(2R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(R)-1-hydroxy-3-benzyloxypropyl]-6-methylcyclohexanone

Base Information

• Chemical Name: (2R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(R)-1-hydroxy-3-benzyloxypropyl]-6-methylcyclohexanone
• CAS No.: 187665-48-1
• Molecular Formula: C₂₀H₂₇ClO₃
• Molecular Weight: 350.886
• Mol file: 187665-48-1.mol

Synonyms:(2R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(R)-1-hydroxy-3-benzyloxypropyl]-6-methylcyclohexanone

Chemical Property of (2R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(R)-1-hydroxy-3-benzyloxypropyl]-6-methylcyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(R)-1-hydroxy-3-benzyloxypropyl]-6-methylcyclohexanone

There total 3 articles about (2R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(R)-1-hydroxy-3-benzyloxypropyl]-6-methylcyclohexanone 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: 75.0%

3-Benzyloxypropanal (19790-60-4) + (2R,5R)-5-(1-chloromethylethenyl)-2-methylcyclohexanone (187665-47-0) → (2R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(R)-1-hydroxy-3-benzyloxypropyl]-6-methylcyclohexanone (187665-48-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1055/s-1997-748

Reference yield:

(2R,5R)-5-isopropenyl-2-methylcyclohexanone (5524-05-0) → (2R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(R)-1-hydroxy-3-benzyloxypropyl]-6-methylcyclohexanone (187665-48-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 55 percent

2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 75 percent / tetrahydrofuran / 1 h / -78 °C

With lithium diisopropyl amide; In tetrahydrofuran; hexane; 1.1: Chlorination / 2.1: Metallation / 2.2: Condensation;

DOI:10.1016/S0040-4020(99)00885-6

Reference yield:

benzaldehyde (100-52-7) → (2R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(R)-1-hydroxy-3-benzyloxypropyl]-6-methylcyclohexanone (187665-48-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 77 percent

2.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 75 percent / tetrahydrofuran / 1 h / -78 °C

With lithium diisopropyl amide; In tetrahydrofuran; hexane; 1.1: Cycloaddition / 1.2: Ring cleavage / 1.3: Oxidation / 2.1: Metallation / 2.2: Condensation;

DOI:10.1016/S0040-4020(99)00885-6

upstream raw materials:

3-Benzyloxypropanal

(2R,5R)-5-(1-chloromethylethenyl)-2-methylcyclohexanone

(2R,5R)-5-isopropenyl-2-methylcyclohexanone

benzaldehyde

Downstream raw materials:

(1S,4R,7R,8R)-11-[(E)-3-benzyloxypropylidene]-7-(methoxymethoxy)-8-methyl-2-methylenebicyclo[5.3.1]undecan-4-ol

(1R,3R,6R)-1-allyl-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-6-methyl-1-cyclohexanol

(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanal

(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol