(S)-4-Benzyl-3-{(S)-2-[(S)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-but-3-enoyl}-oxazolidin-2-one

Base Information

Chemical Name:(S)-4-Benzyl-3-{(S)-2-[(S)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-but-3-enoyl}-oxazolidin-2-one
CAS No.:864369-29-9
Molecular Formula:C₂₃H₂₅NO₆
Molecular Weight:411.455
Hs Code.:

Synonyms:(S)-4-Benzyl-3-{(S)-2-[(S)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-but-3-enoyl}-oxazolidin-2-one

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Chemical Property of (S)-4-Benzyl-3-{(S)-2-[(S)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-but-3-enoyl}-oxazolidin-2-one

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Technology Process of (S)-4-Benzyl-3-{(S)-2-[(S)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-but-3-enoyl}-oxazolidin-2-one

There total 1 articles about (S)-4-Benzyl-3-{(S)-2-[(S)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-but-3-enoyl}-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: 87.0%

: 90719-30-5
(4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone

: 120-14-9
3,4-dimethoxy-benzaldehyde

: 864369-29-9
(S)-4-Benzyl-3-{(S)-2-[(S)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-but-3-enoyl}-oxazolidin-2-one

Guidance literature:: (4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane;

3,4-dimethoxy-benzaldehyde; In dichloromethane; at -78 - 0 ℃;
DOI:10.1021/ol051292h

Reference yield:

: 864369-29-9
(S)-4-Benzyl-3-{(S)-2-[(S)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-but-3-enoyl}-oxazolidin-2-one

: 26687-82-1,81446-30-2,84413-77-4,87678-74-8,87678-75-9,144901-91-7,7770-78-7
Arctigenin

Guidance literature:: Multi-step reaction with 6 steps

1: 1.45 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2: 85 percent / NaBH₄ / tetrahydrofuran; H₂O / 16 h / 25 °C

3: 88 percent / pyridine / CH₂Cl₂ / 1 h / 20 °C

4: 44 percent / (Me₃Si)3SiH; AIBN / benzene / 4 h / Heating

5: 86 percent / AcOH; (n-Bu)4NF / tetrahydrofuran / 336 h / 20 °C

6: 80 percent / H₂; HClO₄ / Pd/C / ethanol / 48 h / 3040 Torr

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; perchloric acid; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; tetrabutyl ammonium fluoride; hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; benzene;
DOI:10.1021/ol049878b

Reference yield:

: 864369-29-9
(S)-4-Benzyl-3-{(S)-2-[(S)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-but-3-enoyl}-oxazolidin-2-one

: (4S,2'S,3'S,4'S,5'S)-4-benzyl-3-[2'-(3,4-dimethoxyphenyl)-5'-phenethyl-4'-vinyltetrahydrofuran-3'-carbonyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / 20 °C

2: RuCl₂(Pcy₃)2=CHPh / CH₂Cl₂ / Heating

3: 41 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 5.75 h / -78 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; Grubbs catalyst first generation; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol051292h