ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate

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Chemical Name:ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate
CAS No.:1382153-86-7
Molecular Formula:C₂₀H₂₅NO₈
Molecular Weight:407.42
Hs Code.:

Synonyms:ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate

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Chemical Property of ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate

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Technology Process of ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate

There total 6 articles about ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate 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: 68.0%

: 1382153-84-5
(5R,6S,8S,9R)-6-(acetoxymethyl)-1-benzyl-8,9-dihydroxy-3,7-dioxa-1-azaspiro [4.4]nonan-2-one

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1382153-86-7
ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate

Guidance literature:: With benzoic acid; In dichloromethane; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.04.012

Reference yield:

: 100-39-0
benzyl bromide

: 1382153-86-7
ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: pyridine; dmap / 0.5 h / 20 °C / Inert atmosphere

4.1: water; trifluoroacetic acid / 8.5 h / 20 °C / Inert atmosphere

5.1: benzoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

With pyridine; dmap; tetrabutyl ammonium fluoride; water; sodium hydride; benzoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil; 5.1: Wittig reaction;
DOI:10.1016/j.tetasy.2012.04.012

Reference yield:

: 1251959-23-5
(3aR,4'S,5S,6aR)-5-[(t-butyldimethylsilyloxy)methyl]-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4-oxazolidin]-2'-one

: 1382153-86-7
ethyl (4S,2E)-4-{(R)-4-[(S)-2-acetoxy-1-hydroxyethyl]-3-benzyl-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

3.1: pyridine; dmap / 0.5 h / 20 °C / Inert atmosphere

4.1: water; trifluoroacetic acid / 8.5 h / 20 °C / Inert atmosphere

5.1: benzoic acid / dichloromethane / 3 h / 20 °C / Inert atmosphere

With pyridine; dmap; tetrabutyl ammonium fluoride; water; sodium hydride; benzoic acid; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil; 5.1: Wittig reaction;
DOI:10.1016/j.tetasy.2012.04.012