Cas no 152786-10-2 ((2R,3R)-2-Amino-3-methylpentan-1-ol)

(2R,3R)-2-Amino-3-methylpentan-1-ol is a chiral amino alcohol with a defined stereochemistry, making it valuable for asymmetric synthesis and pharmaceutical applications. Its structure features both amino and hydroxyl functional groups, enabling its use as a versatile building block in organic synthesis. The (2R,3R) configuration ensures high enantioselectivity in reactions, particularly in the preparation of biologically active compounds. This compound’s stability and well-characterized properties make it suitable for use as a ligand or intermediate in catalytic processes. Its purity and stereochemical consistency are critical for researchers requiring precise control over reaction outcomes in medicinal chemistry and fine chemical synthesis.
(2R,3R)-2-Amino-3-methylpentan-1-ol structure
152786-10-2 structure
Product Name:(2R,3R)-2-Amino-3-methylpentan-1-ol
CAS No:152786-10-2
MF:C6H15NO
MW:117.189401865005
MDL:MFCD00270273
CID:4727412
Update Time:2025-06-08

(2R,3R)-2-Amino-3-methylpentan-1-ol Chemical and Physical Properties

Names and Identifiers

    • (2R,3R)-2-Amino-3-methylpentan-1-ol
    • D-(-)-Isoleucinol
    • D-Isoleucinol
    • FCH841023
    • API0002182
    • AX8018084
    • MDL: MFCD00270273
    • Inchi: 1S/C6H15NO/c1-3-5(2)6(7)4-8/h5-6,8H,3-4,7H2,1-2H3/t5-,6+/m1/s1
    • InChI Key: VTQHAQXFSHDMHT-RITPCOANSA-N
    • SMILES: OC[C@@H]([C@H](C)CC)N

Computed Properties

  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 8
  • Rotatable Bond Count: 3
  • Complexity: 56.5
  • Topological Polar Surface Area: 46.2

(2R,3R)-2-Amino-3-methylpentan-1-ol Pricemore >>

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Additional information on (2R,3R)-2-Amino-3-methylpentan-1-ol

Chemical Profile of (2R,3R)-2-Amino-3-methylpentan-1-ol (CAS No. 152786-10-2)

(2R,3R)-2-Amino-3-methylpentan-1-ol, identified by its Chemical Abstracts Service number CAS No. 152786-10-2, is a chiral amino alcohol with significant applications in the field of pharmaceutical chemistry and biotechnology. This compound, characterized by its specific stereochemical configuration, has garnered attention due to its potential role in the synthesis of biologically active molecules and its utility in drug development pipelines.

The molecular structure of (2R,3R)-2-Amino-3-methylpentan-1-ol consists of a five-carbon chain with an amine group at the second carbon and a methyl group at the third carbon, both arranged in a specific stereochemical orientation. This configuration makes it a valuable building block for constructing more complex molecules, particularly those requiring precise stereochemical control. The compound's ability to serve as a stereocenter precursor is highly advantageous in medicinal chemistry, where enantiomeric purity often dictates the efficacy and safety of therapeutic agents.

In recent years, there has been growing interest in the development of enantioselective synthetic methodologies to produce optically active compounds like (2R,3R)-2-Amino-3-methylpentan-1-ol. Advances in asymmetric catalysis and biocatalysis have enabled more efficient and sustainable routes to chiral intermediates. For instance, enzymatic resolutions and dynamic kinetic resolutions have been employed to achieve high enantiomeric excesses with minimal environmental impact. These innovations align with the broader trend toward green chemistry principles, emphasizing the need for sustainable synthetic strategies in pharmaceutical manufacturing.

The pharmaceutical industry has leveraged (2R,3R)-2-Amino-3-methylpentan-1-ol as a key intermediate in the synthesis of various therapeutic agents. Its structural features make it a versatile scaffold for designing molecules with specific biological activities. Notably, derivatives of this compound have been explored for their potential in modulating enzyme inhibition and receptor binding. Such applications are particularly relevant in the treatment of neurological disorders, where precise stereochemical control can significantly influence drug efficacy and side effect profiles.

Recent research has highlighted the role of chiral amino alcohols like (2R,3R)-2-Amino-3-methylpentan-1-ol in the development of protease inhibitors. Proteases are enzymes that play crucial roles in numerous physiological processes, and their inhibition is often a key strategy in anti-inflammatory and antiviral therapies. By incorporating stereogenic centers derived from this compound into drug candidates, researchers have been able to design molecules that exhibit enhanced binding affinity and selectivity. This approach has led to promising candidates entering clinical trials for conditions such as HIV infection and cancer.

The synthesis of complex natural products also benefits from the use of intermediates like (2R,3R)-2-Amino-3-methylpentan-1-ol. Many bioactive compounds found in plants and microorganisms possess intricate stereochemical architectures that are challenging to replicate synthetically. The availability of readily accessible chiral building blocks simplifies these synthetic endeavors, allowing chemists to focus on optimizing yield and purity rather than developing novel catalytic systems from scratch. This underscores the importance of well-characterized intermediates in advancing synthetic organic chemistry.

In addition to its pharmaceutical applications, (2R,3R)-2-Amino-3-methylpentan-1-ol has found utility in materials science and industrial processes. Its unique chemical properties make it suitable for use as a chiral auxiliary or ligand in catalytic systems. Researchers have demonstrated its effectiveness in promoting asymmetric reactions under mild conditions, which is critical for large-scale industrial applications where energy efficiency and environmental considerations are paramount.

The future prospects for (2R,3R)-2-Amino-3-methylpentan-1-ol are promising, given its versatility and the ongoing advancements in synthetic methodologies. As the demand for enantiomerically pure compounds grows, so does the need for efficient and scalable production methods. Innovations such as flow chemistry and continuous manufacturing are likely to play a significant role in enhancing the accessibility of this valuable intermediate. Furthermore, collaborations between academia and industry will continue to drive new applications and refine existing synthetic routes.

In conclusion, (2R,3R)-2-Amino-3-methylpentan-1-ol (CAS No. 152786-10-2) represents a cornerstone compound in modern chemical synthesis. Its stereochemical precision makes it indispensable for constructing biologically active molecules, while its adaptability allows for diverse applications across multiple industries. As research progresses and new methodologies emerge, the significance of this compound is expected to grow further, solidifying its place as a key player in both academic research and industrial innovation.

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