N-(p-Toluenesulfonyl)-L-phenylalanine

Base Information

• Chemical Name: N-(p-Toluenesulfonyl)-L-phenylalanine
• CAS No.: 13505-32-3
• Molecular Formula: C16H17NO4S
• Molecular Weight: 319.381
• Hs Code.: 29224999
• Nikkaji Number: J534.179E
• ChEMBL ID: CHEMBL3275993
• Mol file: 13505-32-3.mol

Synonyms:N-tosyl-(S)-phenylalanine

Chemical Property of N-(p-Toluenesulfonyl)-L-phenylalanine

Chemical Property:

• Vapor Pressure: 1.52E-11mmHg at 25°C
• Melting Point: 165 °C
• Refractive Index: -2.8 ° (C=4.5, Acetone)
• Boiling Point: 517.7°Cat760mmHg
• PKA: 3.31±0.10(Predicted)
• Flash Point: 266.9°C
• PSA: 91.85000
• Density: 1.303g/cm³
• LogP: 3.44090
• Storage Temp.: Store at RT.
• Solubility.: almost transparency in hot EtOH
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 319.08782920
• Heavy Atom Count: 22
• Complexity: 457

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Tosyl-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)NC(CC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)N[C@@H](CC2=CC=CC=C2)C(=O)O

Technology Process of N-(p-Toluenesulfonyl)-L-phenylalanine

There total 8 articles about N-(p-Toluenesulfonyl)-L-phenylalanine 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: 100.0%

N-(p-toluenesulfonyl) phenylalanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl) methyl ester (918886-05-2) → N-tosyl-(S)-phenylalanine (13505-32-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 0 ℃; for 9h;

DOI:10.1016/j.tet.2006.09.085

Reference yield: 99.93%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + p-toluenesulfonyl chloride (98-59-9) → N-tosyl-(S)-phenylalanine (13505-32-3)

Guidance literature:

With sodium carbonate; In water; for 5h;

DOI:10.1016/j.ejmech.2017.04.029

Reference yield: 90.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + toluene-4-sulfonic acid (104-15-4) → N-tosyl-(S)-phenylalanine (13505-32-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; for 2h; pH=> 8; Cooling with ice;

DOI:10.1016/j.ejmech.2020.112160

upstream raw materials:

1-Octyn-3-ol

N-(p-toluenesulfonyl)-L-phenylalanyl chloride

7-(N-tosyl-L-phenylalanyl)amino-4-nitrobenzo-2-oxa-1,3-diazole

L-phenylalanine

Downstream raw materials:

N-(p-toluenesulfonyl)-L-phenylalanyl chloride

(S)-4-methyl-N-(1-oxo-1,3-diphenylpropan-2-yl)benzenesulfonamide

L-phenylalanine

(S)-4-methyl-N-(1-oxo-3-phenylpropan-2-yl)-N-(prop-2-yn-1-yl)benzenesulfonamide

Refernces

• 1、 Zhang, Jinchao,Li, Luwei,Wang, Liwei,Zhang, Fangfang,Li, Xiaoliu. "Synthesis, characterization and cytotoxicity of mixed-ligand complexes of palladium(II) with aromatic diimine and 4-toluenesulfonyl-l-amino acid dianion". . p. 5337 - 5344. Retrieved 2010.
• 2、 Kuenstler, Th.,Schollmeyer, D.,Singer, H.,Steigerwald, H.. "SYNTHESIS OF OPTICALLY PURE ALKYNOLS". . p. 1645 - 1650. Retrieved 1993.
• 3、 Sivaraman, Aneesh,Kim, Dae Gyu,Bhattarai, Deepak,Kim, Minkyoung,Lee, Hwa Young,Lim, Semi,Kong, Jiwon,Goo, Ja-Il,Shim, Seunghwan,Lee, Seungbeom,Suh, Young-Ger,Choi, Yongseok,Kim, Sunghoon,Lee, Kyeong. "Synthesis and Structure-Activity Relationships of Arylsulfonamides as AIMP2-DX2 Inhibitors for the Development of a Novel Anticancer Therapy". . p. 5139 - 5158. Retrieved 2020/05/05.
• 4、 Lü, Zirui,Li, Xiaona,Niu, Yan,Sun, Qi,Wang, Chao,Xi, Dandan,Xu, Fengrong,Xu, Ping,Zhou, Tongliang. "Design and synthesis of tripeptidyl furylketones as selective inhibitors against the β5 subunit of human 20S proteasome". . . Retrieved 2020/03/10.