Cas no 935837-51-7 (methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate)

Methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate is a chiral pyrrolidine derivative with significant utility in asymmetric synthesis and pharmaceutical applications. Its stereochemically defined structure, featuring both (2S) and (4R) configurations, makes it a valuable building block for the preparation of enantiomerically pure compounds. The tert-butoxy group enhances steric protection, improving stability during synthetic transformations, while the methyl ester functionality offers versatility for further derivatization. This compound is particularly useful in the synthesis of bioactive molecules, including peptidomimetics and protease inhibitors, where precise stereocontrol is critical. Its high purity and well-defined stereochemistry ensure reproducibility in complex synthetic routes.
methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate structure
935837-51-7 structure
Product Name:methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate
CAS No:935837-51-7
MF:C10H19NO3
MW:201.262763261795
CID:4720506
PubChem ID:15030755
Update Time:2025-05-20

methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate Chemical and Physical Properties

Names and Identifiers

    • (2s,4r)-methyl 4-tert-butoxypyrrolidine-2-carboxylate
    • (2S,4R)-4-t-Butoxyproline methyl ester
    • methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate
    • Inchi: 1S/C10H19NO3/c1-10(2,3)14-7-5-8(11-6-7)9(12)13-4/h7-8,11H,5-6H2,1-4H3/t7-,8+/m1/s1
    • InChI Key: LDIDWWQVKCXFHH-SFYZADRCSA-N
    • SMILES: O(C(C)(C)C)[C@H]1CN[C@H](C(=O)OC)C1

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 4
  • Complexity: 210
  • Topological Polar Surface Area: 47.6

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Additional information on methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate

Methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate: A Comprehensive Overview

Methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate, with the CAS number 935837-51-7, is a compound of significant interest in the fields of organic chemistry and pharmacology. This compound is characterized by its unique stereochemistry and functional groups, which make it a valuable tool in various research and industrial applications. The molecule consists of a pyrrolidine ring with specific substituents: a tert-butoxy group at the 4-position and a methyl ester at the 2-position. The stereochemistry at the 2S and 4R positions is critical for its biological activity and synthetic utility.

The synthesis of methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate involves a series of carefully designed reactions to achieve the desired stereochemistry. Recent advancements in asymmetric synthesis have enabled researchers to construct this compound with high enantiomeric excess, leveraging techniques such as organocatalysis and transition metal-catalyzed reactions. These methods not only enhance the efficiency of synthesis but also contribute to the sustainability of chemical processes, aligning with current trends in green chemistry.

One of the most notable applications of methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate is in drug discovery. The compound serves as a versatile building block for constructing bioactive molecules. For instance, it has been employed in the development of inhibitors for various enzymes, including kinases and proteases. Recent studies have demonstrated its potential as a lead compound in anti-cancer drug design, where it exhibits selective activity against cancer cell lines while showing reduced toxicity to normal cells.

In addition to its role in therapeutic development, methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate has found applications in materials science. Its ability to form stable amide bonds makes it an attractive candidate for polymer synthesis. Researchers have explored its use in creating biodegradable polymers for biomedical applications, such as drug delivery systems and tissue engineering scaffolds. These polymers exhibit excellent biocompatibility and controlled degradation profiles, which are essential for advanced medical devices.

The stereochemical properties of methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate also make it a valuable substrate for studying enzyme mechanisms. Enzymologists have utilized this compound to investigate the stereoselectivity of various hydrolases and transferases. Recent findings have provided insights into the catalytic processes involved in asymmetric catalysis, paving the way for the development of more efficient biocatalysts.

From an analytical standpoint, methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate has been extensively studied using modern spectroscopic techniques such as NMR and mass spectrometry. These studies have not only confirmed its structural integrity but also provided valuable data on its conformational flexibility and intermolecular interactions. Such information is crucial for understanding its behavior in different chemical environments and optimizing its use in various applications.

In conclusion, methyl (2S,4R)-4-(tert-butoxy)pyrrolidine-2-carboxylate is a multifaceted compound with significant implications across diverse scientific disciplines. Its unique structure, coupled with advancements in synthetic methodologies and analytical techniques, positions it as a key player in contemporary research efforts. As ongoing studies continue to uncover new applications and mechanisms involving this compound, its importance in both academic and industrial settings is expected to grow further.

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