(1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carboxamide methanesulfonate
(1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carboxamide methanesulfonate, identified by CAS number 709031-45-8, is a specialized organic building block and a significant chiral intermediate in the field of medicinal chemistry and fine chemical synthesis. Structurally, it consists of a bicyclic 2-azabicyclo[3.1.0]hexane framework featuring a carboxamide functional group, stabilized as a methanesulfonate salt. This specific stereoisomer is characterized by its rigid bicyclic architecture, which provides a unique spatial orientation essential for high-affinity molecular interactions in biological systems. As a crystalline solid, it exhibits favorable stability and solubility profiles suitable for large-scale chemical processing. In industrial and research settings, this compound serves as a critical precursor for the synthesis of complex pharmaceutical agents, particularly those targeting metabolic pathways. Its production involves precise stereoselective synthesis to maintain the integrity of its three chiral centers, making it a high-value reagent for advanced chemical manufacturing and drug development projects requiring rigid proline-like scaffolds.
• Pharmaceutical Synthesis: The primary application of CAS 709031-45-8 is as a key intermediate in the synthesis of dipeptidyl peptidase-4 (DPP-4) inhibitors. Its rigid bicyclic structure is a core component of molecules like Saxagliptin, where it mimics the proline residue but with increased conformational constraint, enhancing the potency and selectivity of the final therapeutic molecule.
• Chiral Building Block: It serves as a versatile chiral scaffold in organic synthesis. Researchers utilize this compound to introduce the (1S,3S,5S)-2-azabicyclo[3.1.0]hexane moiety into diverse molecular frameworks. This is particularly useful in the development of peptidomimetics and other small molecules where precise spatial arrangement of functional groups is required to achieve specific chemical properties.
• Process Development and Optimization: In industrial chemistry, this methanesulfonate salt is employed in the optimization of synthetic routes for complex heterocyclic compounds. Its stability as a mesylate salt facilitates easier handling, purification, and storage compared to the free base, making it an ideal candidate for standardized manufacturing protocols and quality-controlled chemical production.
• Medicinal Chemistry Research: Beyond its role in established drug synthesis, the compound is a valuable tool in lead optimization and SAR (Structure-Activity Relationship) studies. It allows medicinal chemists to explore the effects of constrained amino acid analogues on protein-ligand binding, contributing to the discovery of novel inhibitors across various therapeutic areas.
Product Name: (1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carboxamide methanesulfonate
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