Mutilin

Base Information

• Chemical Name: Mutilin
• CAS No.: 6040-37-5
• Molecular Formula: C20H32O3
• Molecular Weight: 320.47
• Mol file: 6040-37-5.mol

Synonyms:

Chemical Property of Mutilin

Chemical Property:

• Melting Point: 68-70 °C
• Boiling Point: 427.7±45.0 °C(Predicted)
• PKA: 14.61±0.70(Predicted)
• PSA: 57.53000
• Density: 1.09±0.1 g/cm3(Predicted)
• LogP: 3.34200
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Sparingly, Sonicated), Ethyl Acetate (Slightly)

Purity/Quality:

99%, ^*data from raw suppliers

Mutilin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Mutilin is minor metabolite of the pleuromutilin family, originally isolated from Pleurotus mutilus. Mutilin is formed by hydrolysis of the hydroxyacetyl ester of pleuromutilin, and is a degradation product and in vivo metabolite of pleuromutilin. Interest in mutilin has focused on its potential as a substrate for generating unique metabolites via biosynthesis to provide a broader range of targets for semi-synthetic modification. Mutilin, is used to perform biological studies with focus on antimicrobial activity. This complex is also a reagent in the production of pleuromutilin derivatives.

Technology Process of Mutilin

There total 22 articles about Mutilin 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: 98.0%

pleuromutilin → (3aR,4R,5R,7S,8S,9R,9aS,12R)-5,8-dihydroxy-4,7,9,12-tetramethyl-7-vinyloctahydro-4,9a-propanocyclopenta[8]annulen-3(3aH)-one (6040-37-5)

Guidance literature:

With water; sodium hydroxide; In ethanol; at 50 ℃; for 3h;

Reference yield: 74.0%

11,14-O,O-bis(methoxymethyl)mutilin → (3aR,4R,5R,7S,8S,9R,9aS,12R)-5,8-dihydroxy-4,7,9,12-tetramethyl-7-vinyloctahydro-4,9a-propanocyclopenta[8]annulen-3(3aH)-one (6040-37-5)

Guidance literature:

With acetyl chloride; In ethanol; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/chem.201300968

Reference yield:

(1S,2R,3S,4S,6R,7R,8R)-3,6-Bis-methoxymethoxy-2,4,7,14-tetramethyl-4-vinyl-tricyclo[5.4.3.01,8]tetradecan-9-one (80878-41-7) → (+/-)-Mutilin (6040-37-5,80924-95-4,87680-55-5,90582-78-8)

Guidance literature:

With hydrogenchloride; In ethanol; at 25 ℃; for 3h; Yield given;

DOI:10.1021/ja00203a043

upstream raw materials:

8-glycoloyloxy-5-hydroxy-4,6,9,10-tetramethyl-6-vinyl-octahydro-3a,9-propano-cyclopentacycloocten-1-one

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

(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

(1S,2S,3R,4R,6S,7S,8S,9R)-9-Benzyloxy-3,6-bis-methoxymethoxy-2,4,7,14-tetramethyl-4-vinyl-tricyclo[5.4.3.0^1,8]tetradecane

Downstream raw materials:

(+/-)-Pleuromutilin

Refernces

• 1、 Hicklin, Robert W.,Lopez Silva, Tania L.,Hergenrother, Paul J.. "Synthesis of bridged oxafenestranes from pleuromutilin". . p. 9880 - 9883,4. Retrieved 2014.
• 2、 Llabani, Evijola,Hicklin, Robert W.,Lee, Hyang Yeon,Motika, Stephen E.,Crawford, Lisa A.,Weerapana, Eranthie,Hergenrother, Paul J.. "Diverse compounds from pleuromutilin lead to a thioredoxin inhibitor and inducer of ferroptosis". . p. 521 - 532. Retrieved 2019.
• 3、 -. "Diterpene derivative as well as preparation method, pharmaceutical composition and application thereof". Paragraph 0039-0043. . Retrieved 2021/09/21.
• 4、 -. "NOVEL FULLY SYNTHETIC AND SEMISYNTHETIC PLEUROMUTILIN DERIVATIVES AS NEW ANTIBIOTICS AND THEIR PREPARATION". Page/Page column 44; 115-116. . Retrieved 2019/10/19.