cis-(S_S,2S,3S)-(-)-N-p-toluenesulfinyl-2-carbomethoxy-3-methyl-3-phenylaziridine

Base Information

• Chemical Name: cis-(S_S,2S,3S)-(-)-N-p-toluenesulfinyl-2-carbomethoxy-3-methyl-3-phenylaziridine
• CAS No.: 250378-57-5
• Molecular Formula: C₁₈H₁₉NO₃S
• Molecular Weight: 329.42

Synonyms:cis-(S_S,2S,3S)-(-)-N-p-toluenesulfinyl-2-carbomethoxy-3-methyl-3-phenylaziridine

Chemical Property of cis-(S_S,2S,3S)-(-)-N-p-toluenesulfinyl-2-carbomethoxy-3-methyl-3-phenylaziridine

Chemical Property:

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Technology Process of cis-(S_S,2S,3S)-(-)-N-p-toluenesulfinyl-2-carbomethoxy-3-methyl-3-phenylaziridine

There total 1 articles about cis-(S_S,2S,3S)-(-)-N-p-toluenesulfinyl-2-carbomethoxy-3-methyl-3-phenylaziridine 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: 41.0%

[S-(E)]-(+)-N-α-methylbenzylidene-p-toluenesulfinamide (65440-68-8) + bromoacetic acid methyl ester (96-32-2) → [(1-phenyl-vinyl)-(toluene-4-sulfinyl)-amino]-acetic acid methyl ester + cis-(SS,2S,3S)-(-)-N-p-toluenesulfinyl-2-carbomethoxy-3-methyl-3-phenylaziridine (250378-57-5)

Guidance literature:

bromoacetic acid methyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

[S-(E)]-(+)-N-α-methylbenzylidene-p-toluenesulfinamide; In tetrahydrofuran; at -78 - 0 ℃; for 1.25h;

DOI:10.1021/jo990907j

Reference yield: 95.0%

cis-(SS,2S,3S)-(-)-N-p-toluenesulfinyl-2-carbomethoxy-3-methyl-3-phenylaziridine (250378-57-5) → cis-(2S,3S)-(-)-N-(p-toluenesulfonyl)-2-carbomethoxy-3-methyl-3-phenylaziridine (250378-51-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 25 ℃;

DOI:10.1021/jo990907j

Reference yield:

cis-(SS,2S,3S)-(-)-N-p-toluenesulfinyl-2-carbomethoxy-3-methyl-3-phenylaziridine (250378-57-5) → (2S,3R)-3-Phenyl-2-(toluene-4-sulfonylamino)-butyric acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / m-CPBA / CHCl₃ / 25 °C

2: formic acid / Pd / ethanol / 2 h / 20 °C

With formic acid; 3-chloro-benzenecarboperoxoic acid; palladium; In ethanol; chloroform; 1: Oxidation / 2: Ring cleavage;

DOI:10.1021/jo990907j

upstream raw materials:

[S-(E)]-(+)-N-α-methylbenzylidene-p-toluenesulfinamide

bromoacetic acid methyl ester

Downstream raw materials:

cis-(2S,3S)-(-)-N-(p-toluenesulfonyl)-2-carbomethoxy-3-methyl-3-phenylaziridine

(2S,3S)-methylphenylalanine

methyl (2S,3S)-(-)-2-N-(p-toluenesulfonyl)amino-3-phenylbutyrate

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