The Chemical Profile of Methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate and its Synthetic Utility
Methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate, identified by its CAS number 147118-35-2, is a complex organic molecule with significant utility in synthetic chemistry, particularly as a key intermediate in the pharmaceutical industry. Its detailed chemical profile, including its molecular formula (C31H39O4PSi) and molecular weight (534.69800), provides foundational data for its application in intricate synthesis pathways.
The structure of this compound features a silyloxy group protecting a hydroxyl function, a ketone, and a triphenylphosphoranylidene moiety. These functional groups are strategically placed to participate in specific chemical transformations. The presence of the chiral center at the R position is crucial, as it dictates the stereochemistry of the final drug product, Rosuvastatin. Understanding the synthesis and handling of this chiral intermediate, such as the specific optical rotation values typically between -5.2º to -7.2º, is vital for maintaining enantiomeric purity.
The triphenylphosphoranylidene group, often derived from a Wittig reaction precursor, is a hallmark of its synthetic utility. This functional group can participate in various olefination reactions, forming carbon-carbon double bonds with high stereoselectivity, which is a common requirement in the synthesis of complex pharmaceutical molecules. The physical characteristics, such as its appearance as a white or light yellow crystalline powder and a melting point range of 77.5-78.5°C, are important parameters for identifying and qualifying the substance.
As a prominent rosuvastatin intermediate, its role in the multi-step synthesis of Rosuvastatin is well-documented. It efficiently contributes a significant portion of the final drug's carbon backbone, incorporating necessary functional groups and stereochemistry. The efficiency of the synthesis directly correlates with the quality and reactivity of the methyl 3r 3 tert butyldimethylsilyloxy 5 oxo 6 triphenylphosphoranylidenehexanoate used. Therefore, manufacturers who focus on obtaining this compound from reliable methyl 3r 3 tert butyldimethylsilyloxy 5 oxo 6 triphenylphosphoranylidenehexanoate suppliers often experience smoother production processes and higher yields.
Researchers also investigate the cas 147118-35-2 properties to explore its potential in synthesizing other complex organic molecules or novel drug candidates. The purity of the compound, typically above 98.0%, is critical for ensuring reproducible experimental results and avoiding side reactions that could lead to unwanted byproducts, such as tracing rosuvastatin impurity 171.
In essence, Methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate is a testament to the power of precise organic synthesis. Its well-defined chemical profile and proven synthetic utility make it an indispensable component in the modern pharmaceutical manufacturing landscape, underpinning the production of essential medicines like Rosuvastatin.
Perspectives & Insights
Quantum Pioneer 24
“Methyl (3R)-3-(tert-butyldimethylsilyloxy)-5-oxo-6-triphenylphosphoranylidenehexanoate, identified by its CAS number 147118-35-2, is a complex organic molecule with significant utility in synthetic chemistry, particularly as a key intermediate in the pharmaceutical industry.”
Bio Explorer X
“Its detailed chemical profile, including its molecular formula (C31H39O4PSi) and molecular weight (534.”
Nano Catalyst AI
“69800), provides foundational data for its application in intricate synthesis pathways.”