(2S,4S)-4-acetylthio-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)pyrrolidine

Base Information

Chemical Name:(2S,4S)-4-acetylthio-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)pyrrolidine
CAS No.:194994-15-5
Molecular Formula:C₂₂H₂₉N₃O₈S
Molecular Weight:495.554
Hs Code.:

Synonyms:(2S,4S)-4-acetylthio-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)pyrrolidine

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Chemical Property of (2S,4S)-4-acetylthio-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)pyrrolidine

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Technology Process of (2S,4S)-4-acetylthio-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)pyrrolidine

There total 5 articles about (2S,4S)-4-acetylthio-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)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: 74.0%

: 124-63-0
methanesulfonyl chloride

: 194994-14-4
(2S,4R)-4-hydroxy-2-{(R)-1-hydroxy-3-[N-allyloxycarbonyl-N-methylamino]propyl}-N-(p-nitrobenzyloxycarbonyl)pyrrolidine

: 10387-40-3
potassium thioacetate

: 194994-15-5
(2S,4S)-4-acetylthio-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: methanesulfonyl chloride; (2S,4R)-4-hydroxy-2-{(R)-1-hydroxy-3-[N-allyloxycarbonyl-N-methylamino]propyl}-N-(p-nitrobenzyloxycarbonyl)pyrrolidine; With triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

potassium thioacetate; In N,N-dimethyl-formamide; at 70 ℃; for 3h;
DOI:10.7164/antibiotics.50.598

Reference yield:

: 134441-71-7
(2S,4R)-1-boc-4-tert-butyldimethylsilylpyrrolidine-2-carbaldehyde

: 194994-15-5
(2S,4S)-4-acetylthio-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1.1: 62 percent / hexamethyldisilazane; n-BuLi / tetrahydrofuran; hexane / 0.5 h / -70 °C

2.1: NaBH₄ / tetrahydrofuran; methanol / 0.5 h / 65 °C

3.1: 74 percent / NEt₃; DMAP / CH₂Cl₂ / 1 h / 20 °C

4.1: methanol / 8 h

4.2: NEt₃ / CH₂Cl₂

5.1: HCl / methanol / 10 h / 20 °C

5.2: 73 percent / NEt₃ / methanol; CH₂Cl₂ / 0.5 h / -10 °C

6.1: NEt₃ / CH₂Cl₂ / 0.5 h / 0 °C

6.2: 74 percent / dimethylformamide / 3 h / 70 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; n-butyllithium; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.1: Addition / 2.1: Reduction / 3.1: Tosylation / 4.1: Substitution / 4.2: Substitution / 5.1: Hydrolysis / 5.2: Substitution / 6.1: Substitution / 6.2: Substitution;
DOI:10.7164/antibiotics.50.598

Reference yield:

: 149813-00-3
(3R,5S)-N-tert-butoxycarbonyl-3-tert-butyldimethylsilyloxy-5-((R)-1,3-dihydroxypropyl)pyrrolidine

: 194994-15-5
(2S,4S)-4-acetylthio-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 74 percent / NEt₃; DMAP / CH₂Cl₂ / 1 h / 20 °C

2.1: methanol / 8 h

2.2: NEt₃ / CH₂Cl₂

3.1: HCl / methanol / 10 h / 20 °C

3.2: 73 percent / NEt₃ / methanol; CH₂Cl₂ / 0.5 h / -10 °C

4.1: NEt₃ / CH₂Cl₂ / 0.5 h / 0 °C

4.2: 74 percent / dimethylformamide / 3 h / 70 °C

With hydrogenchloride; dmap; triethylamine; In methanol; dichloromethane; 1.1: Tosylation / 2.1: Substitution / 2.2: Substitution / 3.1: Hydrolysis / 3.2: Substitution / 4.1: Substitution / 4.2: Substitution;
DOI:10.7164/antibiotics.50.598