(2S)-2-Hydroxypent-4-ynoic Acid (CAS 194864-96-5): A Versatile Chiral Building Block in Advanced Organic Synthesis
(2S)-2-hydroxypent-4-ynoic acid (Molecular Formula: C₅H₆O₃, MW: 114.1), recognized by its
CAS number 194864-96-5, is a highly functionalized chiral intermediate
characterized by two distinct reactive moieties: a terminal alkyne and an α-hydroxy acid group. This unique structural combination
makes it an indispensable scaffold in the asymmetric synthesis of complex
natural products, specialized pharmaceuticals, and bio-orthogonal chemical
probes.
Finetech Industry limited provide high-purity
(2S)-2-hydroxypent-4-ynoic acid synthesized under rigorous quality control
standards to ensure optical purity and chemical stability for demanding
research applications.
Core Applications and Synthetic Utility
1. Click Chemistry and Bio-orthogonal Labeling
The terminal alkyne group in (2S)-2-hydroxypent-4-ynoic acid allows
for seamless integration into Copper-catalyzed Azide-Alkyne Cycloaddition
(CuAAC), commonly known as "click chemistry." Researchers utilize
this compound to introduce chiral hydroxy-acid motifs into biomolecules,
facilitating the study of protein-ligand interactions and the development of
targeted drug delivery systems.
2. Synthesis of Chiral Polyheterocycles
The α-hydroxy acid functionality serves
as a precursor for various intramolecular cyclizations. Literature in The
Journal of Organic Chemistry highlights the use of similar chiral pentynoic
acid derivatives in the construction of α-methylene-γ-butyrolactones, a structural motif
prevalent in numerous bioactive sesquiterpene lactones known for their
anti-inflammatory and anti-tumor properties.
3. Intermediate for Peptidomimetics
In the field of medicinal chemistry, (2S)-2-hydroxypent-4-ynoic acid
is employed to create non-natural amino acid analogues. By substituting the
hydroxy group or utilizing it for esterification/amidation, chemists can
synthesize peptidomimetics with restricted conformations, improving the
metabolic stability of peptide-based therapeutics.
Academic References and Research Context
The chemical behavior and synthetic potential of (2S)-2-hydroxypent-4-ynoic
acid are supported by extensive research in asymmetric catalysis and
natural product total synthesis:
- Asymmetric
Induction: Tetrahedron:
Asymmetry provides foundational methodologies for the preparation of
chiral $\alpha$-hydroxy acids, emphasizing the importance of high
enantiomeric excess (ee) for the bioactivity of final drug candidates.
- Alkyne
Reactivity: Angewandte Chemie
documents the utility of terminal alkynes in transition-metal catalyzed
cross-coupling reactions (e.g., Sonogashira coupling), where this compound
acts as a rigid, functionalized linker.
- Metabolic
Studies: Data available via PubChem
(Compound CID: 96495375) and ChemicalBook underscore its
physicochemical properties, confirming its stability as a solid-state
intermediate for industrial-scale manufacturing.
Technical Specifications (Finetech Industry limited)
|
Property |
Value |
|
IUPAC Name |
(2S)-2-hydroxypent-4-ynoic
acid |
|
CAS Number |
|
|
Molecular Weight |
114.1 g/mol |
|
Purity |
95% |
|
EE |
99% |
|
Appearance |
Solid |
Strategic Sourcing from Finetech Industry limited
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Industry limited ensures that all batches of CAS 194864-96-5 are
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- Title: (2S)-2-Hydroxypent-4-ynoic acid (CAS
194864-96-5) | Synthetic Utility & Research
- Description: Explore the
applications of (2S)-2-Hydroxypent-4-ynoic acid in click chemistry and
chiral synthesis. High-purity CAS 194864-96-5 available at finetech
Industry limited.
- Keywords: CAS 194864-96-5, (2S)-2-hydroxypent-4-ynoic
acid, Chiral building blocks, Alpha-hydroxy acids, Finetech Industry
limited.