(3S,5S)-3-hydroxy-3-[(1S)-1-hydroxy-2-(phenylsulfanyl)ethyl]-5-isopropenyl-2,2-dimethylcyclohexanone

Base Information

Chemical Name:(3S,5S)-3-hydroxy-3-[(1S)-1-hydroxy-2-(phenylsulfanyl)ethyl]-5-isopropenyl-2,2-dimethylcyclohexanone
CAS No.:913093-77-3
Molecular Formula:C₁₉H₂₆O₃S
Molecular Weight:334.48
Hs Code.:

Synonyms:(3S,5S)-3-hydroxy-3-[(1S)-1-hydroxy-2-(phenylsulfanyl)ethyl]-5-isopropenyl-2,2-dimethylcyclohexanone

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Chemical Property of (3S,5S)-3-hydroxy-3-[(1S)-1-hydroxy-2-(phenylsulfanyl)ethyl]-5-isopropenyl-2,2-dimethylcyclohexanone

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Technology Process of (3S,5S)-3-hydroxy-3-[(1S)-1-hydroxy-2-(phenylsulfanyl)ethyl]-5-isopropenyl-2,2-dimethylcyclohexanone

There total 4 articles about (3S,5S)-3-hydroxy-3-[(1S)-1-hydroxy-2-(phenylsulfanyl)ethyl]-5-isopropenyl-2,2-dimethylcyclohexanone 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: 91.0%

: 913093-76-2
(3S,5S)-3-hydroxy-5-isopropenyl-2,2-dimethyl-3-[(2R)-oxiran-2-yl]cyclohexanone

: 108-98-5
thiophenol

: 913093-77-3
(3S,5S)-3-hydroxy-3-[(1S)-1-hydroxy-2-(phenylsulfanyl)ethyl]-5-isopropenyl-2,2-dimethylcyclohexanone

Guidance literature:: With potassium carbonate; In acetonitrile; for 2h;
DOI:10.1002/ejoc.200600284

Reference yield:

: 913093-74-0
(1R,3R,5R)-5-isopropenyl-2,2-dimethyl-1-vinylcyclohexane-1,3-diol

: 913093-77-3
(3S,5S)-3-hydroxy-3-[(1S)-1-hydroxy-2-(phenylsulfanyl)ethyl]-5-isopropenyl-2,2-dimethylcyclohexanone

Guidance literature:: Multi-step reaction with 3 steps

1: tert-butyl hydroperoxide / vanadylacetylacetonate / CH₂Cl₂

2: 9.5 g / CrO₃; aq. H₂SO₄ / acetone / 0.33 h / 0 °C

3: 91 percent / K₂CO₃ / acetonitrile / 2 h

With chromium(VI) oxide; tert.-butylhydroperoxide; sulfuric acid; potassium carbonate; bis(acetylacetonato) oxovanadium(IV); In dichloromethane; acetone; acetonitrile; 2: Jones oxidation;
DOI:10.1002/ejoc.200600284

Reference yield:

: 97643-04-4
2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone

: 913093-77-3
(3S,5S)-3-hydroxy-3-[(1S)-1-hydroxy-2-(phenylsulfanyl)ethyl]-5-isopropenyl-2,2-dimethylcyclohexanone

Guidance literature:: Multi-step reaction with 4 steps

1.1: BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 96 percent / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

2.1: tert-butyl hydroperoxide / vanadylacetylacetonate / CH₂Cl₂

3.1: 9.5 g / CrO₃; aq. H₂SO₄ / acetone / 0.33 h / 0 °C

4.1: 91 percent / K₂CO₃ / acetonitrile / 2 h

With chromium(VI) oxide; tert.-butylhydroperoxide; n-butyllithium; sulfuric acid; potassium carbonate; bis(acetylacetonato) oxovanadium(IV); In tetrahydrofuran; hexane; dichloromethane; acetone; acetonitrile; 3.1: Jones oxidation;
DOI:10.1002/ejoc.200600284