(S)-3-{2-[(R)-1-((S)-1-Benzyloxy-propyl)-but-3-enyloxy]-acetyl}-4-isopropyl-oxazolidin-2-one

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Chemical Name:(S)-3-{2-[(R)-1-((S)-1-Benzyloxy-propyl)-but-3-enyloxy]-acetyl}-4-isopropyl-oxazolidin-2-one
CAS No.:600728-53-8
Molecular Formula:C₂₂H₃₁NO₅
Molecular Weight:389.492
Hs Code.:

Synonyms:(S)-3-{2-[(R)-1-((S)-1-Benzyloxy-propyl)-but-3-enyloxy]-acetyl}-4-isopropyl-oxazolidin-2-one

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Chemical Property of (S)-3-{2-[(R)-1-((S)-1-Benzyloxy-propyl)-but-3-enyloxy]-acetyl}-4-isopropyl-oxazolidin-2-one

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Technology Process of (S)-3-{2-[(R)-1-((S)-1-Benzyloxy-propyl)-but-3-enyloxy]-acetyl}-4-isopropyl-oxazolidin-2-one

There total 6 articles about (S)-3-{2-[(R)-1-((S)-1-Benzyloxy-propyl)-but-3-enyloxy]-acetyl}-4-isopropyl-oxazolidin-2-one 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: 70.0%

: 17016-83-0
(4S)-4-isopropyl-1,3-oxazolidin-2-one

: 600728-56-1
[(R)-1-((S)-1-Benzyloxy-propyl)-but-3-enyloxy]-acetic acid

: 600728-53-8
(S)-3-{2-[(R)-1-((S)-1-Benzyloxy-propyl)-but-3-enyloxy]-acetyl}-4-isopropyl-oxazolidin-2-one

Guidance literature:: [(R)-1-((S)-1-Benzyloxy-propyl)-but-3-enyloxy]-acetic acid; With pivaloyl chloride; triethylamine; In tetrahydrofuran; at -78 - 0 ℃;

(4S)-4-isopropyl-1,3-oxazolidin-2-one; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃;
DOI:10.1021/ol034923l

Reference yield:

: 924-41-4
1,5-hexadiene-3-ol

: 600728-53-8
(S)-3-{2-[(R)-1-((S)-1-Benzyloxy-propyl)-but-3-enyloxy]-acetyl}-4-isopropyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 16.25 g / (-)-dicyclohexyltartrate; titanium tetraisopropoxide; tert-butyl hydroperoxide / CH₂Cl₂ / 40 h / -20 °C

2.1: PPTS / 0 - 20 °C

2.2: 89 percent / CuI / tetrahydrofuran; diethyl ether / -30 °C

3.1: 94 percent / KH; Bu₄NI / tetrahydrofuran / 3 h / 0 - 20 °C

4.1: 91 percent / p-TsOH / methanol / 0 - 20 °C

5.1: NaH / tetrahydrofuran / 1 h / 0 °C

5.2: 98 percent / tetrahydrofuran / 84 h / 20 °C

6.1: pivaloyl chloride; Et₃N / tetrahydrofuran / -78 - 0 °C

6.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-dicyclohexyl D-tartrate; pyridinium p-toluenesulfonate; pivaloyl chloride; tetra-(n-butyl)ammonium iodide; potassium hydride; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1.1: Sharpless kinetic resolution;
DOI:10.1021/ol034923l

Reference yield:

: 99838-64-9
(4R,5S)-5-benzyloxy-1-hepten-4-ol

: 600728-53-8
(S)-3-{2-[(R)-1-((S)-1-Benzyloxy-propyl)-but-3-enyloxy]-acetyl}-4-isopropyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

1.2: 98 percent / tetrahydrofuran / 84 h / 20 °C

2.1: pivaloyl chloride; Et₃N / tetrahydrofuran / -78 - 0 °C

2.2: 70 percent / n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

With pivaloyl chloride; sodium hydride; triethylamine; In tetrahydrofuran;
DOI:10.1021/ol034923l