[2S,6R,(S)R]-2-(p-methoxyphenyl)-6-[(p-tolylsulfinyl)methyl]tetrahydropyran

Base Information

Chemical Name:[2S,6R,(S)R]-2-(p-methoxyphenyl)-6-[(p-tolylsulfinyl)methyl]tetrahydropyran
CAS No.:436807-64-6
Molecular Formula:C₂₀H₂₄O₃S
Molecular Weight:344.475
Hs Code.:

Synonyms:[2S,6R,(S)R]-2-(p-methoxyphenyl)-6-[(p-tolylsulfinyl)methyl]tetrahydropyran

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Chemical Property of [2S,6R,(S)R]-2-(p-methoxyphenyl)-6-[(p-tolylsulfinyl)methyl]tetrahydropyran

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Technology Process of [2S,6R,(S)R]-2-(p-methoxyphenyl)-6-[(p-tolylsulfinyl)methyl]tetrahydropyran

There total 6 articles about [2S,6R,(S)R]-2-(p-methoxyphenyl)-6-[(p-tolylsulfinyl)methyl]tetrahydropyran 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: 92.0%

: 436807-30-6
[5R,(S)R]-5-hydroxy-1-(p-methoxyphenyl)-6-(p-tolylsulfinyl)hexanone

: 436807-64-6
[2S,6R,(S)R]-2-(p-methoxyphenyl)-6-[(p-tolylsulfinyl)methyl]tetrahydropyran

Guidance literature:: With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.25h;
DOI:10.1021/jo034817x

Reference yield:

: 1519-39-7
(R)-methyl p-tolyl sulfoxide

: 436807-64-6
[2S,6R,(S)R]-2-(p-methoxyphenyl)-6-[(p-tolylsulfinyl)methyl]tetrahydropyran

Guidance literature:: Multi-step reaction with 6 steps

1: LDA / tetrahydrofuran / 2 h / -78 °C

2: K₂CO₃ / acetone / 2 h / Heating

3: 87 percent / DIBALH; ZnBr₂ / tetrahydrofuran; heptane / 0.5 h / -78 °C

4: 93 percent / AlMe₃ / CH₂Cl₂ / 4 h / Heating

5: 71 percent / tetrahydrofuran; diethyl ether / 50 °C

6: 92 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.25 h / 0 °C

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; trimethylaluminum; diisobutylaluminium hydride; potassium carbonate; zinc dibromide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; n-heptane; dichloromethane; acetone;
DOI:10.1021/jo034817x

Reference yield:

: 133043-02-4
(+)-methyl <(S)R>-5-oxo-6-(p-tolylsulfinyl)hexanoate

: 436807-64-6
[2S,6R,(S)R]-2-(p-methoxyphenyl)-6-[(p-tolylsulfinyl)methyl]tetrahydropyran

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / DIBALH; ZnBr₂ / tetrahydrofuran; heptane / 0.5 h / -78 °C

2: 93 percent / AlMe₃ / CH₂Cl₂ / 4 h / Heating

3: 71 percent / tetrahydrofuran; diethyl ether / 50 °C

4: 92 percent / Et₃SiH; TMSOTf / CH₂Cl₂ / 0.25 h / 0 °C

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; trimethylaluminum; diisobutylaluminium hydride; zinc dibromide; In tetrahydrofuran; diethyl ether; n-heptane; dichloromethane;
DOI:10.1021/jo034817x