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

Base Information

Chemical Name:(3S,5S)-3-hydroxy-5-isopropenyl-2,2-dimethyl-3-[(2R)-oxiran-2-yl]cyclohexanone
CAS No.:913093-76-2
Molecular Formula:C₁₃H₂₀O₃
Molecular Weight:224.3
Hs Code.:

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

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Chemical Property of (3S,5S)-3-hydroxy-5-isopropenyl-2,2-dimethyl-3-[(2R)-oxiran-2-yl]cyclohexanone

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Technology Process of (3S,5S)-3-hydroxy-5-isopropenyl-2,2-dimethyl-3-[(2R)-oxiran-2-yl]cyclohexanone

There total 3 articles about (3S,5S)-3-hydroxy-5-isopropenyl-2,2-dimethyl-3-[(2R)-oxiran-2-yl]cyclohexanone 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:

: (1S,3R,5R)-5-Isopropenyl-2,2-dimethyl-1-(R)-oxiranyl-cyclohexane-1,3-diol

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

Guidance literature:: With chromium(VI) oxide; sulfuric acid; In acetone; at 0 ℃; for 0.333333h;
DOI:10.1002/ejoc.200600284

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 steps

1: tert-butyl hydroperoxide / vanadylacetylacetonate / CH₂Cl₂

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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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