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

Base Information

• Chemical Name: (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol
• CAS No.: 187665-52-7
• Molecular Formula: C₂₅H₃₇ClO₄
• Molecular Weight: 437.019
• Mol file: 187665-52-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol 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: 90.0%

(1R,3R,6R)-1-allyl-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane (187665-51-6) → (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol (187665-52-7)

Guidance literature:

(1R,3R,6R)-1-allyl-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane; With Thexylboran; In tetrahydrofuran; at -10 ℃; for 1h;

With sodium hydroxide; water; at 20 ℃; for 5h;

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

Reference yield:

(2R,5R)-5-(1-chloromethylethenyl)-2-methylcyclohexanone (187665-47-0) → (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol (187665-52-7)

Guidance literature:

Multi-step reaction with 5 steps

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

1.2: 75 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 85 percent / Et₃N; 2-fluoro-1-methylpyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / 50 °C

3.1: 81 percent / diethyl ether / 0.5 h / -78 °C

4.1: 91 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 96 h / 20 °C

5.1: thexylBH₂ / tetrahydrofuran / 1 h / -10 °C

5.2: 90 percent / aq. NaOH; aq. H₂O / 5 h / 20 °C

With dmap; Thexylboran; 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Metallation / 1.2: Condensation / 2.1: Elimination / 3.1: Grignard reaction / 4.1: Etherification / 5.1: hydroboration / 5.2: Oxidation;

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

Reference yield:

(3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-6-methylcyclohexanone (187665-49-2) → (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanol (187665-52-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 81 percent / diethyl ether / 0.5 h / -78 °C

2.1: 91 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 96 h / 20 °C

3.1: thexylBH₂ / tetrahydrofuran / 1 h / -10 °C

3.2: 90 percent / aq. NaOH; aq. H₂O / 5 h / 20 °C

With dmap; Thexylboran; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Grignard reaction / 2.1: Etherification / 3.1: hydroboration / 3.2: Oxidation;

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

upstream raw materials:

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

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

3-Benzyloxypropanal

benzaldehyde

Downstream raw materials:

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

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