3-((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-5-(propylthio)-3H-[1,2,3] triazolo[4,5-d]pyrimidin-7-ol

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 】

Here is a detailed product description for CAS 1456538-51-4 , 3-((3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-5-(propylthio)-3H-[1,2,3] triazolo[4,5-d]pyrimidin-7-ol :

1. Chemical Identity  *  Chemical Name:  3-((3aS,4R,6S,6aR)-6-(2-Hydroxyethoxy)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl)-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol *  CAS Registry Number:  1456538-51-4 *  Synonyms:  (Common research codes might exist, but none are widely established based on the CAS alone). *  Molecular Formula:  C₁₈H₂₅N₅O₄S *  Molecular Weight:  407.49 g/mol (Calculated)

2. Structural Characteristics  *  Core Heterocycle:  The compound features a fused  3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ol  ring system. This core combines a triazole ring fused to a pyrimidine ring bearing a hydroxyl group at position 7. *  Key Substituents:  *  C5 (Pyrimidine):  A  propylthio group  (-S-CH₂-CH₂-CH₃) attached to position 5 of the triazolopyrimidine core. This alkylthioether linkage contributes to lipophilicity and potential bioisosterism. *  N3 (Triazole):  A complex  cyclopentyl-dioxolane sugar mimic  attached via N3 of the triazole ring. This substituent is specifically characterized as: *  (3aS,4R,6S,6aR)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl:  This signifies a bicyclic system where a cyclopentane ring is fused to a 1,3-dioxolane ring. * The stereochemistry (3aS,4R,6S,6aR) defines the three-dimensional arrangement of the chiral centers within this bicyclic structure. Absolute stereochemistry is specified. * The dioxolane ring (O-C(CH₃)₂-O) is a common  protecting group  for cis-diols, strongly suggesting this moiety is derived from a protected pentofuranose sugar (like ribose). *  O6 Modification:  A  2-hydroxyethoxy group  (-O-CH₂-CH₂-OH) is attached to the oxygen at position 6 of the sugar mimic. This hydrophilic chain extends from the dioxolane ring system.

3. Physicochemical Properties (Theoretical/Predicted)  *  Physical State:  Likely a solid at room temperature (common for compounds of this complexity and MW). *  Solubility:  Expected to have limited solubility in water due to the lipophilic triazolopyrimidine core, propylthio group, and dioxolane-protected sugar. Solubility may be moderate in polar organic solvents (DMSO, DMF, methanol, ethanol) and potentially enhanced in aqueous solutions containing co-solvents or surfactants due to the polar hydroxyl groups. *  Lipophilicity:  Moderate to high logP value predicted due to the heterocyclic core and alkyl chains (methyls on dioxolane, propylthio), partially countered by the hydroxyethoxy tail and the triazolopyrimidine hydroxyl. *  Stability:  Stability data specific to this compound is likely proprietary. General considerations: * The dioxolane protecting group is generally stable to bases but can be hydrolyzed under acidic conditions to reveal the diol. * The thioether linkage may be susceptible to oxidation. * The compound should be protected from light and moisture and stored at low temperatures for long-term stability.

4. Functional Significance  *  Nucleoside Analog:  The structure strongly indicates this compound is a synthetic  nucleoside analog . The triazolopyrimidine core mimics a purine base (like adenine or guanine), while the (3aS,4R,6S,6aR)-substituent mimics the β-D-ribofuranose sugar conformation found in natural nucleosides (protected as a dioxolane). *  Prodrug Potential:  The dioxolane group suggests it might be a  prodrug  form designed for improved stability, absorption, or targeted delivery. Enzymatic or acidic hydrolysis  in vivo  could potentially remove the dioxolane to generate the active nucleoside with free diol. *  Structural Modifications:  The C5 propylthio substitution and the O6' hydroxyethoxy modification are key distinguishing features designed to modulate: *  Target Binding:  Potency and selectivity towards specific enzymes (e.g., kinases, polymerases, nucleoside metabolizing enzymes). *  Pharmacokinetics:  Absorption, distribution, metabolism, excretion (ADME). *  Solubility:  The hydroxyethoxy tail specifically aims to increase polarity and aqueous solubility compared to standard protected nucleosides.

5. Potential Applications & Research Context  *  Research Compound:  Primarily of interest as a  specialized research chemical . *  Medicinal Chemistry:  Developed as a potential  pharmaceutical candidate  or intermediate in drug discovery programs. *  Therapeutic Target Areas:  Based on the nucleoside analog structure and modifications, potential therapeutic areas could include: *  Antiviral Agents:  Targeting viral polymerases/reverse transcriptases (e.g., for HCV, HBV, HIV, or other viruses). *  Anticancer Agents:  Targeting DNA/RNA synthesis, cell signaling kinases, or nucleoside metabolism pathways. *  Immunomodulators:  Targeting purine metabolism enzymes (e.g., PNP inhibitors). *  (Note: Specific biological activity must be confirmed experimentally; this is speculative based on structure class).

6. Handling and Safety  *  Classification:  Handling should assume it is a  potentially hazardous substance . *  Precautions:  Standard laboratory safety practices are essential: * Use personal protective equipment (PPE): lab coat, gloves, safety glasses. * Avoid inhalation of dust/aerosols and contact with skin/eyes. Work in a fume hood. * Handle with care considering potential biological activity. *  Storage:  Store under inert atmosphere (N₂ or Argon), protected from light, at freezer temperatures (-20°C or lower), desiccated. Specific stability data should be consulted if available. *  Safety Data:  A Safety Data Sheet (SDS) specifically for this CAS should be consulted before handling.