trans-(S_S,2S,3R)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine

Base Information

• Chemical Name: trans-(S_S,2S,3R)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine
• CAS No.: 158109-80-9
• Molecular Formula: C₁₇H₁₇NO₃S
• Molecular Weight: 315.393

Synonyms:trans-(S_S,2S,3R)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine

Chemical Property of trans-(S_S,2S,3R)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine

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Technology Process of trans-(S_S,2S,3R)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine

There total 2 articles about trans-(S_S,2S,3R)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-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: 89.0%

bromoacetic acid methyl ester (96-32-2) + (S,E)-N-benzylidene-4-methylbenzenesulfinamide (350479-90-2) → trans-(SS,2S,3R)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine (158109-80-9) + cis-(SS,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine (158009-37-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.333333h;

DOI:10.1021/jo990907j

Reference yield: 61.0%

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate (1517-82-4) + benzaldehyde (100-52-7) + bromoacetic acid methyl ester (96-32-2) → trans-(SS,2S,3R)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine (158109-80-9) + cis-(SS,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine (158009-37-1)

Guidance literature:

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate; With lithium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 1.5h;

benzaldehyde; In tetrahydrofuran; at -78 - 20 ℃; for 2h;

bromoacetic acid methyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -45 ℃; for 0.666667h;

DOI:10.1021/jo990907j

Reference yield: 95.0%

trans-(SS,2S,3R)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-phenylaziridine (158109-80-9) → trans-(2S,3R)-(-)-N-(p-toluenesulfonyl)-2-carbomethoxy-3-phenylaziridine

Guidance literature:

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

DOI:10.1021/jo990907j

upstream raw materials:

bromoacetic acid methyl ester

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

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate

benzaldehyde

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