file: 131691-34-4.mol

Synonyms:2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethylcyclohexanone

Chemical Property of 2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethylcyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethylcyclohexanone

There total 5 articles about 2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethylcyclohexanone 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: 58.0%

(2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-one (131691-33-3) + methyl iodide (74-88-4) → 2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethylcyclohexanone (131691-34-4)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; hexane; for 0.416667h; Ambient temperature;

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

Reference yield:

(1R,3R,4S,8R)-9-hydroxy-p-menthol (13834-07-6) → 2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethylcyclohexanone (131691-34-4)

Guidance literature:

Multi-step reaction with 3 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

With dmap; oxalyl dichloride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

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

Reference yield:

(1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol (131691-32-2) → 2S-(1'-t-butyldimethylsilyloxy-2'R-propyl)-5R,6S-dimethylcyclohexanone (131691-34-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 58 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 0.42 h / Ambient temperature

With oxalyl dichloride; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

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

upstream raw materials:

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

methyl iodide

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

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

Downstream raw materials:

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

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

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