cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methoxyphenyl)aziridine

Base Information

• Chemical Name: cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methoxyphenyl)aziridine
• CAS No.: 158009-38-2
• Molecular Formula: C₁₈H₁₉NO₄S
• Molecular Weight: 345.419

Synonyms:cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methoxyphenyl)aziridine

Chemical Property of cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methoxyphenyl)aziridine

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Technology Process of cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methoxyphenyl)aziridine

There total 1 articles about cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methoxyphenyl)aziridine 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: 93.0%

bromoacetic acid methyl ester (96-32-2) + (S,E)-N-(4-methoxybenzylidene)-4-methylbenzenesulfinamide (158109-77-4) → (2S,3R)-3-(4-Methoxy-phenyl)-1-((S)-toluene-4-sulfinyl)-aziridine-2-carboxylic acid methyl ester + cis-(SS,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methoxyphenyl)aziridine (158009-38-2)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/jo990907j

Reference yield: 71.0%

methylmagnesium bromide (75-16-1) + cis-(SS,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methoxyphenyl)aziridine (158009-38-2) → (R)-methyl p-tolyl sulfoxide (1519-39-7) + methyl (2S,3S)-(+)-3-(p-methoxyphenyl)-1H-aziridine-2-carboxylate

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 ℃;

DOI:10.1021/jo990907j

Reference yield: 34.0%

cis-(SS,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methoxyphenyl)aziridine (158009-38-2) → methyl (2S,3R)-(+)-2-amino-3-hydroxy-3-(p-methoxyphenyl)propanoate + methyl (2S,3S)-(+)-2-amino-3-hydroxy-3-(p-methoxyphenyl)propanoate

Guidance literature:

With trifluoroacetic acid; In acetone;

DOI:10.1021/jo990907j

upstream raw materials:

bromoacetic acid methyl ester

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

Downstream raw materials:

(R)-methyl p-tolyl sulfoxide

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