2-(3aR,4S,6R,6aS)-6-Aminotetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yloxyacetic acid RC00251

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:   www.cnroyalchem.com

【 Providing a complete set of intermediates and impurities for Ticagrelor 】

【 Providing a complete set of intermediates and impurities for Ticagrelor 】

【 Providing a complete set of intermediates and impurities for Ticagrelor 】

Below is a detailed product description for   2-((3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)oxyacetic acid  (CAS#  1402150-27-9 ):

Product Name

2-((3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)oxyacetic acid

CAS Number

1402150-27-9

Chemical Structure

Core Framework : Protected aminocyclopentane fused to a 1,3-dioxolane ring (ketal-protected  cis -fused bicyclic system).

Functional Groups :

Primary amino group (−NH₂) at position 6.

Carboxylic acid (−COOH) linked via an ether bridge (oxyacetic acid) at position 4.

Geminal dimethyl groups on the dioxolane ring (acetonide protecting group).

Stereochemistry : Specified enantiomer (3aR,4S,6R,6aS), indicating a defined chiral configuration.

Molecular Formula

C₁₁H₁₈NO₅

Molecular Weight

236.27 g/mol 

Purity

Typically ≥95% (HPLC), with enantiomeric excess (e.e.) >98% (chiral HPLC).

Physical Properties

Appearance : White to off-white crystalline solid or powder.

Solubility : Soluble in polar solvents (e.g., DMSO, methanol, water at acidic/basic pH); limited solubility in non-polar solvents.

Storage : −20°C under inert atmosphere (nitrogen/argon); desiccated to protect from moisture.

Key Features

Chirality : Single enantiomer with rigid stereochemistry, critical for biological activity.

Protecting Groups :

Acetonide (dioxolane) protects diol functionality.
− Primary amine (−NH₂) is unprotected/reactive.

Bifunctional Design :

Amino group: Enables nucleophilic reactions (e.g., amide coupling).

Carboxylic acid: Facilitates conjugation or salt formation.

Applications

Nucleic Acid Chemistry : Key synthon in  antisense oligonucleotide (ASO)  synthesis, particularly for:

Sugar-Modified Nucleotides : Serves as a conformationally constrained ribose/pentose analog.

Backbone Engineering : Used to introduce carbamate or amide linkages via amine-carboxylic acid coupling.

Prodrug Development : Intermediate for prodrugs targeting enzyme-responsive release.

Peptide Mimetics : Scaffold for designing peptidomimetics due to rigid cyclopentane core.

Synthesis

Prepared from protected ribose derivatives via:

Cyclization to form the cyclopenta[d][1,3]dioxolane core.

Stereoselective introduction of the amino group. 

Alkylation with haloacetate to install the carboxylic acid arm.

Handling & Safety

Stability : Sensitive to acid/base hydrolysis (cleaves acetonide); avoid prolonged exposure to air/moisture.

Hazards : Potential irritant (skin/eyes/respiratory). Use PPE (gloves, goggles) in a fume hood.

MSDS : Refer to material-specific safety data sheet for detailed handling protocols.