(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile

Base Information

Chemical Name:(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile
CAS No.:937067-97-5
Molecular Formula:C₂₄H₃₁NO₂Si
Molecular Weight:393.601
Hs Code.:

Synonyms:(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile

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Chemical Property of (3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile

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Technology Process of (3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile

There total 4 articles about (3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile 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: 52.0%

: 107-12-0
propiononitrile

: 937067-95-3
tert-butyldiphenyl(((2S,3S)-3-ethenyloxiran-2-yl)methoxy)silane

: 937067-97-5
(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile

Guidance literature:: propiononitrile; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

tert-butyldiphenyl(((2S,3S)-3-ethenyloxiran-2-yl)methoxy)silane; In tetrahydrofuran; at -78 - -10 ℃; for 2h; Further stages.;
DOI:10.1021/jo0626461

Reference yield:

: 92808-78-1
(E)-4-(tert-butyldiphenylsilyloxy)-2-buten-1-ol

: 937067-97-5
(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile

Guidance literature:: Multi-step reaction with 4 steps

1.1: (+)-diethyl L-tartrate; titanium(IV) isopropoxide / CH₂Cl₂ / 0.33 h / -30 - -20 °C

1.2: tert-butyl hydroperoxide / CH₂Cl₂ / 5.5 h / -30 - -20 °C

2.1: Dess-Martin reagent / CH₂Cl₂ / 2.5 h / 20 °C

3.1: KOtBu / tetrahydrofuran / 0.5 h / 0 °C

3.2: 14.0 g / tetrahydrofuran / 2 h / 20 °C

4.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

4.2: 52 percent / tetrahydrofuran / 2 h / -78 - -10 °C

With titanium(IV) isopropylate; n-butyllithium; diethyl (2R,3R)-tartrate; potassium tert-butylate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo0626461

Reference yield:

: 131484-40-7
((2S,3S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)oxiran-2-yl)methanol

: 937067-97-5
(3S)-3-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2-methyl-4-pentenenitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: Dess-Martin reagent / CH₂Cl₂ / 2.5 h / 20 °C

2.1: KOtBu / tetrahydrofuran / 0.5 h / 0 °C

2.2: 14.0 g / tetrahydrofuran / 2 h / 20 °C

3.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C

3.2: 52 percent / tetrahydrofuran / 2 h / -78 - -10 °C

With n-butyllithium; potassium tert-butylate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo0626461