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

Base Information

Chemical Name:(2S,3S,4S,5R)-2-hydroxy-3-isopropenyl-4-{[(p-methoxyphenyl)methoxy]methyl}-5-methylcyclopentanone
CAS No.:1621399-36-7
Molecular Formula:C₁₈H₂₄O₄
Molecular Weight:304.386
Hs Code.:

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

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

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

There total 6 articles about (2S,3S,4S,5R)-2-hydroxy-3-isopropenyl-4-{[(p-methoxyphenyl)methoxy]methyl}-5-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:

: 1621399-35-6
(3R,4S,5R)-3-isopropenyl-4-{[(p-methoxyphenyl)methoxy]methyl}-5-methyl-1-trimethylsiloxycyclopentene

: 1621399-36-7
(2S,3S,4S,5R)-2-hydroxy-3-isopropenyl-4-{[(p-methoxyphenyl)methoxy]methyl}-5-methylcyclopentanone

Guidance literature:: With 2-methyl-but-2-ene; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at 0 ℃; for 1.5h; Inert atmosphere;
DOI:10.1055/s-0033-1338573

Reference yield:

: 2-[(1S,2S,3R,4S)-2-{[(p-methoxyphenyl)methoxy]methyl}-3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl]prop-1-ene

: 1621399-36-7
(2S,3S,4S,5R)-2-hydroxy-3-isopropenyl-4-{[(p-methoxyphenyl)methoxy]methyl}-5-methylcyclopentanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridinium p-toluenesulfonate / methanol / 15 h

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

2.2: 1.75 h / 0 °C

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

4.1: 2-methyl-but-2-ene; 3-chloro-benzenecarboperoxoic acid / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

With 2-methyl-but-2-ene; oxalyl dichloride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; 2.1: |Swern Oxidation / 2.2: |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

: 1621399-36-7
(2S,3S,4S,5R)-2-hydroxy-3-isopropenyl-4-{[(p-methoxyphenyl)methoxy]methyl}-5-methylcyclopentanone

Guidance literature:: Multi-step reaction with 2 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

With 2-methyl-but-2-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; acetonitrile;
DOI:10.1055/s-0033-1338573