(δS,4R,5R)-δ-chloro-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-pentanenitrile

Base Information

Chemical Name:(δS,4R,5R)-δ-chloro-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-pentanenitrile
CAS No.:238088-24-9
Molecular Formula:C₂₇H₄₉BClNO₃Si
Molecular Weight:510.04
Hs Code.:

Synonyms:(δS,4R,5R)-δ-chloro-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-pentanenitrile

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Chemical Property of (δS,4R,5R)-δ-chloro-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-pentanenitrile

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Technology Process of (δS,4R,5R)-δ-chloro-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-pentanenitrile

There total 4 articles about (δS,4R,5R)-δ-chloro-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-pentanenitrile 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%

: 238088-21-6
(4R,5R)-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-butanenitrile

: 75-09-2
dichloromethane

: 238088-24-9
(δS,4R,5R)-δ-chloro-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-pentanenitrile

Guidance literature:: dichloromethane; With n-butyllithium; In tetrahydrofuran; at -100 ℃;

(4R,5R)-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-butanenitrile; In tetrahydrofuran; at -100 - -78 ℃; for 0.75h;

With zinc(II) chloride; In tetrahydrofuran; at 20 - 25 ℃; for 18h; Further stages.;
DOI:10.1021/ol990579+

Reference yield:

: 101166-65-8
2-tert-butyldimethylsilyloxyethyl iodide

: 238088-24-9
(δS,4R,5R)-δ-chloro-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-pentanenitrile

Guidance literature:: Multi-step reaction with 2 steps

1.1: LDA / cyclohexane; tetrahydrofuran / 0.67 h / -78 °C

1.2: 97 percent / cyclohexane; tetrahydrofuran / 15 h / 20 - 25 °C

2.1: BuLi / tetrahydrofuran / -100 °C

2.2: tetrahydrofuran / 0.75 h / -100 - -78 °C

2.3: 91 percent / ZnCl₂ / tetrahydrofuran / 18 h / 20 - 25 °C

With n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; cyclohexane;
DOI:10.1021/ol990579+

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 238088-24-9
(δS,4R,5R)-δ-chloro-4,5-dicyclohexyl-α-[2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1,3,2-dioxaborolane-2-pentanenitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: 76 percent / LDA / tetrahydrofuran; cyclohexane / 15 h / 20 - 25 °C

2.1: LDA / cyclohexane; tetrahydrofuran / 0.67 h / -78 °C

2.2: 97 percent / cyclohexane; tetrahydrofuran / 15 h / 20 - 25 °C

3.1: BuLi / tetrahydrofuran / -100 °C

3.2: tetrahydrofuran / 0.75 h / -100 - -78 °C

3.3: 91 percent / ZnCl₂ / tetrahydrofuran / 18 h / 20 - 25 °C

With n-butyllithium; lithium diisopropyl amide; In tetrahydrofuran; cyclohexane;
DOI:10.1021/ol990579+