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

Base Information

• Chemical Name: (2S,3S,4S,5R)-3-isopropenyl-2-methoxymethoxy-4-{[(p-methoxyphenyl)methoxy]methyl}-5-methylcyclopentanone
• CAS No.: 1621399-37-8
• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.439

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (2S,3S,4S,5R)-3-isopropenyl-2-methoxymethoxy-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: 95.0%

(2S,3S,4S,5R)-2-hydroxy-3-isopropenyl-4-{[(p-methoxyphenyl)methoxy]methyl}-5-methylcyclopentanone (1621399-36-7) + chloromethyl methyl ether (107-30-2) → (2S,3S,4S,5R)-3-isopropenyl-2-methoxymethoxy-4-{[(p-methoxyphenyl)methoxy]methyl}-5-methylcyclopentanone (1621399-37-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 15h; Inert atmosphere;

DOI:10.1055/s-0033-1338573

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (2S,3S,4S,5R)-3-isopropenyl-2-methoxymethoxy-4-{[(p-methoxyphenyl)methoxy]methyl}-5-methylcyclopentanone (1621399-37-8)

Guidance literature:

Multi-step reaction with 6 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

With 2-methyl-but-2-ene; oxalyl dichloride; 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; acetonitrile; mineral oil; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;

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

Guidance literature:

Multi-step reaction with 5 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

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

With 2-methyl-but-2-ene; oxalyl dichloride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 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

upstream raw materials:

p-methoxybenzyl chloride

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

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

chloromethyl methyl ether

Downstream raw materials:

(2R,3S,4S,5S)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-isopropenyl-5-methoxymethoxy-3-{[(p-methoxyphenyl)methoxy]methyl}-2-methylcyclopentanone

(2R,3S,4S,5R)-2-[(2E)-3,7-dimethyl-2,6-octadienyl]-4-isopropenyl-5-methoxymethoxy-3-{[(p-methoxyphenyl)methoxy]methyl}-2-methylcyclopentanone

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

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

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