Tosyl-L-phenylalanyl Chloride

Base Information

• Chemical Name: Tosyl-L-phenylalanyl Chloride
• CAS No.: 29739-88-6
• Molecular Formula: C₁₆H₁₆ClNO₃S
• Molecular Weight: 337.827
• Hs Code.: 2935009090
• European Community (EC) Number: 620-634-7
• DSSTox Substance ID: DTXSID10427087
• Nikkaji Number: J534.180I
• Mol file: 29739-88-6.mol

Synonyms:29739-88-6;N-(p-Toluenesulfonyl)-L-phenylalanyl Chloride;Tosyl-L-phenylalanyl Chloride;(2S)-2-[(4-methylphenyl)sulfonylamino]-3-phenylpropanoyl chloride;(S)-2-(4-Methylphenylsulfonamido)-3-phenylpropanoyl chloride;(2S)-2-(4-METHYLBENZENESULFONAMIDO)-3-PHENYLPROPANOYL CHLORIDE;N-(p-Tosyl)-L-phenylalaninyl chloride;SCHEMBL628639;Tosyl-L-phenylalaninoyl chloride;N-Tosyl-L-phenylalanine chloride;DTXSID10427087;KISOIDIHUAPEON-HNNXBMFYSA-N;STR05413;MFCD00191583;AKOS015897531;s12087;CS-0149404;N-p-Toluenesulphonyl-L-phenylalaninylchloride;T1444;J-017618;N-(P-TOLUENESULFONYL)-L-PHENYLALANYLCHLORIDE;(S)-2-(4-methylbenzenesulfonylamino)-3-phenylpropionyl chloride;Benzenepropanoyl chloride, alpha-[[(4-methylphenyl)sulfonyl]amino]-, (alphaS)-

Chemical Property of Tosyl-L-phenylalanyl Chloride

Chemical Property:

• Vapor Pressure: 7.91E-10mmHg at 25°C
• Melting Point: 132 °C (dec.)(lit.)
• Refractive Index: 10 ° (C=3, CHCl3)
• Boiling Point: 492.108 °C at 760 mmHg
• Flash Point: 251.418 °C
• PSA: 71.62000
• Density: 1.305 g/cm³
• LogP: 4.12170
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 337.0539422
• Heavy Atom Count: 22
• Complexity: 460

Purity/Quality:

99% ^*data from raw suppliers

N-(p-Toluenesulfonyl)-L-phenylalanyl Chloride [Optical Resolving Reagent for Alcohols] >97.0%(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 22-26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Tosyl-L-phenylalanyl Chloride

There total 6 articles about Tosyl-L-phenylalanyl Chloride 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-tosyl-(S)-phenylalanine (13505-32-3) → N-(p-toluenesulfonyl)-L-phenylalanyl chloride (90365-18-7,29739-88-6)

Guidance literature:

With thionyl chloride; In chloroform; at 20 ℃; for 3h; Reflux;

DOI:10.1021/jo300349f

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → N-(p-toluenesulfonyl)-L-phenylalanyl chloride (90365-18-7,29739-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 32 percent / aq. NaOH / diethyl ether / 16 h / 20 °C

2: PCl₅ / diethyl ether / 2 h / 20 °C

With sodium hydroxide; phosphorus pentachloride; In diethyl ether;

DOI:10.1039/b505324b

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → N-(p-toluenesulfonyl)-L-phenylalanyl chloride (90365-18-7,29739-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / aq. NaOH, Na₂CO₃ / diethyl ether / 30 h / Ambient temperature

2: 93 percent / PCl₅ / benzene / a.) 10 deg C, 2 h, b.) 20 deg C, 1 h

With sodium hydroxide; phosphorus pentachloride; sodium carbonate; In diethyl ether; benzene;

DOI:10.1080/00397919108019765

upstream raw materials:

N-tosyl-(S)-phenylalanine

L-phenylalanine

p-toluenesulfonyl chloride

Downstream raw materials:

N-(toluene-4-sulfonyl)-L-phenylalanyl=>L-glutaminyl=>L-asparagine

(R)-1-octyn-3-ol

N-tosyl-(S)-phenylalanine

(S)-1-octyn-3-yl N-(p-toluenesulfonyl)-(S)-phenylalaninate

Refernces

• 1、 Kanyiva, Kyalo Stephen,Tane, Marina,Shibata, Takanori. "Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling". . p. 12773 - 12783. Retrieved 2019/09/09.
• 2、 Ghosh, Debashis,Sadhukhan, Arghya,Maity, Nabin Ch.,Abdi, Sayed H. R.,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Bajaj, Hari C.. "Oxazoline derivatives tagged with tosylated amino acids as recyclable organocatalysts for enantioselective allylation of aldehydes". . p. 12257 - 12265. Retrieved 2014/03/21.