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

Base Information

Chemical Name:(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanal
CAS No.:187665-53-8
Molecular Formula:C₂₅H₃₅ClO₄
Molecular Weight:435.003
Hs Code.:

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

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

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

There total 10 articles about (1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanal 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%

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

: 187665-53-8
(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanal

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(99)00885-6

Reference yield:

: 187665-47-0
(2R,5R)-5-(1-chloromethylethenyl)-2-methylcyclohexanone

: 187665-53-8
(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanal

Guidance literature:: Multi-step reaction with 6 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

6.1: 90 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; dmap; Thexylboran; 1-methyl-2-fluoropyridinium p-toluenesulfonate; Dess-Martin periodane; 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 / 6.1: Oxidation;
DOI:10.1016/S0040-4020(99)00885-6

Reference yield:

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

: 187665-53-8
(1R,3R,6R)-3-[1-(chloromethyl)ethenyl]-2-[(E)-3-benzyloxypropylidene]-1-(methoxymethoxy)-6-methylcyclohexane propanal

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 90 percent / aq. NaOH; aq. H₂O / 5 h / 20 °C

2.1: 90 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; Thexylboran; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1.1: hydroboration / 1.2: Oxidation / 2.1: Oxidation;
DOI:10.1016/S0040-4020(99)00885-6