Tilivalline

Base Information

• Chemical Name: Tilivalline
• CAS No.: 80279-24-9
• Molecular Formula: C₂₀H₁₉N₃O₂
• Molecular Weight: 333.39
• DSSTox Substance ID: DTXSID401001138
• Nikkaji Number: J648.107H
• Wikipedia: Tilivalline
• Wikidata: Q82994959
• Metabolomics Workbench ID: 98970
• Mol file: 80279-24-9.mol

Synonyms:epitilivalline;tilivalline

Chemical Property of Tilivalline

Chemical Property:

• Vapor Pressure: 1.72E-17mmHg at 25°C
• Melting Point: >215°C (dec.)
• Boiling Point: 649.9°C at 760 mmHg
• Flash Point: 346.8°C
• PSA: 68.36000
• Density: 1.43g/cm³
• LogP: 3.72080
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 333.147726857
• Heavy Atom Count: 25
• Complexity: 527

Purity/Quality:

Tilivalline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(NC3=C(C=CC=C3O)C(=O)N2C1)C4=CNC5=CC=CC=C54
• Isomeric SMILES: C1C[C@H]2[C@@H](NC3=C(C=CC=C3O)C(=O)N2C1)C4=CNC5=CC=CC=C54
• Uses: Tilivalline, is a metabolite from Klebsiella oxytoca. Tilivalline, is shown to be cytotoxin, and the key event causing Antibiotic-Associated Hemorrhagic Colitis.

Technology Process of Tilivalline

There total 28 articles about Tilivalline 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: 92.0%

(2S)-N-(3-benzyloxy-2-nitrobenzoyl)-2-pyrrolidinyl-3'-indolyl ketone (82354-31-2) → tilivalline (80279-24-9) + 11-epi-tilivalline (80279-25-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 4h; Heating;

DOI:10.1016/0040-4020(82)85058-8

Reference yield: 82.0%

(+)-(11S,11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-10-carbobenzyloxy-11-(3'-indolyl)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5-one (125299-55-0) → tilivalline (80279-24-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; under 1520 Torr;

DOI:10.1016/S0040-4039(00)99602-3

Reference yield: 80.0%

O-benzyltilivalline (110562-23-7) → tilivalline (80279-24-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4039(00)85411-8

upstream raw materials:

indole

(2-Amino-3-hydroxy-phenyl)-((S)-2-dimethoxymethyl-pyrrolidin-1-yl)-methanone

O-benzyltilivalline

(+)-(11S,11aS)-1,2,3,10,11,11a-hexahydro-9-(benzyloxy)-10-carbobenzyloxy-11-(3'-indolyl)-5H-pyrrolo<2,1-c><1,4>benzodiazepin-5-one

Downstream raw materials:

11-epi-tilivalline

Refernces

• 1、 Tse, Herman,Gu, Qiangshuai,Sze, Kong-Hung,Chu, Ivan K.,Kao, Richard Y.-T.,Lee, Kam-Chung,Lam, Ching-Wan,Yang, Dan,Shing-Chiu Tai, Sherlock,Ke, Yihong,Chan, Elaine,Chan, Wan-Mui,Dai, Jun,Leung, Sze-Pui,Leung, Suet-Yi,Yuen, Kwok-Yung. "A tricyclic pyrrolobenzodiazepine produced by Klebsiella oxytoca is associated with cytotoxicity in antibiotic-associated hemorrhagic colitis". . p. 19503 - 19520. Retrieved 2017/12/01.
• 2、 Mori, Shigehiro,Ohno, Tomoyasu,Harada, Hiroshi,Aoyama, Toyohiko,Shioiri, Takayuki. "New methods and reagents in organic synthesis. 92. A stereoselective synthesis of tilivalline and its analogs". . p. 5051 - 5070. Retrieved 2007/10/02.