Benzyl ((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate RC00234

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   Benzyl ((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)carbamate  (CAS 274693-53-7):

1. Chemical Identification:

Systematic Name:  

Benzyl [(3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]carbamate

CAS Registry Number:  274693-53-7

Synonyms:

N-[(3aS,4R,6S,6aR)-6-Hydroxy-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]carbamic acid benzyl ester

Cbz-Protected Aminodiol Acetonide (specific stereoisomer)

(1R,2S,3S,4R)-4-[(Benzyloxycarbonyl)amino]-2,3-(isopropylidenedioxy)cyclopentanol

Molecular Formula:  C₁₈H₂₃NO₅

Molecular Weight:  333.38 g/mol

2. Structural Features:

Core Structure:  A fused bicyclic system consisting of a cyclopentane ring fused to a 1,3-dioxolane ring (a cyclic acetal).

Protecting Groups:

2,2-Dimethyl-1,3-dioxolane (Acetonide):  Protects a  cis -vicinal diol (on the cyclopentane ring) as a cyclic acetal. This is sensitive to acid hydrolysis.

Benzyloxycarbonyl (Cbz or Z):  A carbamate group protecting the primary amine (-NH₂) at position 4 of the cyclopentane ring as a benzyl carbamate (-NH-C(=O)O-CH₂-C₆H₅). This group is typically removed by catalytic hydrogenation or dissolving metal reduction.

Functional Groups:

Secondary Alcohol (-OH) at position 6 of the cyclopentane ring.

Protected Primary Amine (Cbz-NH-) at position 4 of the cyclopentane ring.

Stereochemistry:  Defined absolute configuration at four chiral centers: 3a S , 4 R , 6 S , 6a R . This specific enantiomer is crucial for its intended use as a synthon in chiral synthesis, particularly for carbocyclic nucleosides. The acetonide ring implies the protected diol has a  cis  relationship.

3. Physical Properties (Typical):

Appearance:  Typically a white to off-white crystalline solid or powder.

Melting Point:  Often reported in the range of 120-130 °C (specific batch-dependent).

Solubility:

Soluble in common organic solvents: Dichloromethane (DCM), Chloroform, Ethyl Acetate (EtOAc), Tetrahydrofuran (THF), Dimethylformamide (DMF), Dimethyl Sulfoxide (DMSO).

Low solubility in water and non-polar solvents like hexanes.

Optical Rotation:  [α]D²⁵ values are typically reported as significantly negative (e.g., -30° to -50°) in solvents like methanol or chloroform, confirming the specific enantiomer.

4. Chemical Properties:

Stability:

Stable under basic conditions and typical organic reaction conditions (e.g., nucleophilic substitutions with the alcohol).

Acid-Sensitive:  The acetonide protecting group is hydrolyzed by aqueous acid (e.g., dilute H₂SO₄, HCl, TFA, AcOH/H₂O) to reveal the  cis -diol.

Reduction/Hydrogenation Sensitive:  The Cbz group is cleaved by catalytic hydrogenation (H₂/Pd-C) or dissolving metals (e.g., Na/liquid NH₃) to reveal the free primary amine.

Reactivity:

The secondary alcohol (-OH) at C6 can undergo typical alcohol reactions: esterification, etherification, oxidation (carefully controlled), and nucleophilic substitution if activated (e.g., mesylation, tosylation).

The carbamate nitrogen is relatively unreactive due to protection, but the carbonyl can participate in reactions under specific conditions.

The benzene ring can undergo electrophilic aromatic substitution under forcing conditions, although this is rarely desirable.

5. Primary Application & Significance:

Key Chiral Synthon / Building Block:  This compound is a highly valuable advanced intermediate in organic synthesis, specifically for the production of  carbocyclic nucleoside analogs .

Target Molecules:  It is a critical precursor in the enantioselective synthesis of pharmacologically important drugs, most notably:

Abacavir Succinate:  A potent nucleoside reverse transcriptase inhibitor (NRTI) used in the treatment of HIV infection. The specific (1R,2S,3S,4R) stereochemistry of this synthon mirrors the stereochemistry required in the cyclopentane ring of Abacavir after deprotection and further functionalization.

Other carbocyclic nucleoside analogs with antiviral or anticancer activity.

Role in Synthesis:  The molecule provides the correctly configured cyclopentane backbone with protected amine and diol functionalities. The synthesis typically involves:

Functionalization/modification of the C6 alcohol.

Selective deprotection of either the acetonide (acid) or the Cbz group (hydrogenation) at specific stages.

Construction of the nucleobase (e.g., purine, pyrimidine) onto the amine group after its deprotection.

6. Handling and Storage:

Storage:  Store in a cool (2-8°C recommended), dry place, protected from light and moisture. Under inert atmosphere (Argon/Nitrogen) for long-term stability.

Handling:  Handle in a well-ventilated fume hood. Use appropriate personal protective equipment (PPE): lab coat, safety glasses, nitrile gloves. Avoid contact with skin, eyes, and clothing. Avoid inhalation of dust.

Stability Considerations:  Sensitive to prolonged exposure to moisture (can slowly hydrolyze acetonide), strong acids (rapidly hydrolyzes acetonide), and strong reducing agents (cleaves Cbz). Keep containers tightly sealed.

7. Safety:

Refer to SDS:  Always consult the Safety Data Sheet (SDS) for the specific batch before handling. Hazards can vary.

Potential Hazards (Typical):  May cause skin and eye irritation. May be harmful if swallowed or inhaled (dust). Not typically classified as highly toxic or acutely hazardous, but treat with caution.

First Aid:  Flush eyes/skin with water if contacted. If inhaled, move to fresh air. If swallowed, rinse mouth and seek medical advice.