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

Base Information

• Chemical Name: (R)-2-{(1S,4R)-4-Methyl-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propan-1-ol
• CAS No.: 131691-37-7
• Molecular Formula: C₁₄H₂₈OSi
• Molecular Weight: 240.461

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

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

Chemical Property:

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

There total 5 articles about (R)-2-{(1S,4R)-4-Methyl-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propan-1-ol 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: 94.0%

(1S,4R)-1-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-methyl-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexane (131691-35-5) → (R)-2-{(1S,4R)-4-Methyl-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propan-1-ol (131691-37-7)

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) → (R)-2-{(1S,4R)-4-Methyl-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propan-1-ol (131691-37-7)

Guidance literature:

Multi-step reaction with 4 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

With dmap; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1039/c39900001487

Reference yield:

(1R,2S,5R)-2-[((R)-2'-tert-butyldimethylsilyloxy)-1'-methylethyl]-5-methylcyclohexan-1-ol (131691-32-2) → (R)-2-{(1S,4R)-4-Methyl-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexyl}-propan-1-ol (131691-37-7)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 39 percent / pentane

3: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran

With oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pentane;

DOI:10.1039/c39900001487

upstream raw materials:

(1S,4R)-1-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-methyl-2-[1-trimethylsilanyl-meth-(E)-ylidene]-cyclohexane

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

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