Larotaxel

Base Information

• Chemical Name: Larotaxel
• CAS No.: 156294-36-9
• Molecular Formula: C45H53NO14
• Molecular Weight: 831.914
• European Community (EC) Number: 682-335-8
• UNII: TWQ8K8A81Y
• Nikkaji Number: J912.846H
• Wikipedia: Larotaxel
• Wikidata: Q6489757
• NCI Thesaurus Code: C48427
• Metabolomics Workbench ID: 153866
• ChEMBL ID: CHEMBL4279455
• Mol file: 156294-36-9.mol

Synonyms:larotaxel;XRP 9881;XRP-9881;XRP9881

Chemical Property of Larotaxel

Chemical Property:

• Boiling Point: 889.3±65.0 °C(Predicted)
• PKA: 11.20±0.46(Predicted)
• PSA: 213.78000
• Density: 1.37
• LogP: 4.67390
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 15
• Exact Mass: 831.34660536
• Heavy Atom Count: 60
• Complexity: 1790

Purity/Quality:

97% ^*data from raw suppliers

Larotaxel ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(C(=O)C34CC3CC5C(C4C(C(C2(C)C)(CC1OC(=O)C(C(C6=CC=CC=C6)NC(=O)OC(C)(C)C)O)O)OC(=O)C7=CC=CC=C7)(CO5)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC1=C2[C@H](C(=O)[C@]34C[C@H]3C[C@@H]5[C@]([C@H]4[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C6=CC=CC=C6)NC(=O)OC(C)(C)C)O)O)OC(=O)C7=CC=CC=C7)(CO5)OC(=O)C)OC(=O)C
• Recent ClinicalTrials: Larotaxel Compared To Continuous Administration of 5-FU in Advanced Pancreatic Cancer Patients Previously Treated With A Gemcitabine-Containing Regimen
• Recent EU Clinical Trials: Randomized Study of LAROTAXEL + Cisplatin (LC) vs. Gemcitabine + Cisplatin (GC) in the First Line Treatment of Locally Advanced/Metastatic Urothelial Tract or Bladder Cancer
• Uses: Larotaxel (RPR 109881A) is a taxane analog with a broad spectrum of activity and different toxicity profile and with the possible advantages of surpassing some mechanisms of resistance and penetrating into the CNS.

Technology Process of Larotaxel

There total 13 articles about Larotaxel 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:

C51H67NO14Si → 7-deoxy-7β, 8β-methylene-10-O-acetyldocetaxel (156294-36-9)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 40 ℃; for 3h; pH=7;

DOI:10.1016/j.ejmech.2018.07.029

Reference yield:

(2α,3α,4α,5β,7α,10β,13α)-4,10-bis(acetyloxy)-13-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1-hydroxy-9-oxo-5,20-epoxy-7,19-cyclotax-11-en-2-yl benzoate (156294-35-8) → 7-deoxy-7β, 8β-methylene-10-O-acetyldocetaxel (156294-36-9)

Guidance literature:

With hydrogenchloride; In methanol; water; at 0 - 5 ℃; for 2.5h;

Reference yield:

10-acetyl-7-trifluoromethanesulfonate baccatin III (158811-19-9) → 7-deoxy-7β, 8β-methylene-10-O-acetyldocetaxel (156294-36-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium azide / acetonitrile / Inert atmosphere; Reflux

2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / -15 - 5 °C / Inert atmosphere

2.2: 1 h / -5 - 5 °C / Inert atmosphere

2.3: 1.5 h / Inert atmosphere

3.1: hydrogenchloride / water; methanol / 2.5 h / 0 - 5 °C

With hydrogenchloride; sodium azide; sodium hydride; In tetrahydrofuran; methanol; water; acetonitrile; mineral oil;

upstream raw materials:

10-deacetylbaccatin III

baccatin III

10-acetyl-7-trifluoromethanesulfonate baccatin III

7-deoxy-7β,8β-methanobaccatin III

Downstream raw materials:

larotaxel Cbz-glycinate

larotaxel Cbz-aminohexanoate

larotaxel aminohexanoate methanosulfonate

larotaxel glycinate methansulfonate