(2R,3S,4S)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-isopropenyl-3-{[(p-methoxyphenyl)methoxy]methyl}-2-methylcyclopentanone

Base Information

Chemical Name:(2R,3S,4S)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-isopropenyl-3-{[(p-methoxyphenyl)methoxy]methyl}-2-methylcyclopentanone
CAS No.:1621399-21-0
Molecular Formula:C₂₈H₄₀O₃
Molecular Weight:424.624
Hs Code.:

Synonyms:(2R,3S,4S)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-isopropenyl-3-{[(p-methoxyphenyl)methoxy]methyl}-2-methylcyclopentanone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3S,4S)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-isopropenyl-3-{[(p-methoxyphenyl)methoxy]methyl}-2-methylcyclopentanone

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Technology Process of (2R,3S,4S)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-isopropenyl-3-{[(p-methoxyphenyl)methoxy]methyl}-2-methylcyclopentanone

There total 6 articles about (2R,3S,4S)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-isopropenyl-3-{[(p-methoxyphenyl)methoxy]methyl}-2-methylcyclopentanone 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: 80.0%

: C₃₀H₄₄O₅

: 1621399-21-0
(2R,3S,4S)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-isopropenyl-3-{[(p-methoxyphenyl)methoxy]methyl}-2-methylcyclopentanone

Guidance literature:: With samarium diiodide; In tetrahydrofuran; methanol; toluene; for 0.25h; Inert atmosphere; Molecular sieve;
DOI:10.1055/s-0033-1338573

Reference yield:

: 1621399-34-5
(2R,3S,4S)-4-isopropenyl-3-{[(p-methoxyphenyl)methoxy]-methyl}-2-methylcyclopentanone

: 5389-87-7
1-chloro-3,7-dimethylocta-2,6-diene

: 1621399-21-0
(2R,3S,4S)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-isopropenyl-3-{[(p-methoxyphenyl)methoxy]methyl}-2-methylcyclopentanone

: C₂₈H₄₀O₃

: C₃₈H₅₆O₃

Guidance literature:: (2R,3S,4S)-4-isopropenyl-3-{[(p-methoxyphenyl)methoxy]-methyl}-2-methylcyclopentanone; With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; for 0.666667h; Inert atmosphere;

1-chloro-3,7-dimethylocta-2,6-diene; In tetrahydrofuran; toluene; at 40 ℃; for 1h; Overall yield = ~ 55 %; regioselective reaction;
DOI:10.1055/s-0033-1338573

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 1621399-21-0
(2R,3S,4S)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-isopropenyl-3-{[(p-methoxyphenyl)methoxy]methyl}-2-methylcyclopentanone

: C₂₈H₄₀O₃

: C₃₈H₅₆O₃

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

1.2: 2.67 h

2.1: pyridinium p-toluenesulfonate / methanol / 15 h

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h / -84 °C / Inert atmosphere

3.2: 1.75 h / 0 °C

4.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 0.67 h / Inert atmosphere

4.2: 1 h / 40 °C

With oxalyl dichloride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;
DOI:10.1055/s-0033-1338573