(2R,4S)-2-{2-(Cyclopropanecarbonyl-amino)-2-[(Z)-hydroxyimino]-ethyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

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Chemical Name:(2R,4S)-2-{2-(Cyclopropanecarbonyl-amino)-2-[(Z)-hydroxyimino]-ethyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester
CAS No.:625388-45-6
Molecular Formula:C₃₃H₃₅N₃O₄S
Molecular Weight:569.725
Hs Code.:

Synonyms:(2R,4S)-2-{2-(Cyclopropanecarbonyl-amino)-2-[(Z)-hydroxyimino]-ethyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

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Chemical Property of (2R,4S)-2-{2-(Cyclopropanecarbonyl-amino)-2-[(Z)-hydroxyimino]-ethyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

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Technology Process of (2R,4S)-2-{2-(Cyclopropanecarbonyl-amino)-2-[(Z)-hydroxyimino]-ethyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

There total 8 articles about (2R,4S)-2-{2-(Cyclopropanecarbonyl-amino)-2-[(Z)-hydroxyimino]-ethyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester 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: 87.8%

: 4023-34-1
cyclopropanecarboxylic acid chloride

: 625388-37-6
(2S,4S)-2-(2-amino-2-(hydroxyimino)ethyl)-4-tritylthio-1-(allyloxycarbonyl)pyrrolidine

: 625388-45-6
(2R,4S)-2-{2-(Cyclopropanecarbonyl-amino)-2-[(Z)-hydroxyimino]-ethyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0223-5234(03)00116-8

Reference yield:

: 3695-77-0
triphenylmethanethiol

: 625388-45-6
(2R,4S)-2-{2-(Cyclopropanecarbonyl-amino)-2-[(Z)-hydroxyimino]-ethyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 82.5 percent / sodium hydride / dimethylformamide / 0 - 20 °C

2: 78.5 percent / LiBH₄ / tetrahydrofuran / 25 h / 20 °C

3: 94.8 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

4: 89.1 percent / dimethylsulfoxide / 5 h / 75 °C

5: 77.1 percent / hydroxylamine hydrochloride; Na₂CO₃ / ethanol; H₂O / 20 h / 60 °C

6: 87.8 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

With lithium borohydride; hydroxylamine hydrochloride; sodium hydride; sodium carbonate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0223-5234(03)00116-8

Reference yield:

: 126408-14-8
methyl (2S,4R)-N-(allyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate

: 625388-45-6
(2R,4S)-2-{2-(Cyclopropanecarbonyl-amino)-2-[(Z)-hydroxyimino]-ethyl}-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 93.2 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

2: 82.5 percent / sodium hydride / dimethylformamide / 0 - 20 °C

3: 78.5 percent / LiBH₄ / tetrahydrofuran / 25 h / 20 °C

4: 94.8 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

5: 89.1 percent / dimethylsulfoxide / 5 h / 75 °C

6: 77.1 percent / hydroxylamine hydrochloride; Na₂CO₃ / ethanol; H₂O / 20 h / 60 °C

7: 87.8 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

With lithium borohydride; hydroxylamine hydrochloride; sodium hydride; sodium carbonate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/S0223-5234(03)00116-8