5R-methyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane

Base Information

• Chemical Name: 5R-methyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane
• CAS No.: 131691-39-9
• Molecular Formula: C₁₄H₂₆O₂Si
• Molecular Weight: 254.445
• Mol file: 131691-39-9.mol

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

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

There total 6 articles about 5R-methyl-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: 93.0%

(R)-2-{(1S,4R)-4-Methyl-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propan-1-ol (131691-37-7) → 5R-methyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane (131691-39-9)

Guidance literature:

With dipyridinium dichromate; In N,N-dimethyl-formamide;

DOI:10.1039/c39900001487

Reference yield:

(1R,3R,4S,8R)-9-hydroxy-p-menthol (13834-07-6) → 5R-methyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane (131691-39-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 4-N,N-dimethylaminopyridine / CH₂Cl₂

2: 1.) (COCl)2, DMSO, 2.) Et₃N / Swern oxidation

3: 39 percent / pentane

4: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

5: 93 percent / pyridinium dichromate / dimethylformamide

With dmap; dipyridinium dichromate; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; pentane;

DOI:10.1039/c39900001487

Reference yield:

(1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol (131691-32-2) → 5R-methyl-2S-(2'R-propionyl)-1(E/Z)-trimethylsilylmethylenecyclohexane (131691-39-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / Swern oxidation

2: 39 percent / pentane

3: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

4: 93 percent / pyridinium dichromate / dimethylformamide

With dipyridinium dichromate; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; pentane;

DOI:10.1039/c39900001487

upstream raw materials:

(R)-2-{(1S,4R)-4-Methyl-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propan-1-ol

(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