(2S,3S,4R)-2-(ethoxycarbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-3-carboxylic acid

Base Information

Chemical Name:(2S,3S,4R)-2-(ethoxycarbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-3-carboxylic acid
CAS No.:1449124-95-1
Molecular Formula:C₁₈H₂₃NO₆S
Molecular Weight:381.45
Hs Code.:

Synonyms:(2S,3S,4R)-2-(ethoxycarbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-3-carboxylic acid

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Chemical Property of (2S,3S,4R)-2-(ethoxycarbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-3-carboxylic acid

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Technology Process of (2S,3S,4R)-2-(ethoxycarbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-3-carboxylic acid

There total 5 articles about (2S,3S,4R)-2-(ethoxycarbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-3-carboxylic acid 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: 77.0%

: 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

: 1449124-95-1
(2S,3S,4R)-2-(ethoxycarbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-3-carboxylic acid

Guidance literature:: With lithium hydroxide monohydrate; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 2h;
DOI:10.1021/ol4020333

Reference yield:

: 78-79-5,9003-31-0
isoprene

: 1449124-95-1
(2S,3S,4R)-2-(ethoxycarbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 3 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

3.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 0 °C

With lithium hydroxide monohydrate; boron trifluoride diethyl etherate; dihydrogen peroxide; magnesium iodide; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile;
DOI:10.1021/ol4020333

Reference yield:

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

: 1449124-95-1
(2S,3S,4R)-2-(ethoxycarbonyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-3-carboxylic acid

Guidance literature:: Multi-step reaction with 3 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

3.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 2 h / 0 °C

With lithium hydroxide monohydrate; 2-chloro-1-methyl-pyridinium iodide; dihydrogen peroxide; triethylamine; magnesium iodide; In tetrahydrofuran; tetrachloromethane; dichloromethane; water;
DOI:10.1021/ol4020333