(Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane

Base Information

Chemical Name:(Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane
CAS No.:216380-59-5
Molecular Formula:C₂₁H₄₁ClO₂Si₂
Molecular Weight:417.179
Hs Code.:

Synonyms:(Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane

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Chemical Property of (Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane

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Technology Process of (Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane

There total 2 articles about (Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane 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%

: 215929-41-2
(Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

: 216380-59-5
(Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane

Guidance literature:: With N-chloro-succinimide; dimethylsulfide; In dichloromethane; at -20 - 20 ℃;
DOI:10.1016/S0968-0896(00)00259-5

Reference yield:

: methyl (Z,3S,5RS)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]acetate

: 216380-59-5
(Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane

Guidance literature:: Multi-step reaction with 2 steps

1: 40 percent / DIBAL / toluene; CH₂Cl₂ / 0.5 h / -78 °C

2: 91 percent / N-chlorosuccinimide; dimethyl sulfide / CH₂Cl₂ / -20 - 20 °C

With N-chloro-succinimide; dimethylsulfide; diisobutylaluminium hydride; In dichloromethane; toluene; 2: chlorination;
DOI:10.1016/S0968-0896(00)00259-5

Reference yield:

: 216380-59-5
(Z,3S,5S)-2-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]-1-chloroethane

: 3-Epi-1alpha,25-dihydroxy-22-oxavitamin D₃

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -50 °C

1.2: 72 percent / aq. H₂O₂ / CHCl₃; tetrahydrofuran / 1.5 h / 20 °C

2.1: 45 percent / n-BuLi / tetrahydrofuran; hexane / 6 h / -78 °C

3.1: 100 percent / TBAF / tetrahydrofuran / 18 h / 20 °C

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; 1.2: oxidation;
DOI:10.1016/S0968-0896(00)00259-5