4-(S)-benzyl-3-[2-(R)-(1-tert-butyldimethylsilyloxy-2-cyclopenten-2-yl)-methyl]-butyryl-2-oxazolidinone

Base Information

Chemical Name:4-(S)-benzyl-3-[2-(R)-(1-tert-butyldimethylsilyloxy-2-cyclopenten-2-yl)-methyl]-butyryl-2-oxazolidinone
CAS No.:371115-19-4
Molecular Formula:C₂₆H₃₉NO₄Si
Molecular Weight:457.685
Hs Code.:

Synonyms:4-(S)-benzyl-3-[2-(R)-(1-tert-butyldimethylsilyloxy-2-cyclopenten-2-yl)-methyl]-butyryl-2-oxazolidinone

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Chemical Property of 4-(S)-benzyl-3-[2-(R)-(1-tert-butyldimethylsilyloxy-2-cyclopenten-2-yl)-methyl]-butyryl-2-oxazolidinone

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Technology Process of 4-(S)-benzyl-3-[2-(R)-(1-tert-butyldimethylsilyloxy-2-cyclopenten-2-yl)-methyl]-butyryl-2-oxazolidinone

There total 5 articles about 4-(S)-benzyl-3-[2-(R)-(1-tert-butyldimethylsilyloxy-2-cyclopenten-2-yl)-methyl]-butyryl-2-oxazolidinone 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: 94.0%

: 111292-87-6,143097-11-4,112459-79-7
(S)-4-benzyl-3-butyryloxazolidin-2-one

: 371115-18-3
1-iodomethyl-5-tert-butyldimethylsilyloxy-cyclopent-1-ene

: 371115-19-4
4-(S)-benzyl-3-[2-(R)-(1-tert-butyldimethylsilyloxy-2-cyclopenten-2-yl)-methyl]-butyryl-2-oxazolidinone

Guidance literature:: (S)-4-benzyl-3-butyryloxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

1-iodomethyl-5-tert-butyldimethylsilyloxy-cyclopent-1-ene; In tetrahydrofuran; at -78 ℃; for 4h; Further stages.;
DOI:10.1021/ol0165037

Reference yield:

: 115401-40-6
ethyl (±)-5-hydroxycyclopent-1-enecarboxylate

: 371115-19-4
4-(S)-benzyl-3-[2-(R)-(1-tert-butyldimethylsilyloxy-2-cyclopenten-2-yl)-methyl]-butyryl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 4 steps

1.1: 87 percent / imidazole / dimethylformamide / 4 h / 20 °C

2.1: 77 percent / DIBAL-H / toluene; CH₂Cl₂ / 5 h / -70 °C

3.1: 69 percent / EtOOCN=NCOOEt; Ph₃P; ZnI₂ / tetrahydrofuran / 0.5 h / 0 °C

4.1: NaN[Si(CH₃)3]2 / tetrahydrofuran / 1 h / -78 °C

4.2: 94 percent / tetrahydrofuran / 4 h / -78 °C

With 1H-imidazole; sodium hexamethyldisilazane; diisobutylaluminium hydride; triphenylphosphine; zinc(II) iodide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol0165037

Reference yield:

: 182683-02-9
1-carbethoxy-5-tert-butyldimethylsilyloxycyclopent-1-ene

: 371115-19-4
4-(S)-benzyl-3-[2-(R)-(1-tert-butyldimethylsilyloxy-2-cyclopenten-2-yl)-methyl]-butyryl-2-oxazolidinone

Guidance literature:: Multi-step reaction with 3 steps

1.1: 77 percent / DIBAL-H / toluene; CH₂Cl₂ / 5 h / -70 °C

2.1: 69 percent / EtOOCN=NCOOEt; Ph₃P; ZnI₂ / tetrahydrofuran / 0.5 h / 0 °C

3.1: NaN[Si(CH₃)3]2 / tetrahydrofuran / 1 h / -78 °C

3.2: 94 percent / tetrahydrofuran / 4 h / -78 °C

With sodium hexamethyldisilazane; diisobutylaluminium hydride; triphenylphosphine; zinc(II) iodide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ol0165037