(4R)-4-benzyl-3-[(2R,3S)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]-oxazolidin-2-one

Base Information

Chemical Name:(4R)-4-benzyl-3-[(2R,3S)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]-oxazolidin-2-one
CAS No.:327165-41-3
Molecular Formula:C₂₅H₃₉NO₄Si
Molecular Weight:445.674
Hs Code.:

Synonyms:(4R)-4-benzyl-3-[(2R,3S)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]-oxazolidin-2-one

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Chemical Property of (4R)-4-benzyl-3-[(2R,3S)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]-oxazolidin-2-one

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Technology Process of (4R)-4-benzyl-3-[(2R,3S)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]-oxazolidin-2-one

There total 7 articles about (4R)-4-benzyl-3-[(2R,3S)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]-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: 97.0%

: 66-25-1
hexanal

: 327165-40-2
(R)-4-benzyl-3-[(E)-4-methyl-5-(trimethylsilanyl)pent-4-enoyl]oxazolidin-2-one

: 327165-41-3
(4R)-4-benzyl-3-[(2R,3S)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]-oxazolidin-2-one

Guidance literature:: With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃; for 3h;
DOI:10.1021/ol0069610

Reference yield:

: 66-25-1
hexanal

: 327165-40-2
(R)-4-benzyl-3-[(E)-4-methyl-5-(trimethylsilanyl)pent-4-enoyl]oxazolidin-2-one

: 327165-41-3
(4R)-4-benzyl-3-[(2R,3S)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]-oxazolidin-2-one

: (4R)-4-benzyl-3-[(2R,3R)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]oxazolidin-2-one

Guidance literature:: hexanal; (R)-4-benzyl-3-[(E)-4-methyl-5-(trimethylsilanyl)pent-4-enoyl]oxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃; for 3h;

With dihydrogen peroxide; In methanol; dichloromethane; at 20 ℃; for 1h; Title compound not separated from byproducts;
DOI:10.1021/ja048493l

Reference yield:

: 120417-01-8
<1-(acetyloxy)-2-methyl-2-propenyl>trimethylsilane

: 327165-41-3
(4R)-4-benzyl-3-[(2R,3S)-2-(2-methyl-3-trimethylsilyl-E-2-propen-1-yl)-3-hydroxyoctanoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: i-Pr₂NEt / CH₂Cl₂ / 72 h / 20 °C

2.1: aq. LiOH / methanol / 3 h / 0 - 23 °C

3.1: Et₃N / diethyl ether / 1 h / 23 °C

4.1: 1,10-phenanthroline; n-BuLi / tetrahydrofuran; hexane / -78 °C

4.2: 14.9 g / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 3 h / -78 - 0 °C

5.2: aq. H₂O₂ / methanol; CH₂Cl₂ / 1 h / 20 °C

With lithium hydroxide; n-butyllithium; 1,10-Phenanthroline; di-n-butylboryl trifluoromethanesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; 1.1: Ireland-Claisen rearrangement;
DOI:10.1021/ja048493l