(3S,4R)-4-aminooxan-3-ol hydrochloride
[CAS# 1630815-44-9]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound
• Name: (3S,4R)-4-aminooxan-3-ol hydrochloride
• Molecular Formula: C₅H₁₂ClNO₂
• Molecular Weight: 153.61
• CAS Registry Number: 1630815-44-9
• EC Number: 976-227-2
• SMILES: C1COC[C@H]([C@@H]1N)O.Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

(3S,4R)-4-Aminooxan-3-ol hydrochloride is a stereochemically defined, water-soluble organic salt composed of a chiral amino alcohol functionalized tetrahydropyran ring and hydrochloric acid. The parent compound, (3S,4R)-4-aminooxan-3-ol, features two stereogenic centers within a six-membered oxygen-containing ring (oxane), bearing a hydroxyl group at the 3-position and an amino group at the 4-position. These functional groups and the ring conformation make this molecule a valuable intermediate in pharmaceutical and synthetic organic chemistry.

The hydrochloride form results from the protonation of the primary amine group with hydrochloric acid, yielding a crystalline salt with enhanced stability, solubility, and ease of handling. Salts of this type are frequently employed in medicinal chemistry to facilitate compound formulation and improve pharmacokinetic properties.

The discovery and utilization of oxane derivatives like (3S,4R)-4-aminooxan-3-ol can be traced back to broader research on chiral building blocks for the construction of biologically active molecules. The tetrahydropyran scaffold is common in natural products and synthetic drugs, contributing to bioactivity through its conformational rigidity and potential for hydrogen bonding. Amino alcohols, in particular, are key motifs in antiviral agents, β-lactamase inhibitors, and other therapeutic classes.

Synthetically, (3S,4R)-4-aminooxan-3-ol can be obtained through stereoselective transformations involving dihydroxylated precursors or epoxide opening reactions. Enzymatic resolution or asymmetric catalysis may also be used to access the (3S,4R)-diastereomer selectively. The hydrochloride salt is typically formed by treatment with anhydrous hydrogen chloride in ethanol or another suitable solvent, followed by crystallization.

This compound serves as an intermediate in the synthesis of various heterocyclic and peptidomimetic compounds. Its amino and hydroxyl functionalities allow it to participate in a range of reactions, including amide coupling, acylation, and cyclization, often under mild conditions. Because of its stereochemistry and reactivity, it is particularly valuable in synthesizing enantiomerically pure drug candidates.

In medicinal chemistry, derivatives of 4-aminooxan-3-ol have been investigated for their potential as enzyme inhibitors and as scaffolds in small molecule libraries targeting neurological, infectious, and metabolic diseases. The stereochemical configuration plays a crucial role in determining the biological activity of such molecules, influencing both binding affinity and specificity for their molecular targets.

Additionally, this compound can be incorporated into complex structures to modulate solubility and metabolic stability. The oxane ring is resistant to hydrolysis under physiological conditions, while the presence of polar substituents like the hydroxyl and amino groups aids in aqueous compatibility and transporter-mediated uptake in cellular environments.

Overall, (3S,4R)-4-aminooxan-3-ol hydrochloride is a strategically important building block in the design and synthesis of chiral pharmaceuticals. Its defined stereochemistry, functional group diversity, and salt form enhance its utility in medicinal chemistry and drug development pipelines.