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

Base Information

Chemical Name:(2S,4S)-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine
CAS No.:194994-16-6
Molecular Formula:C₃₉H₄₁N₃O₇S
Molecular Weight:695.836
Hs Code.:

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

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

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

There total 7 articles about (2S,4S)-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine 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: 73.0%

: 76-83-5
trityl chloride

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

: 194994-16-6
(2S,4S)-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

Guidance literature:: (2S,4S)-4-acetylthio-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)pyrrolidine; With sodium hydroxide; In methanol; at 20 ℃; for 0.5h;

trityl chloride; In N,N-dimethyl-formamide; at 50 ℃; for 10h;
DOI:10.7164/antibiotics.50.598

Reference yield:

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

: 194994-16-6
(2S,4S)-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

Guidance literature:: Multi-step reaction with 7 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

7.1: NaOH / methanol / 0.5 h / 20 °C

7.2: 73 percent / dimethylformamide / 10 h / 50 °C

With hydrogenchloride; dmap; sodium hydroxide; 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 / 7.1: Hydrolysis / 7.2: 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

: 194994-16-6
(2S,4S)-2-[1-hydroxy-3-(N-allyloxycarbonyl-N-methylamino)propyl]-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

Guidance literature:: Multi-step reaction with 5 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

5.1: NaOH / methanol / 0.5 h / 20 °C

5.2: 73 percent / dimethylformamide / 10 h / 50 °C

With hydrogenchloride; dmap; sodium hydroxide; 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 / 5.1: Hydrolysis / 5.2: Substitution;
DOI:10.7164/antibiotics.50.598