(2S,3R)-2-(tert-butyldimethylsilyloxy)-3-[(2-methoxyethoxy)methoxy]-1-[(R)-p-tolylsulfinyl]hex-5-ene

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Chemical Name:(2S,3R)-2-(tert-butyldimethylsilyloxy)-3-[(2-methoxyethoxy)methoxy]-1-[(R)-p-tolylsulfinyl]hex-5-ene
CAS No.:852637-88-8
Molecular Formula:C₂₃H₄₀O₅SSi
Molecular Weight:456.719
Hs Code.:

Synonyms:(2S,3R)-2-(tert-butyldimethylsilyloxy)-3-[(2-methoxyethoxy)methoxy]-1-[(R)-p-tolylsulfinyl]hex-5-ene

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Chemical Property of (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-[(2-methoxyethoxy)methoxy]-1-[(R)-p-tolylsulfinyl]hex-5-ene

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Technology Process of (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-[(2-methoxyethoxy)methoxy]-1-[(R)-p-tolylsulfinyl]hex-5-ene

There total 6 articles about (2S,3R)-2-(tert-butyldimethylsilyloxy)-3-[(2-methoxyethoxy)methoxy]-1-[(R)-p-tolylsulfinyl]hex-5-ene 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: 77.0%

: 3970-21-6
2-Methoxyethoxymethyl chloride

: 221638-09-1
(2S,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-toluene-4-sulfinyl)-hex-5-en-3-ol

: 852637-88-8
(2S,3R)-2-(tert-butyldimethylsilyloxy)-3-[(2-methoxyethoxy)methoxy]-1-[(R)-p-tolylsulfinyl]hex-5-ene

Guidance literature:: With potassium hydride; In tetrahydrofuran; at -78 - 20 ℃; for 1.75h;
DOI:10.1016/j.tetasy.2005.01.050

Reference yield:

: 1519-39-7
(R)-methyl p-tolyl sulfoxide

: 852637-88-8
(2S,3R)-2-(tert-butyldimethylsilyloxy)-3-[(2-methoxyethoxy)methoxy]-1-[(R)-p-tolylsulfinyl]hex-5-ene

Guidance literature:: Multi-step reaction with 6 steps

1.1: BuLi; cyclohexylisopropylamine / tetrahydrofuran; hexane / -78 - -40 °C

1.2: 70 percent / tetrahydrofuran; hexane

2.1: 80 percent / Dibal-H / tetrahydrofuran; toluene / 0.5 h / -78 °C

3.1: 84 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 2 h

4.1: tetrahydrofuran; diethyl ether / 1 h

5.1: 0.802 g / ZnI₂; Dibal-H / tetrahydrofuran; hexane / 0.33 h / -78 °C

6.1: 77 percent / KH / tetrahydrofuran / 1.75 h / -78 - 20 °C

With n-butyllithium; N-cyclohexylisopropylamine; potassium hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; zinc(II) iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1016/j.tetasy.2005.01.050

Reference yield:

: 196409-50-4
(S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-((R)-toluene-4-sulfinyl)-hex-5-en-3-one

: 852637-88-8
(2S,3R)-2-(tert-butyldimethylsilyloxy)-3-[(2-methoxyethoxy)methoxy]-1-[(R)-p-tolylsulfinyl]hex-5-ene

Guidance literature:: Multi-step reaction with 2 steps

1: 0.802 g / ZnI₂; Dibal-H / tetrahydrofuran; hexane / 0.33 h / -78 °C

2: 77 percent / KH / tetrahydrofuran / 1.75 h / -78 - 20 °C

With potassium hydride; diisobutylaluminium hydride; zinc(II) iodide; In tetrahydrofuran; hexane;
DOI:10.1016/j.tetasy.2005.01.050