(2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone

Base Information

Chemical Name:(2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone
CAS No.:1431302-63-4
Molecular Formula:C₂₀H₃₁BrO₃
Molecular Weight:399.368
Hs Code.:

Synonyms:(2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone

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Chemical Property of (2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone

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Technology Process of (2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone

There total 12 articles about (2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-2-hydroxy-2-methyl-5-(prop-1-en-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: 51.0%

: 1431302-70-3
(2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-((isopropyldimethylsilyl)oxy)-4-methylcyclohexyl)allyl)-2-((tert-butyldimethylsilyl)oxy)-2-methyl-5-(prop-1-en-2-yl)cyclohexanone

: 1431302-63-4
(2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol400754e

Reference yield:

: 1431302-64-5
(((1R,2S,4S)-2-bromo-4-(3-iodoprop-1-en-2-yl)-1-methylcyclohexyl)oxy)(isopropyl)dimethylsilane

: 1431302-63-4
(2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C

1.2: -78 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

With tetrabutyl ammonium fluoride; potassium hexamethylsilazane; In tetrahydrofuran; toluene;
DOI:10.1021/ol400754e

Reference yield:

: 203719-53-3
(-)-limonene oxide

: 1431302-63-4
(2S,5R,6S)-6-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone

Guidance literature:: Multi-step reaction with 10 steps

1.1: potassium phosphate / aq. phosphate buffer / 32 h / 20 °C / pH 3.1

2.1: 2-iodoxybenzoic acid / ethyl acetate / 16 h / Reflux

3.1: 2,6-dimethylpyridine / dichloromethane / -78 - 20 °C / Inert atmosphere

4.1: methanol / 5 h / 20 °C

5.1: n-butyllithium; copper(ll) bromide / tetrahydrofuran; hexane; tert-butyl alcohol / 0 - 20 °C / Inert atmosphere

6.1: 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane / benzene / 1 h / Reflux

7.1: cerium(III) chloride heptahydrate; sodium hypochlorite / dichloromethane; water / 2 h / 0 - 20 °C

8.1: sodium iodide / acetone / 20 °C

9.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 °C

9.2: -78 - 20 °C

10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

With 2,6-dimethylpyridine; sodium hypochlorite; potassium phosphate; n-butyllithium; 2-iodoxybenzoic acid; 2,2'-azobis(isobutyronitrile); cerium(III) chloride heptahydrate; tris-(trimethylsilyl)silane; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium iodide; copper(ll) bromide; In tetrahydrofuran; methanol; aq. phosphate buffer; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; tert-butyl alcohol; benzene; 8.1: |Finkelstein Reaction;
DOI:10.1021/ol400754e