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

Base Information

• Chemical Name: cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methylthiophenyl)aziridine
• CAS No.: 160751-26-8
• Molecular Formula: C₁₈H₁₉NO₃S₂
• Molecular Weight: 361.486

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

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

Chemical Property:

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

There total 2 articles about cis-(S_S,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methylthiophenyl)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: 71.0%

bromoacetic acid methyl ester (96-32-2) + (S)-(-)-N-<(p-methylthio)benzylidene>-p-toluenesulfinamide (160751-25-7) → cis-(SS,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methylthiophenyl)aziridine (160751-26-8)

Guidance literature:

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

(S)-(-)-N-<(p-methylthio)benzylidene>-p-toluenesulfinamide; In tetrahydrofuran; at -78 ℃; for 2.5h;

DOI:10.1021/jo990907j

Reference yield: 60.0%

(S)-(-)-N-<(p-methylthio)benzylidene>-p-toluenesulfinamide (160751-25-7) + lithium enolate of methyl bromoacetate → cis-(SS,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methylthiophenyl)aziridine (160751-26-8)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)78334-1

Reference yield: 87.0%

cis-(SS,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-carbomethoxy-3-(p-methylthiophenyl)aziridine (160751-26-8) → (2S,3S)-2-hydroxymethyl-3-(4-methylthiophenyl)-1H-aziridine (160751-27-9)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 1h; 0 deg C to r.t.;

DOI:10.1016/S0040-4039(00)78334-1

upstream raw materials:

(S)-(-)-N-<(p-methylthio)benzylidene>-p-toluenesulfinamide

bromoacetic acid methyl ester

Downstream raw materials:

(2S,3S)-2-hydroxymethyl-3-(4-methylthiophenyl)-1H-aziridine

thiamphenicol

(R*,R*)-(+)-thiomicamine

(1R,2R)-2-(2,2-dichloro-acetylamino)-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol

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