(2S,4S)-2-{[2-(allyloxycarbonylamino)ethyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

Base Information

Chemical Name:(2S,4S)-2-{[2-(allyloxycarbonylamino)ethyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine
CAS No.:639457-05-9
Molecular Formula:C₃₄H₃₇N₃O₅S
Molecular Weight:599.751
Hs Code.:

Synonyms:(2S,4S)-2-{[2-(allyloxycarbonylamino)ethyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

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Chemical Property of (2S,4S)-2-{[2-(allyloxycarbonylamino)ethyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

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Technology Process of (2S,4S)-2-{[2-(allyloxycarbonylamino)ethyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

There total 6 articles about (2S,4S)-2-{[2-(allyloxycarbonylamino)ethyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine 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: 87.1%

: 2937-50-0
Allyl chloroformate

: 639457-04-8
(2S,4S)-2-[(2-aminoethyl)carbamoyl]-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

: 639457-05-9
(2S,4S)-2-{[2-(allyloxycarbonylamino)ethyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0223-5234(03)00143-0

Reference yield:

: 625388-36-5
(2S,4S)-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine-2-carboxylic acid methyl ester

: 639457-05-9
(2S,4S)-2-{[2-(allyloxycarbonylamino)ethyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 83.2 percent / NaOH / methanol / 5 h / 20 °C

2.1: triethylamine; ethyl chloroformate / CH₂Cl₂ / 0.5 h / 0 °C

2.2: 89.5 percent / CH₂Cl₂ / 1 h / 0 °C

3.1: 91.7 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

4.1: 85.4 percent / sodium azide / dimethylsulfoxide / 5 h / 70 °C

5.1: 86.4 percent / triphenylphosphine; H₂O / tetrahydrofuran / 4 h / 40 °C

6.1: 87.1 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

With sodium hydroxide; sodium azide; water; chloroformic acid ethyl ester; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/S0223-5234(03)00143-0

Reference yield:

: 639457-00-4
(2S,4S)-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine-2-carboxylic acid

: 639457-05-9
(2S,4S)-2-{[2-(allyloxycarbonylamino)ethyl]carbamoyl}-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine; ethyl chloroformate / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 89.5 percent / CH₂Cl₂ / 1 h / 0 °C

2.1: 91.7 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

3.1: 85.4 percent / sodium azide / dimethylsulfoxide / 5 h / 70 °C

4.1: 86.4 percent / triphenylphosphine; H₂O / tetrahydrofuran / 4 h / 40 °C

5.1: 87.1 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

With sodium azide; water; chloroformic acid ethyl ester; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/S0223-5234(03)00143-0