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

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Chemical Name:ethyl (4S,2E)-4-acetoxy-4-{(4R)-4-[(1S)-1-acetoxy-2-(benzyloxy)ethyl]-3-benzyl-2-oxooxazolidin-4-yl}but-2-enoate
CAS No.:1421940-26-2
Molecular Formula:C₂₉H₃₃NO₉
Molecular Weight:539.582
Hs Code.:

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

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

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

There total 5 articles about ethyl (4S,2E)-4-acetoxy-4-{(4R)-4-[(1S)-1-acetoxy-2-(benzyloxy)ethyl]-3-benzyl-2-oxooxazolidin-4-yl}but-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: 79.0%

: 1421940-24-0
ethyl (4S,2E)-4-{(4R)-3-benzyl-4-[(1S)-2-(benzyloxy)-1-hydroxyethyl]-2-oxooxazolidin-4-yl}-4-hydroxybut-2-enoate

: 108-24-7
acetic anhydride

: 1421940-26-2
ethyl (4S,2E)-4-acetoxy-4-{(4R)-4-[(1S)-1-acetoxy-2-(benzyloxy)ethyl]-3-benzyl-2-oxooxazolidin-4-yl}but-2-enoate

Guidance literature:: With pyridine; dmap; In toluene; at 20 ℃; for 18h; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.12.003

Reference yield:

: 1382153-80-1
(3aR,4'S,5S,6aR)-3'-benzyl-5-(hydroxymethyl)-2,2-dimethyldihydro-3aH-spiro[furo[2,3-d][1,3]dioxole-6,4'-oxazolidin]-2'-one

: 1421940-26-2
ethyl (4S,2E)-4-acetoxy-4-{(4R)-4-[(1S)-1-acetoxy-2-(benzyloxy)ethyl]-3-benzyl-2-oxooxazolidin-4-yl}but-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

1.2: 1.5 h / 0 - 20 °C / Inert atmosphere

2.1: trifluoroacetic acid / water / 3 h / 20 °C / Inert atmosphere

3.1: benzoic acid / water / 26.5 h / 20 °C / Inert atmosphere

4.1: pyridine; dmap / toluene / 18 h / 20 °C / Inert atmosphere

With pyridine; dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; benzoic acid; trifluoroacetic acid; In water; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1016/j.tetasy.2012.12.003

Reference yield:

: 1430738-72-9
C₂₁H₂₃NO₆

: 1421940-26-2
ethyl (4S,2E)-4-acetoxy-4-{(4R)-4-[(1S)-1-acetoxy-2-(benzyloxy)ethyl]-3-benzyl-2-oxooxazolidin-4-yl}but-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1: benzoic acid / water / 26.5 h / 20 °C / Inert atmosphere

2: pyridine; dmap / toluene / 18 h / 20 °C / Inert atmosphere

With pyridine; dmap; benzoic acid; In water; toluene;
DOI:10.1016/j.tetasy.2012.12.003