Erteberel

Base Information

• Chemical Name: Erteberel
• CAS No.: 533884-09-2
• Molecular Formula: C18H18O3
• Molecular Weight: 282.33
• UNII: 2ZUL6758TZ
• DSSTox Substance ID: DTXSID70201547
• Wikipedia: Erteberel
• Wikidata: Q27097167
• NCI Thesaurus Code: C166610
• Pharos Ligand ID: QGKNH6XND9XP
• Metabolomics Workbench ID: 151086
• ChEMBL ID: CHEMBL278703
• Mol file: 533884-09-2.mol

Synonyms:erteberel;LY500307

Chemical Property of Erteberel

Chemical Property:

• Boiling Point: 485.2±45.0 °C(Predicted)
• PKA: 9.79±0.30(Predicted)
• PSA: 49.69000
• Density: 1.268
• LogP: 4.11520
• Solubility.: insoluble in H2O; ≥14.1 mg/mL in DMSO; ≥48.3 mg/mL in EtOH
• XLogP3: 4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 282.125594432
• Heavy Atom Count: 21
• Complexity: 364

Purity/Quality:

98% min ^*data from raw suppliers

Erteberel ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(C1)C3=C(C=CC(=C3)O)OC2C4=CC=C(C=C4)O
• Isomeric SMILES: C1C[C@H]2[C@@H](C1)C3=C(C=CC(=C3)O)O[C@H]2C4=CC=C(C=C4)O
• Recent ClinicalTrials: The Efficacy and Safety of a Selective Estrogen Receptor Beta Agonist (LY500307) for Negative Symptoms and Cognitive Impairment Associated With Schizophrenia
• Recent EU Clinical Trials: A Phase 2 Clinical Study to Evaluate Daily Oral Doses of LY500307 for 24 weeks in Men with Lower Urinary Tract Symptoms (LUTS) and Prostatic Enlargement Secondary to Benign Prostatic Hyperplasia (BPH).
• Uses: Erteberel is a highly selective estrogen receptor β (ERβ) agonist.

Technology Process of Erteberel

There total 29 articles about Erteberel 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: 90.0%

(4-(benzyloxy)phenyl)((1S,2R)-2-(2,5-bis(benzyloxy)phenyl)cyclopentyl)methanone (1357444-51-9) → Erteberel (533884-09-2)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; orthoformic acid triethyl ester; lithium bromide; In tetrahydrofuran; ethanol; for 6h; under 2585.81 Torr;

DOI:10.1021/ol203264a

Reference yield: 84.0%

C30H46O3Si2 → C18H18O3 (533884-09-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1002/ejoc.201800013

Reference yield:

2-(2,5-bis-methoxymethoxyphenyl)cyclopent-1-enecarboxylic acid methyl ester (533884-39-8) → Erteberel (533884-09-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 75 percent / H₂ / Pd/C / methanol / 12 h / 40 °C / 3102.89 Torr

2.1: 90 percent / isopropyl magnesium chloride / tetrahydrofuran / 0.5 h / -10 °C

3.1: s-BuLi / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

3.2: 97 percent / tetrahydrofuran; cyclohexane / 0.5 h / 0 °C

4.1: p-toluenesulfonic acid / methanol / 18 h / 50 °C

4.2: sodium cyanoborohydride; HCl / methanol / 1 h / 20 °C

With hydrogen; sec.-butyllithium; isopropylmagnesium chloride; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; cyclohexane;

DOI:10.1021/jm060491j

upstream raw materials:

2-(2,5-bis-methoxymethoxyphenyl)cyclopent-1-enecarboxylic acid methyl ester

methyl 2-(trifluoromethylsulfonyloxy)cyclopent-1-enecarboxylate

methyl 2-oxocyclopentane-1-carboxylate

8-(benzyloxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one

Refernces

• 1、 Calvin, Joel R.,Frederick, Michael O.,Laird, Dana L. T.,Remacle, Jacob R.,May, Scott A.. "Rhodium-catalyzed and zinc(II)-triflate-promoted asymmetric hydrogenation of tetrasubstituted α,β-unsaturated ketones". . p. 1038 - 1041. Retrieved 2012/04/10.
• 2、 Norman, Bryan H.,Dodge, Jeffrey A.,Richardson, Timothy I.,Borromeo, Peter S.,Lugar, Charles W.,Jones, Scott A.,Chen, Keyue,Wang, Yong,Durst, Gregory L.,Barr, Robert J.,Montrose-Rafizadeh, Chahrzad,Osborne, Harold E.,Amos, Robert M.,Guo, Sherry,Boodhoo, Amechand,Krishnan, Venkatesh. "Benzopyrans are selective estrogen receptor β agonists with novel activity in models of benign prostatic hyperplasia". . p. 6155 - 6157. Retrieved 2007/10/03.