Pleuromutilin

Base Information

• Chemical Name: Pleuromutilin
• CAS No.: 125-65-5
• Molecular Formula: C₂₂H₃₄O₅
• Molecular Weight: 378.509
• Hs Code.: 2918199090
• European Community (EC) Number: 204-747-5
• Wikipedia: Pleuromutilin
• Wikidata: Q7204785
• NCI Thesaurus Code: C166672
• ChEMBL ID: CHEMBL2360152
• Mol file: 125-65-5.mol

Synonyms:Drosophilin B;octahydro-5,8-dihydroxy-4,6,9,10- tetramethyl-6-vinyl-3a,9-propano-3aH-cyclopenta- cycloocten-1(4H)-one 8-glycolate;pleuromutilin

Chemical Property of Pleuromutilin

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 2.38E-11mmHg at 25°C
• Melting Point: 170-171 °C
• Refractive Index: 1.537
• Boiling Point: 482.8 °C at 760 mmHg
• PKA: 12.91±0.10(Predicted)
• Flash Point: 158.7 °C
• PSA: 83.83000
• Density: 1.15 g/cm³
• LogP: 2.88520
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: >10mg/mL (warmed)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 378.24062418
• Heavy Atom Count: 27
• Complexity: 645

Purity/Quality:

95%, 99% ^*data from raw suppliers

Pleuromutilin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC23CCC(=O)C2C1(C(CC(C(C3C)O)(C)C=C)OC(=O)CO)C
• Recent EU Clinical Trials: A Randomised, Double-blind, Multicentre, Superiority Placebo-controlled, Phase III Study to Assess the Efficacy and Safety of Topical 1 SB-275833 Ointment versus Placebo Ointment Applied Twice Daily for 5 days in the Treatment of Adults and Paediatric Subjects with Impetigo
• Description: Pleuromutilin is an antibiotic derived from the fungus Clitopilus that inhibits bacterial protein synthesis by binding to bacterial ribosomes in the peptidyl transferase component of the 50S subunit and inhibiting peptide bond formation.
• Uses: Antibiotic substance produced by the basidiomycetes Pleurotus mutilus Pleuromutilin is a diterpene produced by several species of basidomycete, notably the genus Pleurotus, discovered in 1951. Pleuromutilin 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. Pleuromutilin inhibits protein synthesis by binding to domain V of 23S rRNA and this has led to the development of many semi-synthetic analogues as new generation antibiotics, such as tiamulin and retapamulin. Pleuromutilins such as tiamulin and valnemulin have been used for some time in veterinary medicine to treat swine infections. More recently a semisynthetic pleuromutilin, retapamulin, has been introduced as a topical treatment for Gram-positive infections in humans. Pleuromutilins inhibit the peptidyl transferase activity of the bacterial 50S ribosomal subunit by binding to the A site. Antibiotic substance produced by the basidiomycetes Pleurotus mutilus.

Technology Process of Pleuromutilin

There total 6 articles about Pleuromutilin 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: 88.0%

8-Glykoyl-1-methoxy-octahydro-4,6,9,10-tetramethyl-6-vinyl-3a,9-propano-3aH-cyclopentacycloocten-5(4H)on (76338-20-0) → Pleuromutilin (125-65-5,80924-94-3)

Guidance literature:

With hydrogenchloride; zinc(II) chloride; In 1,4-dioxane; at 25 ℃; for 4h;

DOI:10.1016/0040-4020(80)80078-0

Reference yield:

C30H45ClO5 → (+/-)-Pleuromutilin (125-65-5,80924-94-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 4.5 h / -40 - -15 °C

2: Li, anhydrous liquid NH₃ / tetrahydrofuran / 1 h / -33 °C

3: PCC / CH₂Cl₂ / 4 h / 25 °C

4: HCl / ethanol / 3 h / 25 °C

5: 1.) DMAP, 2.) 5percent aq.KOH / 1.) THF, 25 deg C, 12 h, 2.) methanol, 25 deg C, 8 h

With hydrogenchloride; dmap; potassium hydroxide; ammonia; lithium; pyridinium chlorochromate; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ja00203a043

Reference yield:

(1R,2R,3S,4S,6R,7R,8R,9S)-3,6-Bis-methoxymethoxy-2,4,7,14-tetramethyl-4-vinyl-tricyclo[5.4.3.01,8]tetradecan-9-ol (80878-40-6) → (+/-)-Pleuromutilin (125-65-5,80924-94-3)

Guidance literature:

Multi-step reaction with 3 steps

1: PCC / CH₂Cl₂ / 4 h / 25 °C

2: HCl / ethanol / 3 h / 25 °C

3: 1.) DMAP, 2.) 5percent aq.KOH / 1.) THF, 25 deg C, 12 h, 2.) methanol, 25 deg C, 8 h

With hydrogenchloride; dmap; potassium hydroxide; pyridinium chlorochromate; In ethanol; dichloromethane;

DOI:10.1021/ja00203a043

upstream raw materials:

8-Glykoyl-1-methoxy-octahydro-4,6,9,10-tetramethyl-6-vinyl-3a,9-propano-3aH-cyclopentacycloocten-5(4H)on

Acetic acid 2-methanesulfonyloxy-2-oxo-ethyl ester

(+/-)-Mutilin

(1R,2R,3S,4S,6R,7R,8R,9S)-3,6-Bis-methoxymethoxy-2,4,7,14-tetramethyl-4-vinyl-tricyclo[5.4.3.0^1,8]tetradecan-9-ol

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、 Boeckman, Robert K.,Springer, Dane M.,Alessi, Thomas R.. "Synthetic Studies Directed toward Naturally Occuring Cyclooctanoids. 2. A Stereocontrolled Assembly of (+/-)-Pleuromutilin via a Remarkable Sterically Demanding Oxy-Cope Rearrangement". . p. 8284 - 8286. Retrieved 2007/10/02.