Cas no 368866-32-4 (methyl (2S)-2-amino-2-(oxan-4-yl)acetate)

Methyl (2S)-2-amino-2-(oxan-4-yl)acetate is a chiral ester derivative featuring an amino group and a tetrahydropyran (oxane) moiety. Its stereospecific (S)-configuration makes it a valuable intermediate in asymmetric synthesis, particularly for pharmaceutical applications requiring enantioselective building blocks. The oxan-4-yl group enhances solubility and stability, while the methyl ester functionality allows for further derivatization under mild conditions. This compound is useful in peptidomimetics and bioactive molecule development due to its structural versatility. High purity and well-defined stereochemistry ensure reproducibility in research and industrial processes. Its balanced lipophilicity and reactivity profile make it suitable for medicinal chemistry and catalyst design.
methyl (2S)-2-amino-2-(oxan-4-yl)acetate structure
368866-32-4 structure
Product Name:methyl (2S)-2-amino-2-(oxan-4-yl)acetate
CAS No:368866-32-4
MF:C8H15NO3
MW:173.209602594376
MDL:MFCD06796165
CID:297584
PubChem ID:45789912
Update Time:2025-05-25

methyl (2S)-2-amino-2-(oxan-4-yl)acetate Chemical and Physical Properties

Names and Identifiers

    • (S)-Methyl 2-amino-2-(tetrahydro-2H-pyran-4-yl)acetate
    • (S)-Amino-(tetrahydro-pyran-4-yl)-acetic acid methyl ester
    • (S)-AMINO-(TETRAHYDROPYRAN-4-YL)ACETIC ACID METHYL ESTER,
    • 2H-Pyran-4-acetic acid,a-aminotetrahydro-, methyl ester,(aS)-
    • (S)-AMINO(TETRAHYDROPYRAN-4-YL)ACETIC ACID METHYL ESTER
    • (S)-pyranylglycine methyl ester
    • AG-F-28987
    • AK-34886
    • ANW-74685
    • CTK4H7331
    • SureCN903766
    • methyl (2S)-2-amino-2-(oxan-4-yl)acetate
    • DTXSID20672102
    • Methyl (2S)-amino(oxan-4-yl)acetate
    • (S)-Methyl2-amino-2-(tetrahydro-2H-pyran-4-yl)acetate
    • AKOS006292894
    • A823431
    • 368866-32-4
    • F31386
    • SCHEMBL903766
    • MDL: MFCD06796165
    • Inchi: 1S/C8H15NO3/c1-11-8(10)7(9)6-2-4-12-5-3-6/h6-7H,2-5,9H2,1H3/t7-/m0/s1
    • InChI Key: GLXVKVOENRRZDF-ZETCQYMHSA-N
    • SMILES: O1CCC([C@@H](C(=O)OC)N)CC1

Computed Properties

  • Exact Mass: 173.10525
  • Monoisotopic Mass: 173.105
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 3
  • Complexity: 154
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 61.6A^2
  • XLogP3: -0.2

Experimental Properties

  • Density: 1.104
  • Boiling Point: 244.1°C at 760 mmHg
  • Flash Point: 94.5°C
  • Refractive Index: 1.471
  • PSA: 61.55
  • LogP: 0.61360

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Additional information on methyl (2S)-2-amino-2-(oxan-4-yl)acetate

Introduction to Methyl (2S)-2-amino-2-(oxan-4-yl)acetate (CAS No. 368866-32-4)

Methyl (2S)-2-amino-2-(oxan-4-yl)acetate, a compound with the chemical identifier CAS No. 368866-32-4, is a significant molecule in the field of pharmaceutical chemistry and biochemistry. This compound, characterized by its unique stereochemistry and functional groups, has garnered considerable attention due to its potential applications in drug development and synthetic biology. The presence of the (2S) configuration and the oxan-4-yl moiety makes it a versatile intermediate in the synthesis of more complex molecules, particularly in the realm of chiral drugs.

The stereochemical purity of Methyl (2S)-2-amino-2-(oxan-4-yl)acetate is crucial for its biological activity. In recent years, there has been a growing emphasis on the development of enantiomerically pure compounds to enhance therapeutic efficacy while minimizing side effects. The (S)-configuration of this compound has been shown to exhibit superior biological properties compared to its (R)-enantiomer, making it a valuable building block for pharmacological research.

Recent studies have highlighted the importance of Methyl (2S)-2-amino-2-(oxan-4-yl)acetate in the synthesis of novel therapeutic agents. For instance, researchers have utilized this compound as a precursor in the development of new antibiotics and anti-inflammatory drugs. The oxan-4-yl group, which is part of the tetrahydropyran ring, contributes to the compound's solubility and bioavailability, making it an attractive candidate for oral administration.

In addition to its pharmaceutical applications, Methyl (2S)-2-amino-2-(oxan-4-yl)acetate has found utility in synthetic organic chemistry. Its structural features allow for facile modifications, enabling chemists to explore diverse chemical pathways. This flexibility has been exploited in the synthesis of complex natural products and in the development of new synthetic methodologies.

The chemical properties of Methyl (2S)-2-amino-2-(oxan-4-yl)acetate make it a valuable reagent in peptide synthesis. The amino group and the ester functionality provide multiple points of attachment for other biomolecules, facilitating the construction of peptide chains with precise stereochemistry. This has significant implications for drug design, particularly in the development of peptidomimetics that mimic the biological activity of natural peptides.

Advances in computational chemistry have further enhanced the understanding of Methyl (2S)-2-amino-2-(oxan-4-yl)acetate's reactivity and interactions. Molecular modeling studies have revealed insights into how this compound interacts with biological targets, providing a foundation for rational drug design. These computational approaches have been instrumental in predicting binding affinities and optimizing lead compounds for clinical trials.

The role of Methyl (2S)-2-amino-2-(oxan-4-yl)acetate in medicinal chemistry extends beyond its use as an intermediate. It has also been investigated for its potential role as a chiral auxiliary in asymmetric synthesis. The ability to selectively induce stereoselectivity in reactions using this compound has opened new avenues for synthesizing enantiomerically pure compounds efficiently.

In conclusion, Methyl (2S)-2-amino-2-(oxan-4-yl)acetate is a multifaceted compound with significant applications in pharmaceuticals and synthetic chemistry. Its unique structural features and stereochemical purity make it a valuable tool for researchers aiming to develop novel therapeutic agents and synthetic methodologies. As our understanding of molecular interactions continues to evolve, compounds like Methyl (2S)-2-amino-2-(oxan-4-y acetate will undoubtedly play a crucial role in advancing scientific discovery.

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