(2R,3S)-3-hydroxy-2-(2-methylpropyl)-3-(2-naphthyl)-2-phenylpropanenitrile

Base Information

Chemical Name:(2R,3S)-3-hydroxy-2-(2-methylpropyl)-3-(2-naphthyl)-2-phenylpropanenitrile
CAS No.:960595-26-0
Molecular Formula:C₂₃H₂₃NO
Molecular Weight:329.442
Hs Code.:

Synonyms:(2R,3S)-3-hydroxy-2-(2-methylpropyl)-3-(2-naphthyl)-2-phenylpropanenitrile

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Chemical Property of (2R,3S)-3-hydroxy-2-(2-methylpropyl)-3-(2-naphthyl)-2-phenylpropanenitrile

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Technology Process of (2R,3S)-3-hydroxy-2-(2-methylpropyl)-3-(2-naphthyl)-2-phenylpropanenitrile

There total 3 articles about (2R,3S)-3-hydroxy-2-(2-methylpropyl)-3-(2-naphthyl)-2-phenylpropanenitrile 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: 90.0%

: 849518-86-1
1-(1,1-dimethylethyl)-1,1-dimethyl-N-(4-methyl-2-phenyl-1-pentenylidene)silanamine

: 66-99-9
β-naphthaldehyde

: 960595-26-0
(2R,3S)-3-hydroxy-2-(2-methylpropyl)-3-(2-naphthyl)-2-phenylpropanenitrile

: C₂₃H₂₃NO

Guidance literature:: 1-(1,1-dimethylethyl)-1,1-dimethyl-N-(4-methyl-2-phenyl-1-pentenylidene)silanamine; β-naphthaldehyde; With tetrachlorosilane; chiral bisphosphoramide catalyst; In dichloromethane; at -78 ℃; for 2h; Further stages.;
DOI:10.1021/ja077134y

Reference yield: 90.0%

: 849518-86-1
1-(1,1-dimethylethyl)-1,1-dimethyl-N-(4-methyl-2-phenyl-1-pentenylidene)silanamine

: 66-99-9
β-naphthaldehyde

: 960595-26-0
(2R,3S)-3-hydroxy-2-(2-methylpropyl)-3-(2-naphthyl)-2-phenylpropanenitrile

Guidance literature:: β-naphthaldehyde; With tetrachlorosilane; Denmark's dimeric catalyst; In dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere; Schlenk technique;

1-(1,1-dimethylethyl)-1,1-dimethyl-N-(4-methyl-2-phenyl-1-pentenylidene)silanamine; In dichloromethane; at -78 ℃; for 2.08333h; stereoselective reaction; Inert atmosphere; Schlenk technique;
DOI:10.1002/chem.201403342

Reference yield:

: 5558-31-6
4-methyl-2-phenylpentanenitrile

: 960595-26-0
(2R,3S)-3-hydroxy-2-(2-methylpropyl)-3-(2-naphthyl)-2-phenylpropanenitrile

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium; diisopropylamine / hexane; tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere; Schlenk technique

1.2: 1 h / -78 - 20 °C / Inert atmosphere; Schlenk technique

2.1: Denmark's dimeric catalyst; tetrachlorosilane / dichloromethane / 0.08 h / -78 °C / Inert atmosphere; Schlenk technique

2.2: 2.08 h / -78 °C / Inert atmosphere; Schlenk technique

With n-butyllithium; tetrachlorosilane; Denmark's dimeric catalyst; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1002/chem.201403342