(R)-2-Acetylthio-3-phenylpropionic Acid

Base Information

• Chemical Name: (R)-2-Acetylthio-3-phenylpropionic Acid
• CAS No.: 57359-76-9
• Molecular Formula: C11H12O3S
• Molecular Weight: 224.28
• DSSTox Substance ID: DTXSID90431066
• Nikkaji Number: J1.175.559C
• Wikidata: Q82244864
• ChEMBL ID: CHEMBL87421
• Mol file: 57359-76-9.mol

Synonyms:(R)-2-Acetylthio-3-phenylpropionic Acid;57359-76-9;(2R)-2-acetylsulfanyl-3-phenylpropanoic acid;CHEMBL87421;2-(R)-Acetylthio-benzenepropanoic acid;SCHEMBL4842827;DTXSID90431066;BDBM50081017;(2R)-2-(Acetylthio)-3-phenylpropionic acid;(R)-2-Acetylsulfanyl-3-phenyl-propionic acid

Chemical Property of (R)-2-Acetylthio-3-phenylpropionic Acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.581
• Boiling Point: 358.93°C at 760 mmHg
• Flash Point: 170.875°C
• PSA: 79.67000
• Density: 1.261g/cm³
• LogP: 1.96200
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 224.05071541
• Heavy Atom Count: 15
• Complexity: 234

Purity/Quality:

98%Min ^*data from raw suppliers

(R)-2-Acetylthio-3-phenylpropionicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)SC(CC1=CC=CC=C1)C(=O)O
• Isomeric SMILES: CC(=O)S[C@H](CC1=CC=CC=C1)C(=O)O
• Uses: A IMP-1 metallo-?lactamase inhibitor. A IMP-1 metallo-β-lactamase inhibitor.

Technology Process of (R)-2-Acetylthio-3-phenylpropionic Acid

There total 15 articles about (R)-2-Acetylthio-3-phenylpropionic Acid 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%

(S)-2-bromo-3-phenylpropionic acid (35016-63-8) + sodium thioacetate (34832-35-4) → (2R)-2-(acetylthio)-3-phenylpropanoic acid (57359-76-9)

Guidance literature:

In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/jm950590p

Reference yield: 90.0%

(S)-2-bromo-3-phenylpropionic acid (35016-63-8) + potassium thioacetate (10387-40-3) → (2R)-2-(acetylthio)-3-phenylpropanoic acid (57359-76-9)

Guidance literature:

In methanol; for 12h; Ambient temperature;

DOI:10.1016/S0040-4039(00)60317-9

Reference yield: 45.0%

L-3-phenyllactic acid (20312-36-1) + tiolacetic acid (507-09-5) → (2R)-2-(acetylthio)-3-phenylpropanoic acid (57359-76-9) + (S)-2-acetylthio-3-phenylpropanoic acid (76932-17-7)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; Title compound not separated from byproducts; 1.) 0 deg C, 15 min; 2.) 0 deg C; 15 min without cooling;

DOI:10.1002/recl.19871061006

upstream raw materials:

(S)-2-bromo-3-phenylpropionic acid

potassium thioacetate

L-3-phenyllactic acid

tiolacetic acid

Downstream raw materials:

(R)-2-((R)-1-Carboxy-2-phenyl-ethylsulfanyl)-3-phenyl-propionic acid

(S)-2-((S)-1-Carboxy-2-phenyl-ethylsulfanyl)-3-phenyl-propionic acid

[14C]-(S)-3-phenyl-2-mercaptopropionic acid

(R)-2-((R)-1-Carbamoyl-2-phenyl-ethylsulfanyl)-3-phenyl-propionamide

Refernces

• 1、 Cui, Yong-Mei,Li, Jing-Ya,Chen, Ling-Ling,Li, Jia,Ye, Qi-Zhuang,Nan, Fa-Jun. "Design and synthesis of chromogenic thiopeptolide substrates as MetAPs active site probes". . p. 2853 - 2861. Retrieved 2007/10/03.
• 2、 Greenlee, Mark L.,Laub, Joanne B.,Balkovec, James M.,Hammond, Milton L.,Hammond, Gail G.,Pompliano, David L.,Epstein-Toney, Jeffrey H.. "Synthesis and SAR of thioester and thiol inhibitors of IMP-1 metallo-β-lactamase". . p. 2549 - 2554. Retrieved 2007/10/03.