The synthesis of complex pharmaceutical compounds often relies on specialized intermediates that possess precise chemical structures and high purity. For the widely prescribed cholesterol-lowering drug Atorvastatin Calcium, (4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate, identified by CAS number 125971-94-0, is a pivotal intermediate. This article provides an overview of its chemical properties, manufacturing considerations, and its indispensable role in pharmaceutical production.

Chemical Identity and Properties

(4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate is a chiral molecule with the molecular formula C14H23NO4 and a molecular weight of approximately 269.34. Its chemical name accurately describes its structure: a dioxane ring system with specific substitutions, including a cyanomethyl group and a tert-butyl ester. Key physical properties reported by manufacturers include:

  • Appearance: Typically a white to off-white or light yellow crystalline powder.
  • Assay: High purity is critical, with specifications usually set at ≥99.5%.
  • Melting Point: Commonly reported in the range of 65-69°C.
  • Solubility: Soluble in common organic solvents like chloroform, facilitating its use in synthesis.
  • Optical Activity: Its chiral nature is confirmed by specific optical rotation measurements, e.g., [α]20/D 1.0°, c = 1 in chloroform.

Manufacturing and Synthesis

The synthesis of this intermediate typically involves advanced chemical processes to ensure the correct stereochemistry. One common synthetic route involves the reaction of sodium cyanide with a precursor like (4R-cis)-6-Chloromethyl-2,2-dimethyl-1,3-dioxane-4-acetic Acid tert-Butyl Ester. Manufacturers invest in precise reaction control, purification techniques (like crystallization), and rigorous quality testing to achieve the required pharmaceutical grade. Companies producing this intermediate often operate under stringent quality management systems, including GMP certification, to meet the demands of the pharmaceutical industry.

Critical Application in Atorvastatin Synthesis

The primary and most significant application of (4R,6R)-tert-Butyl-6-cyanomethyl-2,2-dimethyl-1,3-dioxane-4-acetate is as a direct precursor in the synthesis of Atorvastatin Calcium. Atorvastatin is a statin, a class of drugs used to lower blood cholesterol levels, particularly LDL cholesterol, and reduce the risk of cardiovascular disease. The specific structure of this intermediate provides the necessary chiral center and functional groups that are elaborated in subsequent steps to form the final Atorvastatin molecule. Its role is pivotal in constructing the heptanoic acid side chain, a key component for the drug's HMG-CoA reductase inhibitory activity.

Sourcing Considerations for Pharmaceutical Companies

When pharmaceutical companies seek to buy this intermediate, they look for suppliers who can guarantee consistent quality, reliable availability, and competitive pricing. Manufacturers with strong technical support, comprehensive documentation (SDS, TDS, CoA), and adherence to international standards are preferred. Understanding the supplier's manufacturing processes and quality control protocols is essential for ensuring the integrity of the final API. Proactive engagement with reputable manufacturers, including those in China, can secure a stable supply chain for this indispensable pharmaceutical intermediate.