(2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran

 (2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran

(2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran (CAS No. 74801-29-9) is a complex organic compound notable for its applications in synthetic organic chemistry and carbohydrate chemistry. This compound features multiple functional groups that enhance its reactivity and utility in various chemical reactions.

Chemical and Physical Properties

• CAS Number: 74801-29-9
• MDL Number: MFCD06657856
• EINECS: Not specified
• Molecular Formula: C₄₀H₄₀O₅S
• Molecular Weight: 632.81 g/mol
• Boiling Point: 738.5 ± 60.0 °C
• Melting Point: 89 °C
• Flash Point: 400.44 °C
• Density: 1.22 ± 0.1 g/cm³
• Appearance: Typically appears as a white to off-white powder

Structure and Composition

The structure of this compound includes a tetrahydropyran ring with three benzyloxy groups and a phenylthio group. The presence of these substituents contributes to its solubility and reactivity, making it a valuable intermediate in various synthetic pathways.

Biological Activity and Applications

1. Synthetic Intermediate: This compound serves as an important intermediate in the synthesis of glycosides and other carbohydrate derivatives, facilitating the study of carbohydrate chemistry.
2. Research Applications: It is utilized in biochemical research for the synthesis of complex carbohydrates and in studies related to enzyme interactions.
3. Potential Pharmaceutical Uses: Due to its structural characteristics, it may have potential applications in drug development, particularly in the design of glycosylated compounds.

Synthesis Methods

The synthesis of (2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran typically involves multi-step synthetic routes that include protection-deprotection strategies for hydroxyl groups and the introduction of the phenylthio group through thiolation reactions.

Safety and Handling

While generally considered safe when handled properly, standard laboratory safety protocols should be followed to prevent exposure to skin or eyes.

Storage Recommendations

For long-term stability, store the compound at temperatures between 2–8°C in a cool, dry place away from light.

In summary, (2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran is an important compound in organic synthesis with applications in carbohydrate chemistry and potential pharmaceutical development.

Citations:

1. https://www.lookchem.com/cas_74801-29-9_suppliers.html
2. https://www.chemicalbook.com/ChemicalProductProperty_US_CB41232099.aspx
3. https://www.chemicalbook.in/product/phenyl2346-tetra-o-benzyl-b-d-thiogalactopyranoside-41232099
4. https://localpharmaguide.com/chemicalDetails.php?id=368272
5. https://www.chemimpex.com/fr/products/32228
6. https://www.medchemexpress.com/gal-2346bn-%CE%B2-sph.html
7. https://jiuzhoua.lookchem.com/products/CasNo-74801-29-9-Phenyl2-3-4-6-tetra-O-benzyl-b-D-thiogalactopyranoside-29890787.html
8. https://www.spectrumchemical.com/MSDS/TCI-P1679.pdf