![(3aR,4R,5R,7S,8S,9R,9aS,12R)-8-hydroxy-4,7,9,12-tetramethyl-3-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl 2-(tosyloxy)acetate](https://ecdn6-nc.globalso.com/upload/p/4509/image_other/2026-05/4-chloro-3-methyl-1-2-benzenediamine-hydrochloride.png)
(3aR,4R,5R,7S,8S,9R,9aS,12R)-8-hydroxy-4,7,9,12-tetramethyl-3-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl 2-(tosyloxy)acetate
Basic Information
product Description
(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyl-5-hydroxy-4,6,9,10-tetramethyl-1-oxodecahydro-3a,9-propano-3aH-cyclopentacycloocten-8-yl[[(4-methylphenyl)sulfonyl]oxy]acetate (Pleuromutilin 22-Tosylate, CAS 31716-01-5), with molecular formula C₂₉H₄₀O₇S and molecular weight 532.69, is a core parent nucleus intermediate for the synthesis of pleuromutilin antibiotics (including Tiamulin, Lefamulin Acetate, etc.), and a key impurity reference standard in Tiamulin quality control (EP Impurity L/USP Related Compound A). It is characterized by natural pleuromutilin parent nucleus skeleton, 8 precisely fixed chiral centers and active leaving group, serving as a critical node connecting parent nucleus purification and side chain modification.
Derived from natural pleuromutilin via esterification of the 22-hydroxy group with tosyl chloride, this intermediate has exactly the same configuration of 8 chiral centers as the natural product, ensuring the biological activity of downstream APIs. The 5-hydroxy group and 1-ketone group on the parent nucleus are stable structural groups, the 6-vinyl group is a subsequent modification site, and the 2-(tosyloxy)acetyl group linked at the 22-position is the core active leaving group. This group can leave rapidly under mild nucleophilic conditions, providing sites for coupling reactions with side chains (sulfur-containing, amino-containing and other chiral fragments), and the coupling process will not destroy the chiral configuration of the parent nucleus, meeting the precise synthesis requirements of pleuromutilin antibiotics.
In terms of physicochemical properties, it appears as white to off-white crystalline powder, easily soluble in medium-polar organic solvents such as dichloromethane, tetrahydrofuran, ethyl acetate and toluene, slightly soluble in methanol and ethanol, and poorly soluble in water. It has excellent stability under room temperature and dry conditions, with ketone and hydroxyl groups not prone to side reactions. High temperature (> 100℃), strong acidic conditions and strong nucleophiles should be avoided to prevent premature leaving of the tosylate group or isomerization of the parent nucleus chiral configuration.
For applications, it is mainly used in the synthesis of pleuromutilin antibiotics such as Tiamulin and Lefamulin Acetate. The chiral configuration of its parent nucleus directly determines the binding efficiency of APIs to bacterial ribosomes, which is the structural basis of antibacterial activity. Meanwhile, as a key impurity reference standard in Tiamulin quality control, it is used for quality control during drug production to ensure drug safety and efficacy. In addition, it can serve as a parent nucleus platform for the R&D of novel pleuromutilin antibiotics, adapting to the structural modification needs of drugs with different antibacterial spectra.
For industrial application, extremely strict purity requirements are needed. As a synthetic intermediate, chemical purity ≥ 99% and chiral purity (ee value) ≥ 99.5% are required; as an impurity reference standard, purity ≥ 97% is required, meeting EP/USP standards. It should be sealed and stored in a refrigerated environment at 0-8℃, protected from light, isolated from air and nucleophiles, and stored separately to prevent configuration isomerization or deterioration of active groups, ensuring the conversion rate of subsequent synthesis reactions and the accuracy of API quality control.
product Specification
|
Item |
Unit |
Specification |
|
Appearance |
|
white to off-white crystalline powder |
|
Solubility |
|
easily soluble in medium-polar organic solvents such as dichloromethane, tetrahydrofuran, ethyl acetate and toluene, slightly soluble in methanol and ethanol, and poorly soluble in water. |
|
Identification |
|
infrared spectroscopy + HPLC retention time |
|
Other impurities |
% |
≤0.1 |
|
Related Substances - Total Impurities |
% |
≤1.0 |
|
Main peak purity |
% |
≥99.0 |
|
Chiral Purity |
% |
≥99.5 |
|
Storage |
|
sealed and stored in a refrigerated environment at 0-8℃ |
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