N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester RC00233

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   N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester (CAS 274693-54-8) :

Product Identification

Chemical Name:
N-[(3aS,4R,6S,6aR)-Tetrahydro-6-(2-hydroxyethoxy)-2,2-dimethyl-4H-cyclopenta-1,3-dioxol-4-yl]carbamic acid phenylmethyl ester
Synonym: Benzyl N-[(3aS,4R,6S,6aR)-6-(2-hydroxyethoxy)-2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]dioxol-4-yl]carbamate

CAS Registry Number:  274693-54-8

Molecular Formula:  C₂₀H₂₇NO₇ 

Molecular Weight:  393.44 g/mol

Chemical Structure & Properties

Core Structure:  Features a  cyclopentane ring fused to a 1,3-dioxolane protecting group  (2,2-dimethyl-4H-cyclopenta-1,3-dioxol).

Chirality:  Contains four defined stereocenters: (3a S ,4 R ,6 S ,6a R ). This stereochemistry is crucial for its biological activity and reactivity.

Functional Groups:

Benzyl carbamate (Cbz protecting group):   -NHC(O)OCH₂C₆H₅  attached to the cyclopentane ring (position 4).

2-Hydroxyethoxy ether:   -OCH₂CH₂OH  attached to the dioxolane ring (position 6).

Acetonide protecting group:  The 2,2-dimethyl-1,3-dioxolane ring protects a diol functionality.

Solubility:  Soluble in polar organic solvents (e.g., dichloromethane, chloroform, DMSO, acetone, ethyl acetate). Limited solubility in water.

Stability:  Stable under inert conditions at low temperatures (-20°C).  Moisture-sensitive  and may decompose upon prolonged exposure to air, acids, or elevated temperatures. Susceptible to cleavage of the Cbz group under hydrogenolysis conditions.

Applications & Significance

Key Intermediate:  Primarily used as a  high-value synthetic intermediate  in organic chemistry, especially in the multi-step synthesis of complex bioactive molecules.

Target Molecules:  Plays a critical role in synthesizing modified  nucleoside analogs , particularly those with antiviral or anticancer activity. The stereochemistry and protecting groups (acetonide, Cbz) facilitate selective downstream modifications.

Protecting Group Strategy:

The  acetonide  protects a  cis -diol.

The  benzyl carbamate (Cbz)  protects an amine, removable via catalytic hydrogenation or dissolving metal reduction.

The  primary alcohol  ( -CH₂CH₂OH ) offers a handle for further derivatization (e.g., phosphorylation, esterification).

Handling & Storage

Storage:  Store at  -20°C or below  under inert atmosphere (Argon/Nitrogen) in a tightly sealed, light-resistant container.

Handling Precautions:

Use in a well-ventilated fume hood.

Wear appropriate PPE: nitrile gloves, safety goggles, lab coat.

Avoid contact with skin, eyes, and inhalation of dust.

Handle under anhydrous conditions using standard Schlenk techniques if necessary.

Stability Concerns:  Monitor for decomposition (discoloration, change in consistency). Avoid exposure to strong acids/bases, oxidizing agents, and moisture.

Safety Information (General Guidance)

Hazard Statements (Predicted):  H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation).

Precautionary Measures:  P261 (Avoid breathing dust/fume), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes), P302+P352 (IF ON SKIN: Wash with plenty of soap and water).

Safety Data Sheet (SDS):  Consult the specific SDS provided by the supplier prior to use.