THIOLACTOMYCIN

Base Information

• Chemical Name: THIOLACTOMYCIN
• CAS No.: 82079-32-1
• Molecular Formula: C11H14O2S
• Molecular Weight: 210.297
• Mol file: 82079-32-1.mol

Synonyms:[R-(E)]-4-Hydroxy-3,5-dimethyl-5-(2-methyl-1,3-butadienyl)-2(5H)-thiophenone;2(5H)-Thiophenone,3,5-dimethyl-4-hydroxy-5-(2-methyl-1,3-butadienyl)-,(R-(E));Antibiotic 2-200;TLM;(+)-Thiolactomycin;(R,E)-4-hydroxy-3,5-dimethyl-5-(2-methylbuta-1,3-dienyl)thiophen-2(5H)-one;(R-(E))-3,5-Dimethyl-4-hydroxy-5-(2-methyl-1,3-butadienyl)-2(5H)-thiophenone;(5R)-4-hydroxy-3,5-dimethyl-5-(2-methyl-buta-1,3-dienyl)-5-H-thiophen-2-one;(R)-(+)-Thiolactomycin;5R-Thiolactomycin;

Chemical Property of THIOLACTOMYCIN

Chemical Property:

• Vapor Pressure: 2.83E-05mmHg at 25°C
• Boiling Point: 319.2°Cat760mmHg
• Flash Point: 146.8°C
• PSA: 62.60000
• Density: 1.214g/cm³
• LogP: 2.98280
• Solubility.: DMSO: ~21 mg/mL, soluble

Purity/Quality:

99%, ^*data from raw suppliers

(R)-(+)-Thiolactomycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R)-(+)-Thiolactomycin is a natural product inhibitor of β-Ketoacyl-AcpM Synthase A (KasA). It inhibits the synthesis of mycolic acid which is a major cell wall component of Mycobacterium tuberculosis. Also an inhibitor of D-Aspartate oxidase (DDO).

Technology Process of THIOLACTOMYCIN

There total 20 articles about THIOLACTOMYCIN 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: 99.0%

(R)-4-Methoxy-3,5-dimethyl-5-((E)-2-methyl-buta-1,3-dienyl)-5H-thiophen-2-one (913941-71-6) → (+)-thiolactomycin (82079-32-1)

Guidance literature:

With lithium n-propylmercaptide; In N,N,N,N,N,N-hexamethylphosphoric triamide; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2006.07.152

Reference yield: 80.0%

(2R)-2,4-dimethyl-2-thiopropionyl-hexa-3,5-dienoic acid ethyl ester (476371-89-8) → (+)-thiolactomycin (82079-32-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -5 ℃; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b00236

Reference yield: 63.0%

(R,E)-benzyl 2,4-dimethyl-2-(propionylthio)hexa-3,5-dienoate (886733-89-7) → (+)-thiolactomycin (82079-32-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - 0 ℃;

DOI:10.1016/j.tetlet.2006.02.058

upstream raw materials:

(2R)-2,4-dimethyl-2-thiopropionyl-hexa-3,5-dienoic acid ethyl ester

(R,E)-benzyl 2,4-dimethyl-2-(propionylthio)hexa-3,5-dienoate

(R)-4-Methoxy-3,5-dimethyl-5-((E)-2-methyl-buta-1,3-dienyl)-5H-thiophen-2-one

(S)-3-Methoxy-2,4-dimethyl-5-oxo-2,5-dihydro-thiophene-2-carbaldehyde

Refernces

• 1、 Bommineni, Gopal R.,Kapilashrami, Kanishk,Cummings, Jason E.,Lu, Yang,Knudson, Susan E.,Gu, Chendi,Walker, Stephen G.,Slayden, Richard A.,Tonge, Peter J.. "Thiolactomycin-Based Inhibitors of Bacterial β-Ketoacyl-ACP Synthases with in Vivo Activity". . p. 5377 - 5390. Retrieved 2016.
• 2、 Ohata, Kohei,Terashima, Shiro. "Efficient synthesis and biological activity of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative". experimental part. p. 2244 - 2253. Retrieved 2009/08/07.