(S_S,2R,3S)-(+)-ethyl 2-(N,N-dibenzylamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate

Base Information

• Chemical Name: (S_S,2R,3S)-(+)-ethyl 2-(N,N-dibenzylamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate
• CAS No.: 749253-89-2
• Molecular Formula: C₃₂H₃₄N₂O₃S
• Molecular Weight: 526.7

Synonyms:(S_S,2R,3S)-(+)-ethyl 2-(N,N-dibenzylamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate

Chemical Property of (S_S,2R,3S)-(+)-ethyl 2-(N,N-dibenzylamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate

Chemical Property:

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Technology Process of (S_S,2R,3S)-(+)-ethyl 2-(N,N-dibenzylamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate

There total 1 articles about (S_S,2R,3S)-(+)-ethyl 2-(N,N-dibenzylamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate 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: 68.0%

N,N-dibenzylglycine ethyl ester (77385-90-1) + (S,E)-N-benzylidene-4-methylbenzenesulfinamide (350479-90-2) → (SS,2R,3S)-(+)-ethyl 2-(N,N-dibenzylamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate (749253-89-2)

Guidance literature:

N,N-dibenzylglycine ethyl ester; With lithium diisopropyl amide; In tetrahydrofuran; cyclohexane; at -78 ℃; for 1h;

(S,E)-N-benzylidene-4-methylbenzenesulfinamide; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.5h;

DOI:10.1021/ol048981y

Reference yield:

(SS,2R,3S)-(+)-ethyl 2-(N,N-dibenzylamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate (749253-89-2) → (2R,3S)-3-Amino-2-dibenzylamino-3-phenyl-propionic acid ethyl ester

Guidance literature:

With trifluoroacetic acid; In ethanol; at 20 ℃; for 2h;

DOI:10.1021/ol048981y

Reference yield:

(SS,2R,3S)-(+)-ethyl 2-(N,N-dibenzylamino)-3-N-(p-toluenesulfinyl)amino-3-phenylpropanoate (749253-89-2) → (4R,5S)-(-)-4-(hydroxymethyl)-5-phenylimidazolidin-2-one

Guidance literature:

Multi-step reaction with 4 steps

1: TFA / ethanol / 2 h / 20 °C

2: 0.027 g / H₂ / Pd(OH)2 / ethanol / 12 h / 20 °C

3: 67 percent / CH₂Cl₂ / 4 h / Heating

4: 74 percent / NaBH₄ / tetrahydrofuran / 4 h

With sodium tetrahydroborate; hydrogen; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ol048981y

upstream raw materials:

N,N-dibenzylglycine ethyl ester

(S,E)-N-benzylidene-4-methylbenzenesulfinamide

Downstream raw materials:

(2R,3S)-(-)-ethyl 2,3-diamino-3-phenylpropanoate

(4R,5S)-(-)-ethyl 2-oxo-5-phenylimidazolidine-4-carboxylate

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