(3S,4S,5S)-4-isopropenyl-5-ethoxymethoxy-3-{[(p-methoxyphenyl)methoxy]methyl}-2,2-dimethylcyclopentanone

Base Information

Chemical Name:(3S,4S,5S)-4-isopropenyl-5-ethoxymethoxy-3-{[(p-methoxyphenyl)methoxy]methyl}-2,2-dimethylcyclopentanone
CAS No.:1621399-25-4
Molecular Formula:C₂₁H₃₀O₅
Molecular Weight:362.466
Hs Code.:

Synonyms:(3S,4S,5S)-4-isopropenyl-5-ethoxymethoxy-3-{[(p-methoxyphenyl)methoxy]methyl}-2,2-dimethylcyclopentanone

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Chemical Property of (3S,4S,5S)-4-isopropenyl-5-ethoxymethoxy-3-{[(p-methoxyphenyl)methoxy]methyl}-2,2-dimethylcyclopentanone

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Technology Process of (3S,4S,5S)-4-isopropenyl-5-ethoxymethoxy-3-{[(p-methoxyphenyl)methoxy]methyl}-2,2-dimethylcyclopentanone

There total 8 articles about (3S,4S,5S)-4-isopropenyl-5-ethoxymethoxy-3-{[(p-methoxyphenyl)methoxy]methyl}-2,2-dimethylcyclopentanone 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: 54.0%

: 1621399-37-8
(2S,3S,4S,5R)-3-isopropenyl-2-methoxymethoxy-4-{[(p-methoxyphenyl)methoxy]methyl}-5-methylcyclopentanone

: 74-88-4
methyl iodide

: 1621399-25-4
(3S,4S,5S)-4-isopropenyl-5-ethoxymethoxy-3-{[(p-methoxyphenyl)methoxy]methyl}-2,2-dimethylcyclopentanone

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; toluene; at 30 ℃; for 3.5h; Temperature; Inert atmosphere;
DOI:10.1055/s-0033-1338573

Reference yield:

: 881425-05-4
[(1S,2R,3S,5S)-2-methyl-5-(prop-1-en-2-yl)-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]methanol

: 1621399-25-4
(3S,4S,5S)-4-isopropenyl-5-ethoxymethoxy-3-{[(p-methoxyphenyl)methoxy]methyl}-2,2-dimethylcyclopentanone

Guidance literature:: Multi-step reaction with 7 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: triethylamine; sodium iodide / acetonitrile / 3.08 h / 0 °C / Inert atmosphere

5.1: 2-methyl-but-2-ene; 3-chloro-benzenecarboperoxoic acid / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere

7.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 3.5 h / 30 °C / Inert atmosphere

With 2-methyl-but-2-ene; oxalyl dichloride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;
DOI:10.1055/s-0033-1338573

Reference yield:

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

: 1621399-25-4
(3S,4S,5S)-4-isopropenyl-5-ethoxymethoxy-3-{[(p-methoxyphenyl)methoxy]methyl}-2,2-dimethylcyclopentanone

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine; sodium iodide / acetonitrile / 3.08 h / 0 °C / Inert atmosphere

2: 2-methyl-but-2-ene; 3-chloro-benzenecarboperoxoic acid / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 0 - 20 °C / Inert atmosphere

4: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 3.5 h / 30 °C / Inert atmosphere

With 2-methyl-but-2-ene; sodium hexamethyldisilazane; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;
DOI:10.1055/s-0033-1338573