[4R,5R,SS]-4-hydroxy-5-methyl-4-[(p-tolylsulfinyl)methyl]-2-cyclohexen-1-one

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Chemical Name:[4R,5R,SS]-4-hydroxy-5-methyl-4-[(p-tolylsulfinyl)methyl]-2-cyclohexen-1-one
CAS No.:473536-53-7
Molecular Formula:C₁₅H₁₈O₃S
Molecular Weight:278.372
Hs Code.:

Synonyms:[4R,5R,SS]-4-hydroxy-5-methyl-4-[(p-tolylsulfinyl)methyl]-2-cyclohexen-1-one

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Chemical Property of [4R,5R,SS]-4-hydroxy-5-methyl-4-[(p-tolylsulfinyl)methyl]-2-cyclohexen-1-one

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Technology Process of [4R,5R,SS]-4-hydroxy-5-methyl-4-[(p-tolylsulfinyl)methyl]-2-cyclohexen-1-one

There total 4 articles about [4R,5R,SS]-4-hydroxy-5-methyl-4-[(p-tolylsulfinyl)methyl]-2-cyclohexen-1-one 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: 65.0%

: 75-24-1
trimethylaluminum

: 473536-52-6
(SS)-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-cyclohexa-2,5-dienone

: 473536-53-7
[4R,5R,SS]-4-hydroxy-5-methyl-4-[(p-tolylsulfinyl)methyl]-2-cyclohexen-1-one

Guidance literature:: In dichloromethane; at -78 ℃; for 4h;
DOI:10.1002/1521-3773(20020802)41:15<2755::AID-ANIE2755>3.0.CO;2-A DOI:10.1021/ol050287a

Reference yield:

: 5056-07-5
(S)-methyl p-tolyl sulfoxide

: 473536-53-7
[4R,5R,SS]-4-hydroxy-5-methyl-4-[(p-tolylsulfinyl)methyl]-2-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi; diisopropylamine / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: hexane; tetrahydrofuran / 2 h / -78 °C

1.3: 76 percent / oxalic acid / H₂O; tetrahydrofuran / 2 h

2.1: 65 percent / CH₂Cl₂; heptane / 4 h / -78 °C

With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; n-heptane; dichloromethane;
DOI:10.1002/chem.200600809

Reference yield:

: (S)-(-)-Lithium methyl p-tolyl sulphoxide

: 473536-53-7
[4R,5R,SS]-4-hydroxy-5-methyl-4-[(p-tolylsulfinyl)methyl]-2-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.2: aqueous oxalic acid

2.1: 65 percent / CH₂Cl₂ / 4 h / -78 °C

In dichloromethane;
DOI:10.1002/1521-3773(20020802)41:15<2755::AID-ANIE2755>3.0.CO;2-A