(S)-N-(p-tolylsulfinylimino)triphenylphosphorane

Base Information

• Chemical Name: (S)-N-(p-tolylsulfinylimino)triphenylphosphorane
• CAS No.: 216855-39-9
• Molecular Formula: C₂₅H₂₂NOPS
• Molecular Weight: 415.496
• Mol file: 216855-39-9.mol

Synonyms:(S)-N-(p-tolylsulfinylimino)triphenylphosphorane

Chemical Property of (S)-N-(p-tolylsulfinylimino)triphenylphosphorane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-N-(p-tolylsulfinylimino)triphenylphosphorane

There total 4 articles about (S)-N-(p-tolylsulfinylimino)triphenylphosphorane 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: 92.0%

triphenylphosphine (603-35-0) + (S)-p-toluenesulfinimide (188447-91-8) → (S)-N-(p-tolylsulfinylimino)triphenylphosphorane (216855-39-9)

Guidance literature:

With diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 0.666667h; to RT;

DOI:10.1016/S0040-4039(98)01698-0

Reference yield:

(1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate (1517-82-4) → (S)-N-(p-tolylsulfinylimino)triphenylphosphorane (216855-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiN(Me₃Si)2 / tetrahydrofuran / -70 °C

1.2: NH₄Cl / tetrahydrofuran; H₂O

2.1: 92 percent / DEAD / tetrahydrofuran / 0.67 h / 0 - 25 °C

With lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1002/1099-0690(200104)2001:8<1449::aid-ejoc1449>3.0.co;2-2

Reference yield:

(-)-menthyl p-toluenesulfinate (1517-82-4) → (S)-N-(p-tolylsulfinylimino)triphenylphosphorane (216855-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LiHMDS; 2.) NH₄Cl / 1.) THF, -70 deg C; 2.) H₂O

2: 92 percent / DEAD / tetrahydrofuran / 0.67 h / 0 °C / to RT

With ammonium chloride; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1016/S0040-4039(98)01698-0

upstream raw materials:

triphenylphosphine

(S)-p-toluenesulfinimide

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

(-)-menthyl p-toluenesulfinate

Downstream raw materials:

(S)-α-trifluoromethylleucine

DL-2-(Trifluoromethyl)leucine

(R)-(+)-3,3,3-trifluoro-2-amino-2-methylpropianoic acid

(S)-(-)-3,3,3-trifluoro-2-amino-2-methylpropianoic acid

Refernces

• 1、 Asensio, Amparo,Bravo, Pierfrancesco,Crucianelli, Marcello,Farina, Alessandra,Fustero, Santos,Soler, Juan García,Meille, Stefano V.,Panzeri, Walter,Viani, Fiorenza,Volonterio, Alessandro,Zanda, Matteo. "Synthesis of nonracemic α-trifluoromethyl α-amino acids from sulfinimines of trifluoropyruvate". . p. 1449 - 1458. Retrieved 2007/10/03.
• 2、 Bravo, Pierfrancesco,Crucianelli, Marcello,Zanda, Matteo. "First method for the preparation of strongly electrophilic chiral sulfinimines, and applications in asymmetric synthesis". . p. 345 - 346. Retrieved 2007/10/03.