2-[(1s,2s)-2-Carboxycyclopropyl]-3-(9h-Xanthen-9-Yl)-D-Alanine

Base Information

• Chemical Name: 2-[(1s,2s)-2-Carboxycyclopropyl]-3-(9h-Xanthen-9-Yl)-D-Alanine
• CAS No.: 201943-63-7
• Molecular Formula: C₂₀H₁₉NO₅
• Molecular Weight: 353.375
• UNII: AQ73SP6QSF
• DSSTox Substance ID: DTXSID50942264
• Wikipedia: LY-341495
• Wikidata: Q6460424
• Pharos Ligand ID: 845C61APBLVB
• ChEMBL ID: CHEMBL432038
• Mol file: 201943-63-7.mol

Synonyms:2-amino-2-(2-carboxycycloprop-1-yl)-3-(xanth-9-yl)propanoic acid;LY 341495;LY-341495;LY341495

Chemical Property of 2-[(1s,2s)-2-Carboxycyclopropyl]-3-(9h-Xanthen-9-Yl)-D-Alanine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.669
• Boiling Point: 580.841 °C at 760 mmHg
• PKA: 2.02±0.10(Predicted)
• Flash Point: 305.082 °C
• PSA: 109.85000
• Density: 1.433 g/cm³
• LogP: 3.51740
• Storage Temp.: Store at RT
• Solubility.: Limited solubility, soluble in DMSO
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 353.12632271
• Heavy Atom Count: 26
• Complexity: 559

Purity/Quality:

98%min ^*data from raw suppliers

LY-341495 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C1C(CC2C3=CC=CC=C3OC4=CC=CC=C24)(C(=O)O)N)C(=O)O
• Isomeric SMILES: C1[C@@H]([C@H]1[C@@](CC2C3=CC=CC=C3OC4=CC=CC=C24)(C(=O)O)N)C(=O)O
• Uses: LY 341495 is a potent and selective antagonist of the group II metabotropic glutamate receptors (mGluR), mGluR2 and mGluR3 (IC50s = 21 and 14 nM, respectively, for human isoforms). It less effectively blocks mGluR8 and mGluR7 (IC50s = 173 and 990 nM, respectively) and weakly antagonizes mGluR1, mGluR5, and mGluR4 (IC50s = 6.8, 8.2, and 22 μM, respectively). In rat forebrain tissue, LY341495 may bind mGluR3 more avidly than mGluR2. LY341495 can be effectively used in isolated cells, tissues, and in vivo. In mice, it penetrates the blood-brain barrier and has been used to study the roles of mGlu2/3 receptors in the brain.[Cayman Chemical] LY-341495 is a potent and selective group II metabotropic glutamate receptor (mGluR) antagonist.

Technology Process of 2-[(1s,2s)-2-Carboxycyclopropyl]-3-(9h-Xanthen-9-Yl)-D-Alanine

There total 8 articles about 2-[(1s,2s)-2-Carboxycyclopropyl]-3-(9h-Xanthen-9-Yl)-D-Alanine 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: 52.0%

(1S,2S)-2-[(S)-1-(4-Methoxy-benzyl)-2,5-dioxo-4-(9H-xanthen-9-ylmethyl)-imidazolidin-4-yl]-cyclopropanecarboxylic acid 4-methoxy-benzyl ester → 2-[(1S,2S)-2-carboxycyclopropyl]-3-(9H-xanthen-9-yl)-D-alanine (201851-20-9,201943-63-7)

Guidance literature:

With sodium hydroxide; at 200 ℃; for 24h;

DOI:10.1021/jm970498o

Reference yield: 2.0%

(1R,2R)-2-[(S)-1-(4-Methoxy-benzyl)-2,5-dioxo-4-(9H-xanthen-9-ylmethyl)-imidazolidin-4-yl]-cyclopropanecarboxylic acid 4-methoxy-benzyl ester (201851-18-5) → LY 344545 (201943-63-7,201851-20-9)

Guidance literature:

With barium dihydroxide; at 200 ℃; for 24h;

DOI:10.1021/jm970498o

Reference yield:

(1R,2R)-cyclopropane-1,2-dicarboxylic acid bis-(1S,2R,5S)-(5-isopropyl-2-methyl-cyclohexyl) ester (96149-01-8) → LY 344545 (201943-63-7,201851-20-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 5 N aq. NaOH / propan-2-ol / 70 °C

2: SOCl₂ / Ambient temperature

3: 1.) Zn(Cu), 2.) Pd(Ph₃P)4 / 1.) benzene, N,N-dimethylacetamide, 60 deg C, 3 h, 2.) benzene, N,N-dimethylacetamide, RT, 1 h

4: 95 percent / 1 N aq. NaOH / ethanol / 23 h / 60 - 65 °C

5: ethanol; H₂O / 120 h / 55 °C

6: 43 percent / KHCO₃ / dimethylformamide / 125 °C

7: 2 percent / aq. Ba(OH)2 / 24 h / 200 °C

With barium dihydroxide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; zinc copper; potassium hydrogencarbonate; In ethanol; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jm970498o

upstream raw materials:

(1R,2R)-2-[(S)-1-(4-Methoxy-benzyl)-2,5-dioxo-4-(9H-xanthen-9-ylmethyl)-imidazolidin-4-yl]-cyclopropanecarboxylic acid 4-methoxy-benzyl ester

(1R,2R)-cyclopropane-1,2-dicarboxylic acid bis-(1S,2R,5S)-(5-isopropyl-2-methyl-cyclohexyl) ester

(1R,2R)-cyclopropane-1,2-dicarboxylic acid mono-(1S,2R,5S)-(5-isopropyl-2-methyl-cyclohexyl) ester

(1R,2R)-2-chlorocarbonyl-cyclopropanecarboxylic acid (1S,2R,5S)-5-isopropyl-2-methyl-cyclohexyl ester

Refernces