(4R)-4-benzyl-3-[(2S,3S)-2-benzyl-3-fluoropent-4-enoyl]-1,3-oxazolidin-2-one

Base Information

Chemical Name:(4R)-4-benzyl-3-[(2S,3S)-2-benzyl-3-fluoropent-4-enoyl]-1,3-oxazolidin-2-one
CAS No.:866994-28-7
Molecular Formula:C₂₂H₂₂FNO₃
Molecular Weight:367.42
Hs Code.:

Synonyms:(4R)-4-benzyl-3-[(2S,3S)-2-benzyl-3-fluoropent-4-enoyl]-1,3-oxazolidin-2-one

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Chemical Property of (4R)-4-benzyl-3-[(2S,3S)-2-benzyl-3-fluoropent-4-enoyl]-1,3-oxazolidin-2-one

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Technology Process of (4R)-4-benzyl-3-[(2S,3S)-2-benzyl-3-fluoropent-4-enoyl]-1,3-oxazolidin-2-one

There total 4 articles about (4R)-4-benzyl-3-[(2S,3S)-2-benzyl-3-fluoropent-4-enoyl]-1,3-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:

: 866994-20-9
(4R)-4-benzyl-3-[(2R,3E)-2-benzyl-5-(trimethylsilyl)pent-3-enoyl]-1,3-oxazolidin-2-one

: 866994-25-4
(4R)-4-benzyl-3-[(2S,3R)-2-benzyl-3-fluoropent-4-enoyl]-1,3-oxazolidin-2-one

: 866994-28-7
(4R)-4-benzyl-3-[(2S,3S)-2-benzyl-3-fluoropent-4-enoyl]-1,3-oxazolidin-2-one

Guidance literature:: With Selectfluor; In acetonitrile; at 20 ℃; for 48h;
DOI:10.1021/ol0518535

Reference yield:

: 866994-22-1
(4R)-4-benzyl-3-[(2R)-2-benzylbut-3-enoyl]-1,3-oxazolidin-2-one

: 866994-28-7
(4R)-4-benzyl-3-[(2S,3S)-2-benzyl-3-fluoropent-4-enoyl]-1,3-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / (Mes₂C₃H₅N₂)Cl₂Ru=CHPh / CH₂Cl₂ / 68 h

2: 1-ClCH₂-4-F-1,4-diazoniabicyclo[2.2.2]octane*2BF₄^(1-) / acetonitrile / 48 h / 20 °C

With (Mes₂C₃H₅N₂)Cl₂Ru=CHPh; Selectfluor; In dichloromethane; acetonitrile;
DOI:10.1021/ol0518535

Reference yield:

: 40217-17-2,90719-32-7,120574-96-1,102029-44-7
(R)-4-(phenylmethyl)-2-oxazolidinone

: 866994-28-7
(4R)-4-benzyl-3-[(2S,3S)-2-benzyl-3-fluoropent-4-enoyl]-1,3-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 77 percent / n-BuLi / tetrahydrofuran / 0.75 h / -78 - 0 °C

2.1: LDA; HMPA / tetrahydrofuran / 0.25 h / -78 °C

2.2: 56 percent / tetrahydrofuran / -78 - -10 °C

3.1: 95 percent / (Mes₂C₃H₅N₂)Cl₂Ru=CHPh / CH₂Cl₂ / 68 h

4.1: 1-ClCH₂-4-F-1,4-diazoniabicyclo[2.2.2]octane*2BF₄^(1-) / acetonitrile / 48 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; (Mes₂C₃H₅N₂)Cl₂Ru=CHPh; Selectfluor; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/ol0518535