(2S,3S,4R)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

Base Information

Chemical Name:(2S,3S,4R)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate
CAS No.:1449124-89-3
Molecular Formula:C₂₈H₃₂N₂O₇S
Molecular Weight:540.637
Hs Code.:

Synonyms:(2S,3S,4R)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

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Chemical Property of (2S,3S,4R)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

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Technology Process of (2S,3S,4R)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

There total 5 articles about (2S,3S,4R)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate 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:

: 128217-49-2
(4S)-3-((E)-3'-(Ethoxycarbonyl)-2'-propenoyl)-4-(phenylmethyl)-2-oxazolidinone

: 2-(prop-1-en-2-yl)-1-tosylaziridine

: 1449124-89-3
(2S,3S,4R)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

: 1499138-42-9
(2S,3S,4S)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

Guidance literature:: (4S)-3-((E)-3'-(Ethoxycarbonyl)-2'-propenoyl)-4-(phenylmethyl)-2-oxazolidinone; With magnesium iodide; In tetrachloromethane; for 0.0833333h; Glovebox; Schlenk technique; Inert atmosphere;

2-(prop-1-en-2-yl)-1-tosylaziridine; In tetrachloromethane; at 20 ℃; for 16h; Overall yield = 63 %; Overall yield = 112 mg; enantioselective reaction; Glovebox; Schlenk technique; Inert atmosphere;
DOI:10.1021/ol4020333

Reference yield:

: 4124-41-8
p-toluenesulfonylanhydride

: 1449124-89-3
(2S,3S,4R)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

: 1499138-42-9
(2S,3S,4S)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: boron trifluoride diethyl etherate / dichloromethane; acetonitrile / 0.25 h / -78 °C / Inert atmosphere; Schlenk technique

1.2: 18 h / 20 °C / Inert atmosphere; Schlenk technique

2.1: magnesium iodide / tetrachloromethane / 0.08 h / Glovebox; Schlenk technique; Inert atmosphere

2.2: 16 h / 20 °C / Glovebox; Schlenk technique; Inert atmosphere

With boron trifluoride diethyl etherate; magnesium iodide; In tetrachloromethane; dichloromethane; acetonitrile;
DOI:10.1021/ol4020333

Reference yield:

: 2459-05-4
(E)-4-ethoxy-4-oxobut-2-enoic acid

: 1449124-89-3
(2S,3S,4R)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

: 1499138-42-9
(2S,3S,4S)-ethyl 3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: triethylamine; 2-chloro-1-methyl-pyridinium iodide / dichloromethane / 3 h / Reflux; Inert atmosphere; Schlenk technique

2.1: magnesium iodide / tetrachloromethane / 0.08 h / Glovebox; Schlenk technique; Inert atmosphere

2.2: 16 h / 20 °C / Glovebox; Schlenk technique; Inert atmosphere

With 2-chloro-1-methyl-pyridinium iodide; triethylamine; magnesium iodide; In tetrachloromethane; dichloromethane;
DOI:10.1021/ol4020333