(2R,3S)-2,2-dimethyl-propionic acid 3-(dimethyl-phenyl-silanyl)-2-hydroxy-pent-4-enyl ester

Base Information

Chemical Name:(2R,3S)-2,2-dimethyl-propionic acid 3-(dimethyl-phenyl-silanyl)-2-hydroxy-pent-4-enyl ester
CAS No.:757749-62-5
Molecular Formula:C₁₈H₂₈O₃Si
Molecular Weight:320.504
Hs Code.:

Synonyms:(2R,3S)-2,2-dimethyl-propionic acid 3-(dimethyl-phenyl-silanyl)-2-hydroxy-pent-4-enyl ester

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Chemical Property of (2R,3S)-2,2-dimethyl-propionic acid 3-(dimethyl-phenyl-silanyl)-2-hydroxy-pent-4-enyl ester

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Technology Process of (2R,3S)-2,2-dimethyl-propionic acid 3-(dimethyl-phenyl-silanyl)-2-hydroxy-pent-4-enyl ester

There total 4 articles about (2R,3S)-2,2-dimethyl-propionic acid 3-(dimethyl-phenyl-silanyl)-2-hydroxy-pent-4-enyl ester 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: 56.0%

: 18001-18-8
allyldimethylphenylsilane

: 72117-30-7
2,2-dimethylpropionic acid 2-oxoethyl ester

: 757749-62-5
(2R,3S)-2,2-dimethyl-propionic acid 3-(dimethyl-phenyl-silanyl)-2-hydroxy-pent-4-enyl ester

Guidance literature:: allyldimethylphenylsilane; With n-butyllithium; In tetrahydrofuran; at 20 ℃; for 0.333333h;

With (R,R)-taddol(cyclopentadienyl)TiCl; In tetrahydrofuran; at -78 ℃; for 0.5h;

2,2-dimethylpropionic acid 2-oxoethyl ester; In tetrahydrofuran; at -78 ℃; for 3h; Further stages.;
DOI:10.1016/j.tet.2004.05.058

Reference yield:

: 62244-21-7
(2,2-dimethyl-1,3-dioxolane-4-yl)methyl pivalate

: 757749-62-5
(2R,3S)-2,2-dimethyl-propionic acid 3-(dimethyl-phenyl-silanyl)-2-hydroxy-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 98 percent / aq. HCl / tetrahydrofuran

2.1: 71 percent / NaIO₄ / CH₂Cl₂; H₂O / 4 h / 20 °C

3.1: n-BuLi / tetrahydrofuran / 0.33 h / 20 °C

3.2: (R,R)-TiClCpTADDOL / tetrahydrofuran / 0.5 h / -78 °C

3.3: 56 percent / tetrahydrofuran / 3 h / -78 °C

With hydrogenchloride; sodium periodate; n-butyllithium; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tet.2004.05.058

Reference yield:

: 3282-30-2
pivaloyl chloride

: 757749-62-5
(2R,3S)-2,2-dimethyl-propionic acid 3-(dimethyl-phenyl-silanyl)-2-hydroxy-pent-4-enyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 83 percent / pyridine / CH₂Cl₂ / 48 h / 20 °C

2.1: 98 percent / aq. HCl / tetrahydrofuran

3.1: 71 percent / NaIO₄ / CH₂Cl₂; H₂O / 4 h / 20 °C

4.1: n-BuLi / tetrahydrofuran / 0.33 h / 20 °C

4.2: (R,R)-TiClCpTADDOL / tetrahydrofuran / 0.5 h / -78 °C

4.3: 56 percent / tetrahydrofuran / 3 h / -78 °C

With pyridine; hydrogenchloride; sodium periodate; n-butyllithium; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tet.2004.05.058