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

Base Information

Chemical Name:(2S,3S,4R)-ethyl 3-(2-diazoacetyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate
CAS No.:1449124-96-2
Molecular Formula:C₁₉H₂₃N₃O₅S
Molecular Weight:405.475
Hs Code.:

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

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

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

There total 8 articles about (2S,3S,4R)-ethyl 3-(2-diazoacetyl)-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:

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

: 1449124-96-2
(2S,3S,4R)-ethyl 3-(2-diazoacetyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 5 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

4.1: oxalyl dichloride / 2 h / 70 °C / Inert atmosphere; Schlenk technique

5.1: tetrahydrofuran; hexane / 24 h / 0 - 4 °C / Inert atmosphere; Schlenk technique

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

Reference yield:

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

: 1449124-96-2
(2S,3S,4R)-ethyl 3-(2-diazoacetyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 5 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

4.1: oxalyl dichloride / 2 h / 70 °C / Inert atmosphere; Schlenk technique

5.1: tetrahydrofuran; hexane / 24 h / 0 - 4 °C / Inert atmosphere; Schlenk technique

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

Reference yield:

: 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

: 1449124-96-2
(2S,3S,4R)-ethyl 3-(2-diazoacetyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

2: oxalyl dichloride / 2 h / 70 °C / Inert atmosphere; Schlenk technique

3: tetrahydrofuran; hexane / 24 h / 0 - 4 °C / Inert atmosphere; Schlenk technique

With oxalyl dichloride; lithium hydroxide monohydrate; dihydrogen peroxide; In tetrahydrofuran; hexane; water;
DOI:10.1021/ol4020333