2-[[(3aR,4S,6R,6aS)-6-[7-Chloro-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol

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 】

H ere is a detailed product description for the compound with CAS RN 376608-75-2 and the chemical name   2-[[(3aR,4S,6R,6aS)-6-[7-Chloro-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol :

Product Name: 2-[[(3aR,4S,6R,6aS)-6-[7-Chloro-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]oxy]-ethanol  CAS Registry Number:  376608-75-2  Synonyms:  (Often derived from structure) * (1S,2R,3S,4R)-4-[2-Hydroxyethoxy]-2,3-O-(isopropylidene)-2,3-dihydroxycyclopentyl 7-chloro-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine  (Alternative naming based on cyclopentane numbering)  * [3aR-(3aα,4α,6β,6aα)]-Tetrahydro-6-[7-chloro-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl 2-Hydroxyethyl Ether  (Older style)  * (Often abbreviated based on core structures, e.g., CPG Nucleoside Analog Intermediate)

Molecular Formula:  C₁₉H₂₆ClN₅O₄S  Molecular Weight:  455.96 g/mol

Chemical Structure

[Insert High-Resolution Chemical Structure Diagram Here]  (Key structural features:)

Core Heterocycle:  7-Chloro-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidine. This is a fused tricyclic system resembling modified purines (like adenine/guanine analogs), acting as a nucleobase mimic.

Carbohydrate Moiety:  Tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxol (a protected cyclopentane diol). This is a  cyclopentyl sugar analog , mimicking the ribose ring found in natural nucleosides.

Glycosidic Linkage:  The triazolopyrimidine core is attached at the N3 position to the C1' position (anomeric carbon) of the cyclopentane ring via a C-N bond.  Crucially, the stereochemistry is defined as (3aR,4S,6R,6aS).

Functional Group:  A 2-hydroxyethoxy group attached via an ether linkage to the C4' position of the cyclopentane ring (O-CH₂-CH₂-OH).

Protecting Group:  The 2,2-dimethyl group indicates an  acetonide protecting group  on the C2' and C3' hydroxyls of the cyclopentane diol.

Stereochemistry:  Absolutely defined as  (3aR,4S,6R,6aS) . This specifies the relative and absolute configuration at all chiral centers within the cyclopentane ring system and the linkage. This stereochemistry is critical for biological activity if it targets nucleoside-binding sites.

Solubility

Solubility is highly dependent on the specific polymorph and solvent system. Generally:

Moderately soluble in polar aprotic solvents (DMSO, DMF, acetonitrile).

Sparingly soluble to soluble in chlorinated solvents (DCM, chloroform).

Limited solubility in water and lower alcohols (MeOH, EtOH). May require heating or sonication.

Low solubility in non-polar solvents (hexane, ether).

Storage Conditions

Store at -20°C or below.

Store under inert atmosphere (Argon or Nitrogen) when possible to prevent oxidation or moisture uptake.

Store in a tightly sealed, light-resistant container.

Allow vial to reach ambient temperature before opening to prevent condensation.

Handling Precautions

Handle in a well-ventilated fume hood.

Wear appropriate personal protective equipment (PPE): lab coat, safety glasses, nitrile gloves.

Avoid contact with skin, eyes, and clothing. Avoid inhalation of dust or aerosols.

Avoid generating dust. Use grounding procedures if handling large quantities. 

Wash hands thoroughly after handling.

Intended Use

Research Use Only (RUO). Not for diagnostic or therapeutic use in humans or animals.

Primarily used as a  key intermediate  or  building block  in the synthesis of more complex molecules, especially novel  nucleoside analogs  or  modified nucleosides/nucleotides .

Potential interest in medicinal chemistry research targeting:

Purinergic Receptors (P2Y receptors):  The triazolopyrimidine core is a known scaffold for antagonists (e.g., related to Ticagrelor/Cangrelor analogs targeting P2Y₁₂ for antiplatelet therapy).

Kinases:  ATP-competitive inhibitors.

Other Nucleoside-Binding Proteins.

The defined stereochemistry makes it valuable for structure-activity relationship (SAR) studies.

The acetonide protects the diol, allowing selective manipulation of the terminal hydroxyethoxy group.

Safety Information (Potential Hazards - Based on Structural Alerts)

Harmful if swallowed (H302).

Harmful in contact with skin (H312).

Causes serious eye irritation (H319).

May cause respiratory irritation (H335).  (Dust hazard).

Specific Target Organ Toxicity (Single Exposure):  Organ damage possible (H371). (General warning based on pharmacological activity potential).

Contains Nitrogen/Sulfur/Chlorine - thermal decomposition may release toxic fumes (NOx, SOx, HCl).

Not a complete safety assessment.  A full Safety Data Sheet (SDS) must be consulted prior to handling.