trans-(2R,3R)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]-1-[(S)-(p-toluenesulfinyl)]aziridine

Base Information

• Chemical Name: trans-(2R,3R)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]-1-[(S)-(p-toluenesulfinyl)]aziridine
• CAS No.: 909409-99-0
• Molecular Formula: C₂₈H₂₅NO₂S₂
• Molecular Weight: 471.644

Synonyms:trans-(2R,3R)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]-1-[(S)-(p-toluenesulfinyl)]aziridine

Chemical Property of trans-(2R,3R)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]-1-[(S)-(p-toluenesulfinyl)]aziridine

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Technology Process of trans-(2R,3R)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]-1-[(S)-(p-toluenesulfinyl)]aziridine

There total 2 articles about trans-(2R,3R)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]-1-[(S)-(p-toluenesulfinyl)]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: 50.0%

(S)-dimethyl[2-(p-toluenesulfinyl)phenyl]sulfonium perchlorate (1151538-22-5) + (S)-N-benzylidene-4-toluenesulfinamide (153277-49-7) → trans-(2R,3R)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]-1-[(S)-(p-toluenesulfinyl)]aziridine (909409-99-0) + trans-(2S,3S)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]-1-[(S)-(p-toluenesulfinyl)]aziridine

Guidance literature:

(S)-dimethyl[2-(p-toluenesulfinyl)phenyl]sulfonium perchlorate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

(S)-N-benzylidene-4-toluenesulfinamide; In tetrahydrofuran; at -78 ℃; for 0.166667h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jo900381b

Reference yield:

Dimethyl-{(1S,2R)-2-phenyl-2-((S)-toluene-4-sulfinylamino)-1-[2-((S)-toluene-4-sulfinyl)-phenyl]-ethyl}-sulfonium; perchlorate → trans-(2R,3R)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]-1-[(S)-(p-toluenesulfinyl)]aziridine (909409-99-0)

Guidance literature:

With potassium hydroxide; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2006.06.072

Reference yield: 75.0%

trans-(2R,3R)-2-phenyl-3-[(S)-2-(p-toluenesulfinyl)phenyl]-1-[(S)-(p-toluenesulfinyl)]aziridine (909409-99-0) → (+)-(2R,3R)-trans-2,3-diphenylaziridine (184674-48-4)

Guidance literature:

With tert.-butyl lithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

DOI:10.1016/j.tet.2006.06.072

upstream raw materials:

(S)-dimethyl[2-(p-toluenesulfinyl)phenyl]sulfonium perchlorate

(S)-N-benzylidene-4-toluenesulfinamide

Downstream raw materials:

(1S,2R)-2-amino-2-phenyl-1-[(R)-(2-p-toluenesulfinyl)phenyl]-ethanol

(+)-(2R,3R)-trans-2,3-diphenylaziridine

(1S,2R)-2-Amino-1,2-diphenylethanol

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