60924-38-1

Basic information

• Product Name: 2-[(Methylsulfonyl)oxy]acetic acid (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester
• Synonyms: 2-[(Methylsulfonyl)oxy]acetic acid (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester;Pleuromutilin-22-mesylate;RetapaMulin I;Pleuromutilin methanesulfonate;(3AS,4S,5S,7R,8R,9S,9aR,12R)-8-hydroxy-4,7,9,12-tetramethyl-3-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl 2-((methylsulfonyl)oxy)acetate
• CAS NO: 60924-38-1
• Molecular Formula: C₂₃H₃₆O₇S
• Molecular Weight: 456.59
• Mol File: 60924-38-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 571 °C at 760 mmHg
• Flash Point: 299.1 °C
• Appearance: /
• Density: 1.22
• Refractive Index: 1.537
• Storage Temp.: 2-8°C
• PKA: 14.63±0.70(Predicted)
• CAS DataBase Reference: 2-[(Methylsulfonyl)oxy]acetic acid (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(Methylsulfonyl)oxy]acetic acid (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester(60924-38-1)
• EPA Substance Registry System: 2-[(Methylsulfonyl)oxy]acetic acid (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl ester(60924-38-1)

Safety Data

• Hazardous Substances Data: 60924-38-1(Hazardous Substances Data)

Usage

Uses

Pleuromutilin 22-Mesylate is a derivative of Pleuroutillin (P610500), an antibiotic substance produced by the basidiomycetes Pleurotus mutilus used in the synthesis of Retapamulin (R279008), an antibacterial agent used as a substitute for the more commonly known Penicillin (P223505).

InChI:InChI=1/C23H36O7S/c1-7-21(4)12-17(30-18(25)13-29-31(6,27)28)22(5)14(2)8-10-23(15(3)20(21)26)11-9-16(24)19(22)23/h7,14-15,17,19-20,26H,1,8-13H2,2-6H3/t14-,15+,17-,19+,20+,21-,22+,23+/m1/s1

Upstream product

• 1212267-35-0 8-glycoloyloxy-5-hydroxy-4,6,9,10-tetramethyl-6-vinyl-octahydro-3a,9-propano-cyclopentacycloocten-1-one 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 224296-26-8 (3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl-[1-azoniabicyclo[2.2.2]octane-4-thio]acetate 
• 224452-66-8 retapamulin 

Relevant articles and documents

ANTIBACTERIAL AND ANTIFUNGAL PLEUROMUTILIN CONJUGATES

Compounds of formula (1) comprising a pleuromutilin backbone with a triazole based side-group at C22 are provided. The compounds can be used for treatment of bacterial infections and fungal infections. Importantly, infections caused by multidrug-resistant

Synthesis of the pleuromutilin antibiotic SB-268091: A new practical and efficient synthesis of quinuclidine-4-thiol

A synthesis of the pleuromutilin antibiotic SB-268091 is described which includes a new and improved route to the quinuclidine-4-thiol ligand. This chemistry has been run on multikilo scale and involved a reductive double debenzylation using sodium in liquid ammonia. Alternative conditions have been developed to prepare quinuclidine-4-thiol which avoid the use of sodium in liquid ammonia. The generality of this process to prepare differentially S-protected quinuclidine-4-thiols is also discussed and exemplified by the preparation of a range of analogues.

Process for the preparation of Retapamulin and its intermediates

Processes for preparing tropine derivatives of the following Formula B are provided where LG represents a leaving group. The tropine derivatives may be used to prepare Retapamulin, preferably in substantially pure form. Also provided are processes for preparing Retapamulin comprising combining a base, tropine thiol in a free base or salt form, an organic solvent, and a pleuromutilin derivative of Formula A: