(4S)-4-benzyl-3-{(2S)-2-[(S)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone

Base Information

Chemical Name:(4S)-4-benzyl-3-{(2S)-2-[(S)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone
CAS No.:853750-45-5
Molecular Formula:C₂₄H₂₇NO₆
Molecular Weight:425.481
Hs Code.:

Synonyms:(4S)-4-benzyl-3-{(2S)-2-[(S)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone

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Chemical Property of (4S)-4-benzyl-3-{(2S)-2-[(S)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone

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Technology Process of (4S)-4-benzyl-3-{(2S)-2-[(S)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone

There total 1 articles about (4S)-4-benzyl-3-{(2S)-2-[(S)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-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:

: 104266-88-8
(4S)-4-benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one

: 853750-45-5
(4S)-4-benzyl-3-{(2S)-2-[(S)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 0 °C

2: CH₂Cl₂ / 1.33 h / -65 - 0 °C

With triethylamine; In dichloromethane;
DOI:10.1039/b501151e

Reference yield: 97.0%

: 853750-45-5
(4S)-4-benzyl-3-{(2S)-2-[(S)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 1201327-93-6
(S)-4-benzyl-3-{(S)-2-[(S)-(3,4-dimethoxyphenyl)(triethylsilyloxy)-methyl]-4-pentenoyl}-2-oxazolidinone

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1271/bbb.90107

Reference yield:

: 853750-45-5
(4S)-4-benzyl-3-{(2S)-2-[(S)-(3,4-dimethoxyphenyl)(hydroxy)methyl]-4-pentenoyl}-2-oxazolidinone

: 853750-58-0
(2S,3R,4R,5R)-[5-benzo[1,3]dioxol-5-yl-2-(3,4-dimethoxyphenyl)-4-hydroxymethyl-tetrahydrofuran-3-yl]-methanol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

2.1: LiBH₄ / tetrahydrofuran; methanol / 16 h / 20 °C

3.1: aq. OsO₄; 4-methylmorpholine N-oxide / 2-methyl-propan-2-ol; acetone / 48 h / 20 °C

4.1: NaIO₄ / methanol / 16 h / 20 °C

5.1: PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 16 h / 20 °C

6.1: KHMDS / tetrahydrofuran; toluene / 0.25 h / -70 °C

6.2: tetrahydrofuran; toluene / 1 h / -70 °C

7.1: LiBH₄ / tetrahydrofuran / 24 h / 0 °C

8.1: pyridine / 0.5 h / 20 °C

9.1: PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 16 h / 20 °C

10.1: tetrabutylammonium fluoride; AcOH / tetrahydrofuran / 16 h / 20 °C

11.1: H₂ / Pd(OH)2/C / ethyl acetate / 1 h / 20 °C

12.1: aq. NaOH / ethanol / 20 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium borohydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; potassium hexamethylsilazane; acetic acid; 4-methylmorpholine N-oxide; pyridinium chlorochromate; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; acetone; toluene; tert-butyl alcohol;
DOI:10.1039/b501151e