Tiamulin

Base Information

• Chemical Name: Tiamulin
• CAS No.: 55297-95-5
• Deprecated CAS: 56142-71-3
• Molecular Formula: C28H47NO4S
• Molecular Weight: 493.751
• Hs Code.: 2941906000
• European Community (EC) Number: 259-580-0
• UNII: E38WZ4U54R
• DSSTox Substance ID: DTXSID2046701
• Nikkaji Number: J12.323D
• Wikipedia: Tiamulin
• Wikidata: Q7800111
• NCI Thesaurus Code: C84207
• Metabolomics Workbench ID: 70032
• ChEMBL ID: CHEMBL1234521
• Mol file: 55297-95-5.mol

Synonyms:2-(diethylaminoethyl)thioacetoxymutilin;81723 HFU;Dynamutilin;tiamulin;tiamulin fumarate;tiamulin fumarate (1:1), (3aS-(3aalpha,4beta,5alpha,6alpha,8beta,9alpha,9abeta,10S*))-isomer;tiamulin hydrochloride;tiamutin

Chemical Property of Tiamulin

Chemical Property:

• Vapor Pressure: 5.06E-15mmHg at 25°C
• Melting Point: 147-148oC
• Refractive Index: 1.541
• Boiling Point: 563 °C at 760 mmHg
• PKA: 14.65±0.70(Predicted)
• Flash Point: 294.3 °C
• PSA: 92.14000
• Density: 1.1 g/cm³
• LogP: 4.96790
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 493.32258015
• Heavy Atom Count: 34
• Complexity: 770

Purity/Quality:

99% ^*data from raw suppliers

5-Hydroxy-4,6,9,10-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propanocyclopenta[8]annulen-8-yl hydroxyacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCN(CC)CCSCC(=O)OC1CC(C(C(C23CCC(C1(C2C(=O)CC3)C)C)C)O)(C)C=C
• Isomeric SMILES: CCN(CC)CCSCC(=O)O[C@@H]1C[C@@]([C@H]([C@@H]([C@@]23CC[C@H]([C@@]1([C@@H]2C(=O)CC3)C)C)C)O)(C)C=C
• Uses: Tiamulin is a semi–synthetic analogue of pleuromutilin in which the hydroxyacetyl side chain is replaced with a larger diethylaminoethylthioacetyl moiety, providing greater hydrophobicity and an ionisable group for salt formation and greater water solubility. Tiamulin is a potent and highly selective antibiotic active against a range of Gram positive bacteria, with no cross resistance to existing antibiotic classes due to its unique mode of action. Like pleuromutilin, it inhibits protein synthesis by binding to domain V of 23S rRNA. Tiamulin is a derivative of Pleuromutilin. Antibacterial.

Technology Process of Tiamulin

There total 3 articles about Tiamulin 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:

→ hydrogen fumarate salt + 14-Desoxy-14-[(2-diethylaminoethyl)mercaptoacetoxy]mutilin (55297-95-5)

Guidance literature:

Reference yield:

14-Deoxy-14-p-tosyloxyacetoxymutilin (31716-01-5,110043-77-1) + 2-(diethylamino)ethanethiol hydrochloride (1942-52-5) → tiamutin (55297-95-5)

Guidance literature:

With sodium ethanolate;

DOI:10.7164/antibiotics.29.915

Reference yield:

→ tiamutin (55297-95-5)

Guidance literature:

14-Desoxy-14-hydroxyacetoxymutilin, 1.) p-Toluolsulfochlorid, NaOH, H2O, 2.) Diethylaminoethanthiol-hydrochlorid, H2O, Benzyltributylammoniumbromid, 3.) NaOH/H2O;

upstream raw materials:

14-Deoxy-14-p-tosyloxyacetoxymutilin

2-(diethylamino)ethanethiol hydrochloride

Downstream raw materials:

(6R,7R)-7-((1R,3S)-1-Methoxy-3-methyl-4-oxo-5-phenylselanyl-3-vinyl-hexyl)-6,7-dimethyl-2,3,4,5,6,7-hexahydro-inden-1-one

Refernces

• 1、 Egger,Reinshagen. "New pleuromutilin derivatives with enhanced antimicrobial activity. I. Synthesis". . p. 915 - 922. Retrieved 2007/10/05.