(4S,5S)-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]cyclohex-2-enone

Base Information

• Chemical Name: (4S,5S)-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]cyclohex-2-enone
• CAS No.: 518316-68-2
• Molecular Formula: C₁₅H₁₈O₄S
• Molecular Weight: 294.372
• Mol file: 518316-68-2.mol

Synonyms:(4S,5S)-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]cyclohex-2-enone

Chemical Property of (4S,5S)-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]cyclohex-2-enone

There total 4 articles about (4S,5S)-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]cyclohex-2-enone 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:

[4S,5S,SS]-4-hydroxy-5-methyl-4-[(p-tolylsulfinyl)methyl]-2-cyclohexen-1-one → (4S,5S)-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]cyclohex-2-enone (518316-68-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃;

DOI:10.1039/b209121f

Reference yield:

[(S)R]-4-hydroxy-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone (170117-33-6) → (4S,5S)-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]cyclohex-2-enone (518316-68-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / CH₂Cl₂; hexane / 4 h / -78 °C

2: 98 percent / meta-chloroperbenzoic acid / CH₂Cl₂ / 1 h / 0 °C

With 3-chloro-benzenecarboperoxoic acid; In hexane; dichloromethane;

DOI:10.1002/chem.200601330

Reference yield:

(R)-methyl p-tolyl sulfoxide (1519-39-7) → (4S,5S)-4-hydroxy-5-methyl-4-[(p-tolylsulfonyl)methyl]cyclohex-2-enone (518316-68-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran / -78 °C

1.2: oxalic acid / tetrahydrofuran; H₂O

2.1: 76 percent / CH₂Cl₂ / 4 h / -78 °C

3.1: MCPBA / CH₂Cl₂ / 0.5 h / 0 °C

With 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol050287a

upstream raw materials:

(R)-methyl p-tolyl sulfoxide

[(S)R]-4-hydroxy-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone

Downstream raw materials:

(4R,6S)-4-hydroxy-6-methylcyclohex-2-enone

(4R,6S)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-2-cyclohexenone

(1S,4R,6S)-4-[(tert-butyldimethylsilyl)oxy]-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-2-en-1-ol

(1S,4R,6S)-6-methyl-1-[(p-tolylsulfonyl)methyl]cyclohex-2-ene-1,4-diol