(2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

(2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

(2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (CAS No. 24404-53-3) is a complex organic compound that plays a significant role in carbohydrate chemistry and synthetic organic chemistry. This compound is particularly useful in the synthesis of glycosides and other carbohydrate derivatives due to its unique structural features.

Chemical Properties

• CAS Number: 24404-53-3
• MDL Number: MFCD06657849
• EINECS: Not available
• Molecular Formula: C20H24O9S
• Molecular Weight: 440.46 g/mol
• Boiling Point: 514.6 °C (predicted)
• Melting Point: 68-72 °C
• Density: Approximately 1.313 g/cm³

Structure and Composition

The structure of (2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate consists of several key components:

1. Acetoxymethyl Group: The acetoxymethyl functional group at position 2 enhances the compound’s reactivity and solubility, making it suitable for various chemical reactions.
2. Phenylthio Group: The presence of the phenylthio group at position 6 provides a hydrophobic character that can influence the compound’s interaction with biological membranes and proteins.
3. Triacetate Structure: The triacetate groups at positions 3, 4, and 5 serve to protect hydroxyl groups, facilitating selective reactions during synthesis while enhancing stability.
4. Tetrahydropyran Ring: The tetrahydropyran ring structure is essential for maintaining the compound’s conformation and biological activity.

Applications

(2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate is utilized in several applications:

Biochemical Research

1. Glycoside Synthesis: This compound can be used as a precursor in the synthesis of various glycosides and oligosaccharides, which are important in biological systems.
2. Carbohydrate Chemistry: Its unique structure makes it valuable for studying carbohydrate interactions and modifications in biochemical pathways.

Pharmaceutical Development

1. Drug Design: The compound’s ability to interact with biological systems makes it a candidate for developing glycosylated drugs that require specific targeting mechanisms.

Chemical Synthesis

1. Intermediate in Organic Synthesis: It can serve as an intermediate in the synthesis of more complex organic molecules and pharmaceuticals.

Safety and Handling

While specific safety data for (2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate are not extensively documented, standard laboratory safety practices should be followed:

1. Personal Protective Equipment (PPE): Use gloves, goggles, and lab coats when handling this compound to avoid skin or eye contact.
2. Ventilation: Work in a well-ventilated area or fume hood to minimize exposure to vapors or dust.
3. Storage Conditions: Store the compound at -20 °C to maintain stability and prevent degradation.
4. Disposal Guidelines: Dispose of waste according to local regulations regarding hazardous materials.

Summary

In summary, (2R,3S,4S,5R,6S)-2-(Acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (CAS No. 24404-53-3) is an important reagent in carbohydrate chemistry for synthesizing glycosides and studying carbohydrate interactions. Its unique structural features enable its use in various applications within biochemical research and pharmaceutical development.

Citations:

1. https://www.capotchem.com/doc/viewmsds_24404-53-3.html
2. https://pubchem.ncbi.nlm.nih.gov/compound/10950254
3. https://www.evitachem.com/product/evt-343214
4. https://www.bldpharm.com/products/24404-53-3.html
5. https://www.lookchem.com/cas-244/24404-53-3.html
6. https://chemwill.lookchem.com/products/CasNo-24404-53-3-PHENYL-2-3-4-6-TETRA-O-ACETYL-1-THIO-BETA-D-GALACTOPYRANOSIDE-CAS-24404-53-3-In-stock-23325705.html
7. https://bak.chemsrc.com/en/cas/24404-53-3_684601.html
8. https://www.vulcanchem.com/product/vc3736719