(4S)-4-benzyl-3-[(2R)-2-methyl-3-(5-nitro-2,3,6-trimethoxyphenyl)-propionyl]-oxazolidin-2-one

Base Information

Chemical Name:(4S)-4-benzyl-3-[(2R)-2-methyl-3-(5-nitro-2,3,6-trimethoxyphenyl)-propionyl]-oxazolidin-2-one
CAS No.:326606-14-8
Molecular Formula:C₂₃H₂₆N₂O₈
Molecular Weight:458.468
Hs Code.:

Synonyms:(4S)-4-benzyl-3-[(2R)-2-methyl-3-(5-nitro-2,3,6-trimethoxyphenyl)-propionyl]-oxazolidin-2-one

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Chemical Property of (4S)-4-benzyl-3-[(2R)-2-methyl-3-(5-nitro-2,3,6-trimethoxyphenyl)-propionyl]-oxazolidin-2-one

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Technology Process of (4S)-4-benzyl-3-[(2R)-2-methyl-3-(5-nitro-2,3,6-trimethoxyphenyl)-propionyl]-oxazolidin-2-one

There total 5 articles about (4S)-4-benzyl-3-[(2R)-2-methyl-3-(5-nitro-2,3,6-trimethoxyphenyl)-propionyl]-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: 88.0%

: 131685-53-5,101711-78-8
(S)-4-benzyl-3-propionyl-2-oxazolidinone

: 326606-13-7
5-nitro-2,3,6-trimethoxybenzyl bromide

: (4S)-4-benzyl-3-[(2S)-2-methyl-3-(5-nitro-2,3,6-trimethoxyphenyl)-propionyl]-oxazolidin-2-one

: 326606-14-8
(4S)-4-benzyl-3-[(2R)-2-methyl-3-(5-nitro-2,3,6-trimethoxyphenyl)-propionyl]-oxazolidin-2-one

Guidance literature:: (S)-4-benzyl-3-propionyl-2-oxazolidinone; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.166667h;

5-nitro-2,3,6-trimethoxybenzyl bromide; In tetrahydrofuran; at -78 ℃; for 3.5h;
DOI:10.1021/ol0267432 DOI:10.1021/jo034870l

Reference yield:

: 135-77-3
1,2,4-trimethoxy-benzene

: 326606-14-8
(4S)-4-benzyl-3-[(2R)-2-methyl-3-(5-nitro-2,3,6-trimethoxyphenyl)-propionyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / diethyl ether; hexane / 2 h / Heating

1.2: 68 percent / diethyl ether; hexane / 2 h / Heating

2.1: 83 percent / HNO₃; AcOH / 0.5 h / 60 °C

3.1: 98 percent / NaBH₄ / tetrahydrofuran / 1 h / 20 °C

4.1: 93 percent / PBr₃; pyridine / diethyl ether / 0.5 h / 20 °C

5.1: 88 percent / NaHMDS / tetrahydrofuran / 3.5 h / -78 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; nitric acid; sodium hexamethyldisilazane; phosphorus tribromide; acetic acid; In tetrahydrofuran; diethyl ether; hexane; 5.1: Evan's asymmetric alkylation;
DOI:10.1021/ol0068997

Reference yield:

: 5556-86-5
2,3,6-trimethoxybenzaldehyde

: 326606-14-8
(4S)-4-benzyl-3-[(2R)-2-methyl-3-(5-nitro-2,3,6-trimethoxyphenyl)-propionyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 83 percent / HNO₃; AcOH / 0.5 h / 60 °C

2: 98 percent / NaBH₄ / tetrahydrofuran / 1 h / 20 °C

3: 93 percent / PBr₃; pyridine / diethyl ether / 0.5 h / 20 °C

4: 88 percent / NaHMDS / tetrahydrofuran / 3.5 h / -78 °C

With pyridine; sodium tetrahydroborate; nitric acid; sodium hexamethyldisilazane; phosphorus tribromide; acetic acid; In tetrahydrofuran; diethyl ether; 4: Evan's asymmetric alkylation;
DOI:10.1021/ol0068997