2-((3aR,4S,6R,6aS)-6-amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-tataric acid RC00232

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  376608-65-0   2-((3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol L-Tartaric Acid :

1. Chemical Identification:  *  CAS Registry Number:  376608-65-0 *  IUPAC Name:  2-((3aR,4S,6R,6aS)-6-Amino-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yloxy)ethanol (2R,3R)-2,3-dihydroxybutanedioate (1:1) *  Synonyms:  * 2-[(3aR,4S,6R,6aS)-6-Amino-2,2-dimethyl-3a,4,6,6a-tetrahydrocyclopenta[d][1,3]dioxol-4-yl]oxy]ethanol (2R,3R)-2,3-dihydroxysuccinate * (1R,2S,3R,4S)-4-(2-Hydroxyethoxy)-3-[(1-methylethylidene)amino]cyclopentane-1,2-diol (2R,3R)-2,3-dihydroxybutanedioate (less specific) * L-Tartrate salt of the amino alcohol derivative. *  Molecular Formula:   C₁₁H₂₁NO₅ • C₄H₆O₆  (or  C₁₅H₂₇NO₁₁  for the combined salt) *  Molecular Weight:  421.38 g/mol (for the combined salt C₁₅H₂₇NO₁₁)

2. Structural Characteristics:  *  Core Structure:  The compound features a  cyclopenta[d][1,3]dioxole  ring system. This is a bicyclic structure where a cyclopentane ring is fused to a 1,3-dioxolane ring (a 5-membered ring containing two oxygen atoms). *  Protecting Group:  The dioxolane ring incorporates a  2,2-dimethyl  group, forming an  acetonide  protecting group. This protects two vicinal diol groups present in the parent cyclopentane structure. *  Functional Groups:  *  Primary Amino Group (-NH₂):  Attached to the cyclopentane ring ( 6-amino ). *  Ether Linkage (-O-):  Connects the cyclopentane ring to an ethoxy chain. *  Hydroxyethoxy Chain (-O-CH₂-CH₂-OH):  A short polyethylene glycol (PEG)-like linker terminated with a primary alcohol. *  Salt Form:  The compound is supplied as the  L-Tartaric Acid salt  (specifically the (2R,3R)-enantiomer). This means the basic primary amine is protonated and associated with the mono-anion of L-tartaric acid [(2R,3R)-2,3-dihydroxysuccinic acid] in a 1:1 molar ratio. *  Stereochemistry:  The stereochemistry is explicitly defined as  (3aR,4S,6R,6aS) . This indicates an absolute configuration at each chiral center within the fused bicyclic system. The L-tartrate counterion also has defined (2R,3R) stereochemistry.  This specific stereochemistry is crucial for its intended applications.

3. Physical Properties:  *  Appearance:  Typically supplied as a  white to off-white crystalline powder  or solid. *  Solubility:  Expected to be soluble in polar solvents like water, methanol, ethanol, and dimethyl sulfoxide (DMSO), largely due to the ionic nature of the salt and the polar functional groups (amine, alcohols). Solubility in less polar solvents (e.g., ethyl acetate, dichloromethane) is likely low. *  Melting Point:  Specific melting point data is compound-dependent but generally falls within a range characteristic of organic salts (e.g., 100-200°C, decomposition may occur).  Requires specific batch data.  *  Optical Rotation:  Exhibits optical activity due to the multiple chiral centers. The specific rotation  [α]D  depends on concentration, solvent, and temperature.  Requires specific measurement.  *  Hygroscopicity:  May be slightly hygroscopic due to the ionic nature and presence of alcohol groups. Storage under dry conditions is recommended.

4. Chemical Properties:  *  Reactivity:  The primary amine group is nucleophilic and can participate in reactions like acylation, alkylation, reductive amination, and formation of carbamates or ureas. The primary alcohol group can undergo typical alcohol reactions (e.g., esterification, etherification, oxidation, tosylation). The acetonide protecting group is stable to base and mild acid but can be cleaved under aqueous acidic conditions to reveal the protected diol. *  Stability:  Stable under normal storage conditions (room temperature or below, dry, inert atmosphere). Sensitive to strong acids (cleaves acetonide), strong oxidizing agents, and potentially strong bases. Light sensitivity may be low, but storage in the dark is often recommended as a precaution. *  pKa:  The conjugate acid of the amine (ammonium ion) has a pKa typically around 8-10. The tartrate carboxylates have pKa values around ~3.0 and ~4.3.

5. Applications and Use:  *  Primary Use:  This compound is primarily a  specialized synthetic building block  or  intermediate  in organic and medicinal chemistry research. *  Target Synthesis:  Its structure suggests it is designed for synthesizing  modified nucleosides, nucleotides, or carbocyclic nucleoside analogs , particularly those targeting antiviral or anticancer activities. The protected diol and amino group mimic key features of ribose and nucleobases found in natural nucleosides. The hydroxyethoxy chain provides a handle for further modification or conjugation. *  Chiral Pool:  The defined stereochemistry makes it a valuable chiral starting material for enantioselective synthesis. *  Research Areas:  Primarily used in academic and industrial research laboratories focused on: * Medicinal Chemistry (Antiviral, Anticancer drug discovery) * Nucleoside Chemistry * Carbohydrate Chemistry * Prodrug Development * Bioconjugation (using the alcohol group)

6. Handling and Storage:  *  Storage Conditions:  Store at  2-8°C (refrigerated)  or preferably  -20°C  under an inert atmosphere (e.g., nitrogen or argon) in a tightly sealed container. Protect from moisture and light. Allow to warm to room temperature before opening to minimize moisture condensation. *  Handling:  Handle in a well-ventilated laboratory using standard personal protective equipment (PPE): lab coat, safety glasses, and suitable gloves (e.g., nitrile). Avoid inhalation of dust and contact with skin, eyes, or clothing. *  Stability under Storage:  When stored as recommended, the compound is typically stable for several years.

7. Safety Information:  *  Hazard Classification:  A full safety assessment requires specific toxicological data. As a general precaution with research chemicals: *  Hazard Statements (Likely):  H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). May also carry H302 (Harmful if swallowed), H317 (May cause an allergic skin reaction). *  Precautionary Statements:  P261 (Avoid breathing dust/fume/gas/mist/vapours/spray), P264 (Wash hands thoroughly after handling), P271 (Use only outdoors or in a well-ventilated area), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P302+P352 (IF ON SKIN: Wash with plenty of soap and water), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing). *  First Aid Measures:  Skin contact: Wash thoroughly with soap and water. Eye contact: Flush immediately with plenty of water for at least 15 minutes; seek medical attention. Inhalation: Move to fresh air; seek medical attention if respiratory irritation occurs. Ingestion: Rinse mouth; do NOT induce vomiting; seek medical attention immediately. *  Disposal:  Dispose of in accordance with local, regional, national, and international regulations. Consult a licensed waste disposal contractor. Do not dispose of down the drain.