(E)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol

Base Information

Chemical Name:(E)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol
CAS No.:1246364-52-2
Molecular Formula:C₁₅H₂₈O₂Si
Molecular Weight:268.472
Hs Code.:

Synonyms:(E)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol

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Chemical Property of (E)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol

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Technology Process of (E)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol

There total 2 articles about (E)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol 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:

: 1279708-92-7
[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene] acetic acid methyl ester

: 1246364-53-3
(Z)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol

: 1246364-52-2
(E)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane;
DOI:10.1016/j.jsbmb.2010.03.063

Reference yield:

: 4746-97-8
cyclohexanedione monoethylene ketal

: 1246364-53-3
(Z)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol

: 1246364-52-2
(E)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: L-proline; Nitrosobenzene / chloroform / 26 h / 4 - 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C

3.1: n-butyllithium / hexane; tetrahydrofuran / 0 - 20 °C

3.2: 5 h / -78 - 20 °C

4.1: iron(III) chloride hexahydrate / dichloromethane / 20 °C

5.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

5.2: 2 h / -78 °C

6.1: diisobutylaluminium hydride / dichloromethane / 3 h / -70 - -40 °C

6.3: Resolution of racemate

With 1H-imidazole; n-butyllithium; iron(III) chloride hexahydrate; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; Nitrosobenzene; L-proline; In tetrahydrofuran; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; 3.1: Wittig Reaction / 5.1: Peterson reaction;

Reference yield: 69.0%

: 1246364-52-2
(E)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol

: 829-85-6
diphenylphosphane

: 1246364-54-4
[(E)-[(3'R)-[(tert-butyldimethylsilyl)oxy]-4'-methylenecyclohexylidene]ethyl]diphenylphosphine oxide

Guidance literature:: (E)-2-[(R)-3'-[(tert-butyldimethylsilyl)oxy]-4'-methylene-cyclohexylidene]ethanol; With n-butyllithium; p-toluenesulfonyl chloride; In tetrahydrofuran; hexane; at 0 ℃; Inert atmosphere;

diphenylphosphane; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; Inert atmosphere;

With dihydrogen peroxide; In dichloromethane; water; at 0 ℃; for 1h;