(1S,2S,3S,4R)-3-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol

Base Information

Chemical Name:(1S,2S,3S,4R)-3-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol
CAS No.:1431536-56-9
Molecular Formula:C₂₀H₃₃BrO₃
Molecular Weight:401.384
Hs Code.:

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

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

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

There total 13 articles about (1S,2S,3S,4R)-3-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol 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: 83.0%

: 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

: 1431536-56-9
(1S,2S,3S,4R)-3-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 - 20 ℃; stereoselective reaction;
DOI:10.1021/ol400754e

Reference yield:

: 1431302-69-0
(((1R,2S,4S)-2-bromo-4-(3-chloroprop-1-en-2-yl)-1-methylcyclohexyl)oxy)(isopropyl)dimethylsilane

: 1431536-56-9
(1S,2S,3S,4R)-3-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium iodide / acetone / 20 °C

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

2.2: -78 - 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

4.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0 - 20 °C

With sodium tetrahydroborate; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium iodide; In tetrahydrofuran; methanol; acetone; toluene; 1.1: |Finkelstein Reaction;
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

: 1431536-56-9
(1S,2S,3S,4R)-3-(2-((1S,3S,4R)-3-bromo-4-hydroxy-4-methylcyclohexyl)allyl)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol

Guidance literature:: Multi-step reaction with 3 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

3.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0 - 20 °C

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