(4S)-benzyl-3-(((2S,3S)-1-ethoxy-2-hydroxy-1-oxo-4-penten-3-yl)carbonyl)-1,3-oxazolidin-2-one

Base Information

Chemical Name:(4S)-benzyl-3-(((2S,3S)-1-ethoxy-2-hydroxy-1-oxo-4-penten-3-yl)carbonyl)-1,3-oxazolidin-2-one
CAS No.:907189-02-0
Molecular Formula:C₁₈H₂₁NO₆
Molecular Weight:347.368
Hs Code.:

Synonyms:(4S)-benzyl-3-(((2S,3S)-1-ethoxy-2-hydroxy-1-oxo-4-penten-3-yl)carbonyl)-1,3-oxazolidin-2-one

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Chemical Property of (4S)-benzyl-3-(((2S,3S)-1-ethoxy-2-hydroxy-1-oxo-4-penten-3-yl)carbonyl)-1,3-oxazolidin-2-one

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Technology Process of (4S)-benzyl-3-(((2S,3S)-1-ethoxy-2-hydroxy-1-oxo-4-penten-3-yl)carbonyl)-1,3-oxazolidin-2-one

There total 1 articles about (4S)-benzyl-3-(((2S,3S)-1-ethoxy-2-hydroxy-1-oxo-4-penten-3-yl)carbonyl)-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: 72.0%

: 924-44-7
glyoxylic acid ethyl ester

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

: 907189-02-0
(4S)-benzyl-3-(((2S,3S)-1-ethoxy-2-hydroxy-1-oxo-4-penten-3-yl)carbonyl)-1,3-oxazolidin-2-one

Guidance literature:: (4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃; for 1.25h;

glyoxylic acid ethyl ester; In dichloromethane; at -78 - 0 ℃; for 2h;
DOI:10.1021/jo060931e

Reference yield:

: 907189-02-0
(4S)-benzyl-3-(((2S,3S)-1-ethoxy-2-hydroxy-1-oxo-4-penten-3-yl)carbonyl)-1,3-oxazolidin-2-one

: tert-butyl (S)-2-((S)-2-((2S,4S)-2-tert-butyl-4-tert-butyloxycarbonylmethyl-5-oxo-1,3-dioxolan-4-yl)-11-oxo-octadec-3E-enoylamino)-3-phenylpropanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: LiOH; H₂O₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

2.1: LiOH / methanol; H₂O / 20 °C

3.1: i-Pr₂NEt / tetrahydrofuran / 2 h / 25 °C

4.1: 79 percent / Me₃SiOTf / CH₂Cl₂ / 16 h / -35 °C

5.1: lithium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0.83 h / -70 °C

5.2: 61 percent / tetrahydrofuran; dimethylformamide / 0.25 h / -70 °C

6.1: 57 percent / Grela catalyst / CH₂Cl₂ / 4 h / 65 °C / microwave irradiation

7.1: 34 mg / i-Pr₂NEt; HBTU; 1-hydroxybenzotriazole / dimethylformamide / 2 h / 0 °C

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; Grela catalyst; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo060931e

Reference yield:

: 907189-02-0
(4S)-benzyl-3-(((2S,3S)-1-ethoxy-2-hydroxy-1-oxo-4-penten-3-yl)carbonyl)-1,3-oxazolidin-2-one

: tert-butyl (3S,4S)-4-((1S)-1-tert-butyloxycarbonyl)-2-((tert-butyloxycarbonylphenyl)ethylaminocarbonyl)-3-hydroxy-3-(methoxycarbonyl)-13-oxo-5E-eicosenoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: LiOH; H₂O₂ / tetrahydrofuran; H₂O / 2 h / 0 °C

2.1: LiOH / methanol; H₂O / 20 °C

3.1: i-Pr₂NEt / tetrahydrofuran / 2 h / 25 °C

4.1: 79 percent / Me₃SiOTf / CH₂Cl₂ / 16 h / -35 °C

5.1: lithium hexamethyldisilazide / tetrahydrofuran; dimethylformamide / 0.83 h / -70 °C

5.2: 61 percent / tetrahydrofuran; dimethylformamide / 0.25 h / -70 °C

6.1: 57 percent / Grela catalyst / CH₂Cl₂ / 4 h / 65 °C / microwave irradiation

7.1: K₂CO₃ / 18 h / 25 °C

8.1: i-Pr₂NEt; HBTU; 1-hydroxybenzotriazole / dimethylformamide / 2 h / 0 - 20 °C

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; potassium carbonate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; Grela catalyst; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo060931e