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

Base Information

• Chemical Name: trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine
• CAS No.: 181874-01-1
• Molecular Formula: C₁₈H₁₉NO₃S
• Molecular Weight: 329.42

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

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

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

There total 2 articles about trans-(S_S,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-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: 85.0%

Methyl 2-bromopropionate (5445-17-0) + (S,E)-N-benzylidene-4-methylbenzenesulfinamide (350479-90-2) → trans-(SS,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine (181874-01-1) + cis-(SS,2S,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine

Guidance literature:

Methyl 2-bromopropionate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.583333h;

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

DOI:10.1021/jo990907j

Reference yield: 84.0%

(S,E)-N-benzylidene-4-methylbenzenesulfinamide (350479-90-2) + Lithium; (E)-2-bromo-1-methoxy-propen-1-olate → trans-(SS,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine (181874-01-1)

Guidance literature:

at -78 ℃;

DOI:10.1016/S0040-4039(97)01095-2

Reference yield: 99.0%

trans-(SS,2R,3S)-(+)-N-(p-toluenesulfinyl)-2-methyl-2-carbomethoxy-3-phenylaziridine (181874-01-1) → trans-(2R,3S)-(+)-N-(p-toluenesulfonyl)-2-methyl-2-carbomethoxy-3-phenylaziridine (181874-04-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid;

DOI:10.1016/0040-4039(96)01168-9

upstream raw materials:

Methyl 2-bromopropionate

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

Downstream raw materials:

methyl (2R,3R)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoate

trans-(2R,3S)-(+)-N-(p-toluenesulfonyl)-2-methyl-2-carbomethoxy-3-phenylaziridine

(2R,3R)-(+)-2-methyl-3-(4-methylphenylsulfonamido)-3-phenylpropanoic acid

(1R,2R)-N-(3-hydroxy-2-methyl-1-phenyl-propyl)-4-methyl-benzenesulfonamide

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