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

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 the compound   1858267-99-8 (2-(((3aR,4S,6R,6aS)-6-(7-amino-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol) :

1. Chemical Identification

CAS Number:  1858267-99-8 

Systematic Name:  2-(((3aR,4S,6R,6aS)-6-(7-Amino-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol

Synonyms:

(3aR,4S,6R,6aS)-6-[7-Amino-5-(propylsulfanyl)-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-4-(2-hydroxyethoxy)-2,2-dimethyl-3a,4,6,6a-tetrahydrocyclopenta[d][1,3]dioxole

2-({(3aR,4S,6R,6aS)-6-[7-Amino-5-(propylsulfanyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl]-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}oxy)ethanol

Protected Nucleoside Analog Intermediate (descriptive, not official)

Molecular Formula:  C₂₁H₃₁N₇O₄S

Molecular Weight:  477.58 g/mol

2. Structural Features

Core Nucleobase Analog:  Contains a  7-amino-5-(propylthio)-3H-[1,2,3]triazolo[4,5-d]pyrimidine  moiety. This is a bicyclic heterocycle resembling a modified purine:

[1,2,3]Triazolo[4,5-d]pyrimidine  core fused from triazole and pyrimidine rings.

7-Amino (-NH₂):  Key substituent essential for mimicking adenine/guanine interactions.

5-(Propylthio) (-S-CH₂-CH₂-CH₃):  Sulfur-containing alkyl chain substituent, influencing lipophilicity and potentially target binding.

Protected Sugar Moiety:  Features a  2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl  group attached to the nucleobase via a C-N bond at the triazole N3 position.

This is a  cyclopentyl ring fused to a 1,3-dioxolane acetal  protecting group ( O-CH(CH₃)-O  bridge).

The  2,2-dimethyl  groups provide steric protection to the acetal.

Specific Stereochemistry:  Defined chiral centers at positions 3aR, 4S, 6R, 6aS. This absolute configuration is crucial for biological activity, mimicking the D-ribose configuration in natural nucleosides.

Ethylene Glycol Linker:  Connected to the 4-position of the protected sugar via an ether linkage is a  2-hydroxyethoxy  group ( -O-CH₂-CH₂-OH ). This hydrophilic linker extends the molecule and provides an additional site for potential modification or interaction. 

3. Physical Properties (Typical)

Appearance:  White to off-white solid (powder, crystals, or amorphous).

Solubility:  Moderately soluble in polar organic solvents (e.g., DMSO, DMF, methanol, acetonitrile). Low solubility in water and non-polar solvents (e.g., hexane).

Melting Point:  Specific value requires experimental determination (literature/data sheet), expected >100°C.

Storage:  Store at  -20°C or below , protected from light and moisture (desiccated). Under inert atmosphere (Ar/N₂) for long-term storage. Highly sensitive to acid (hydrolysis of acetal) and potentially oxidation (thioether).

4. Chemical Properties

Reactivity:  The  acetal protecting group  is sensitive to acidic conditions (hydrolyzes to ketone/diol). The  primary alcohol  (-CH₂OH) terminus can undergo standard alcohol reactions (e.g., esterification, etherification, oxidation). The  thioether  (-S-Propyl) is susceptible to oxidation (to sulfoxide/sulfone). The  7-amino group  can act as a nucleophile or participate in hydrogen bonding.

Chirality:  Exists as a single defined stereoisomer (3aR,4S,6R,6aS). Enantiomeric purity is critical (>98% ee typical for research use).

5. Purpose & Applications

Primary Use:   Advanced Synthetic Intermediate  in medicinal chemistry research.

Target Class:   Nucleoside/Nucleotide Analog  development.

Potential Therapeutic Areas:

Antiviral Agents (e.g., targeting viral polymerases like HCV NS5B, Coronaviruses, Flaviviruses).

Anticancer Agents (e.g., targeting DNA/RNA synthesis, kinases).

Potential applications in treating parasitic diseases.

Role:  The structure combines a biologically active modified nucleobase (7-amino-triazolopyrimidine with lipophilic thioether) with a protected cyclopentyl-carbasugar core (mimicking ribose) and a flexible hydroxyethyl linker. This design aims to:

Enhance metabolic stability (acetal protection, carbasugar).

Modulate lipophilicity/solubility (thioether vs. hydroxyethyl linker).

Improve target binding affinity or selectivity.

Serve as a precursor for prodrugs (e.g., phosphates, amino acid esters targeting the alcohol).

6. Handling & Safety

Handling:  Use in a well-ventilated fume hood. Wear appropriate PPE: lab coat, safety glasses, nitrile gloves. Avoid contact with skin, eyes, and inhalation of dust. Avoid exposure to acids.

Stability:  Stable under inert conditions at low temperatures. Degrades upon exposure to moisture, strong acids/bases, oxidizing agents, and prolonged light. Solutions in DMSO should be aliquoted and stored frozen; avoid repeated freeze-thaw cycles.

Safety Data:   No specific toxicity data readily available.  Treat as potentially hazardous. Assume toxicity and handle with caution. Refer to a Safety Data Sheet (SDS) for specific hazard information if available from the supplier. Dispose of according to institutional regulations for hazardous organic compounds.