2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol (2R,3R)-2,3-dihydroxybutanedioate
[CAS# 376608-65-0]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol (2R,3R)-2,3-dihydroxybutanedioate
• Molecular Formula: C₁₀H₁₉NO₄.C₄H₆O₆
• Molecular Weight: 367.35
• CAS Registry Number: 376608-65-0
• EC Number: 690-047-9
• SMILES: CC1(O[C@H]2[C@@H](C[C@@H]([C@H]2O1)OCCO)N)C.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

2-[[(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol (2R,3R)-2,3-dihydroxybutanedioate is a complex organic compound with applications in pharmaceutical and biochemical research. This substance consists of a fused cyclopentane-dioxolane core with an aminated functional group, an ethoxy linkage, and a dihydroxybutanedioate moiety, making it structurally significant for drug development and synthesis of biologically active molecules.

The discovery of this compound stems from the study of sugar-derived analogs and their potential as pharmaceutical agents. Research into structurally related molecules has focused on their roles in modifying biological activity, particularly in enzyme inhibition, receptor modulation, and drug delivery systems. The presence of an aminotetrahydrocyclopenta-dioxolane core is characteristic of compounds with notable pharmacological properties, and further studies have led to the synthesis of derivatives with enhanced stability and bioactivity.

Applications of this compound include its potential use as an intermediate in the synthesis of antiviral, antibacterial, and neuroactive agents. The combination of hydroxyl and amino functionalities allows for interactions with biomolecular targets, making it suitable for medicinal chemistry. Additionally, the dihydroxybutanedioate salt form improves solubility and bioavailability, essential factors in drug formulation.

Ongoing research explores the compound’s role in the development of enzyme inhibitors targeting metabolic pathways. Structural modifications have been studied to optimize its binding affinity to biological targets, contributing to advancements in rational drug design. Further investigations into its physicochemical properties and reactivity may expand its applications in pharmaceutical science and organic synthesis.

References

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