(2R)-2-azaniumyl-3-tritylsulfanylpropanoate

Base Information

• Chemical Name: (2R)-2-azaniumyl-3-tritylsulfanylpropanoate
• CAS No.: 2799-07-7
• Molecular Formula: C22H21NO2S
• Molecular Weight: 363.48
• Hs Code.: 29309090
• Pharos Ligand ID: M5RDQY9GG7B3
• Mol file: 2799-07-7.mol

Synonyms:(2R)-2-azaniumyl-3-tritylsulfanylpropanoate;(2R)-2-ammonio-3-[(triphenylmethyl)thio]propanoate;3ken

Chemical Property of (2R)-2-azaniumyl-3-tritylsulfanylpropanoate

Chemical Property:

• Appearance/Colour: almost white to light yellow granular powder
• Vapor Pressure: 7.71E-12mmHg at 25°C
• Melting Point: 182-183 °C (dec.)(lit.)
• Refractive Index: 111 ° (C=0.8, 0.04mol Ethanolic HCl)
• Boiling Point: 524.7 °C at 760 mmHg
• PKA: 2.22±0.10(Predicted)
• Flash Point: 271.2 °C
• PSA: 88.62000
• Density: 1.232 g/cm³
• LogP: 4.82390
• Storage Temp.: -20°C
• Solubility.: Soluble in DMSO (up to 20 mg/ml).
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 363.12930009
• Heavy Atom Count: 26
• Complexity: 386

Purity/Quality:

95% ^*data from raw suppliers

S-Trityl-L-cysteine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SCC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)SC[C@@H](C(=O)[O-])[NH3+]
• Description: S-Trityl-cysteine (2799-07-7) is a cell permeable inhibitor of mitotic kinesin Eg5 (IC50 for inhibition of basal ATPase activity = 1 μM; IC50 for inhibition of microtubule-activated ATPase activity = 140 nM). Mean growth concentration (GI50) of 1.31 μM for a panel of 60 different tumor cell lines.
• Uses: A protected cysteine for peptide synthesis. S-Trityl-L-cysteine (STLC) is a tight-binding inhibitor of Eg5 that prevents mitotic progression. It has proven antitumor activity as shown in the NCI 60 tumor cell line screen. (+)-S-Trityl-L-cysteine, a non-natural, sulfur-containing amino acid is commonly used as a reagent in solution phase peptide synthesis (SPPS). It is also used as a metal-binding agent to synthesize substituted ferrocenoyl peptide conjugates using HBTU peptide coupling reagent for the cation-sensing applications solution via peptide-metal interactions.

Technology Process of (2R)-2-azaniumyl-3-tritylsulfanylpropanoate

There total 16 articles about (2R)-2-azaniumyl-3-tritylsulfanylpropanoate 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: 98.0%

triphenylmethyl alcohol (76-84-6) + l-cysteine hydrochloride (52-89-1) → S-trityl-L-cysteine (2799-07-7)

Guidance literature:

triphenylmethyl alcohol; l-cysteine hydrochloride; With trifluoroacetic acid; for 2h;

With sodium acetate; sodium hydroxide; In diethyl ether; water; at 0 ℃; pH=5 - 6;

DOI:10.1016/j.ejmech.2012.02.018

Reference yield: 97.0%

l-cysteine hydrochloride (52-89-1) + trityl chloride (76-83-5) → S-trityl-L-cysteine (2799-07-7)

Guidance literature:

With sodium acetate; In water; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/acs.jmedchem.1c01583

Reference yield: 95.0%

triphenylmethyl alcohol (76-84-6) + L-Cysteine (52-90-4) → S-trityl-L-cysteine (2799-07-7)

Guidance literature:

With trifluoroacetic acid; at 20 ℃; for 0.5h;

DOI:10.1039/c9cc10043a

upstream raw materials:

triphenylmethyl alcohol

l-cysteine hydrochloride

trityl chloride

trifluoromethanesulfonic acid (R)-2,2,2-trifluoro-1-(4-fluorophenyl)ethyl ester

Downstream raw materials:

Form-Cys(Trit)OH

N-tert-butyloxycarbonyl-S-trityl-L-cysteine

(R)-2-[1-(4,4-Dimethyl-2,6-dioxo-cyclohexylidene)-ethylamino]-3-tritylsulfanyl-propionic acid

S-(triphenylmethyl)-L-cysteine tert-butyl ester

Refernces

• 1、 Hiskey,Adams. "". . p. 1340. Retrieved 1965.
• 2、 Quivelli, Andrea F.,D'Addato, Giovanna,Vitale, Paola,García-álvarez, Joaquín,Perna, Filippo M.,Capriati, Vito. "Expeditious and practical synthesis of tertiary alcohols from esters enabled by highly polarized organometallic compounds under aerobic conditions in Deep Eutectic Solvents or bulk water". . . Retrieved 2021/01/18.
• 3、 De La Fuente, M. Carmen,Jiménez, Carlos,Rodríguez, Jaime,Segade, Yuri,Valderrama, Katherine. "Convergent Total Synthesis of the Siderophore Piscibactin as Its Ga3+Complex". supporting information. p. 340 - 345. Retrieved 2021/01/13.