(R,E)-4-oxo-4-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-2-en-1-yl acetate

Base Information

Chemical Name:(R,E)-4-oxo-4-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-2-en-1-yl acetate
CAS No.:1333325-44-2
Molecular Formula:C₁₅H₁₅NO₅
Molecular Weight:289.288
Hs Code.:

Synonyms:(R,E)-4-oxo-4-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-2-en-1-yl acetate

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Chemical Property of (R,E)-4-oxo-4-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-2-en-1-yl acetate

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Technology Process of (R,E)-4-oxo-4-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-2-en-1-yl acetate

There total 1 articles about (R,E)-4-oxo-4-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-2-en-1-yl acetate 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: 43.0%

: 5371-49-3
acetoxyacetaldehyde

: 227602-33-7
diethyl (R)-2-oxo-2-(2-oxo-4-phenyloxazolidin-3-yl)ethylphosphonate

: 1333325-44-2
(R,E)-4-oxo-4-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-2-en-1-yl acetate

Guidance literature:: diethyl (R)-2-oxo-2-(2-oxo-4-phenyloxazolidin-3-yl)ethylphosphonate; With N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; at 20 ℃; for 0.333333h; Inert atmosphere;

acetoxyacetaldehyde; In tetrahydrofuran; at 20 ℃; for 18h;
DOI:10.1021/ol202265g

Reference yield: 77.0%

: 1333325-44-2
(R,E)-4-oxo-4-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-2-en-1-yl acetate

: 24850-33-7
allyltributylstanane

: 1333325-45-3
(S)-2-(2-oxo-2-((R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)ethyl)pent-4-en-1-yl acetate

Guidance literature:: (R,E)-4-oxo-4-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-2-en-1-yl acetate; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere;

allyltributylstanane; In dichloromethane; at -78 ℃; for 3h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/ol202265g

Reference yield:

: 1333325-44-2
(R,E)-4-oxo-4-(2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-2-en-1-yl acetate

: 1333325-46-4
(S)-2-(2-tert-butyldiphenylsilyloxyethyl)-4-oxo-4-((R)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl)but-1-yl acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: titanium tetrachloride / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water; tert-butyl alcohol / 2 h / 20 °C

3.1: dimethylsulfide borane complex / tetrahydrofuran / 0.17 h / 0 °C / Inert atmosphere

4.1: 1H-imidazole; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; dmap; sodium periodate; osmium(VIII) oxide; dimethylsulfide borane complex; titanium tetrachloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ol202265g