2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-delta-lactone

2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-delta-lactone 

2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-delta-lactone (CAS No. 32384-65-9) is a silylated derivative of D-gluconolactone, primarily used as an intermediate in the synthesis of sodium-glucose cotransporter inhibitors, such as dapagliflozin, which is utilized for managing type 2 diabetes.

Chemical and Physical Properties

• CAS Number: 32384-65-9
• MDL Number: MFCD22665922
• EINECS: Not specified
• Molecular Formula: C₁₈H₄₂O₆Si₄
• Molecular Weight: 466.86 g/mol
• Boiling Point: 417.2 ± 45.0°C at 760 mmHg
• Melting Point: Not specified
• Flash Point: 171°C
• Density: Not specified
• Appearance: Colorless liquid

Structure and Composition

This compound features a tetrahydro-pyran structure with four trimethylsilyl groups attached to the hydroxyl positions of the D-glucono moiety. The presence of these silyl groups enhances the compound’s stability and solubility in organic solvents.

Biological Activity and Applications

1. Intermediate in Drug Synthesis: 2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-delta-lactone is primarily used in the pharmaceutical industry as an intermediate for synthesizing SGLT2 inhibitors like dapagliflozin and canagliflozin, which are crucial for treating type 2 diabetes by promoting glucose excretion through urine.
2. Chemical Reagent: It serves as a reagent in various organic synthesis processes due to its ability to protect hydroxyl groups during reactions.

Synthesis Methods

The synthesis of this compound typically involves reacting D-gluconolactone with trimethylsilyl chloride or hexamethyldisilazane in the presence of an acid-binding agent or ionic liquids to enhance yield and reduce environmental impact.

Safety and Handling

While generally considered safe when handled properly, it is advisable to use personal protective equipment (PPE) when working with this compound to avoid skin and eye contact.

Storage Recommendations

For optimal stability, store 2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-delta-lactone at temperatures between 2–8°C in a cool, dry place away from light.

In summary, 2,3,4,6-Tetra-O-(trimethylsilyl)-D-glucono-delta-lactone is a valuable intermediate in pharmaceutical chemistry with significant applications in the synthesis of antidiabetic agents.

Citations:

1. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB32610563.htm
2. https://patents.google.com/patent/CN112341488B/en
3. https://www.tcichemicals.com/IN/en/p/T4205
4. https://www.bldpharm.com/products/32384-65-9.html
5. https://www.lgcstandards.com/FR/en/2-3-4-6-Tetrakis-O-trimethylsilyl-D-gluconolactone/p/TRC-T279540-5G
6. https://www.sigmaaldrich.com/AR/en/product/ambeedinc/ambh46a964ce?context=bbe
7. https://www.ambeed.com/products/32384-65-9.html
8. https://www.indiamart.com/proddetail/2-3-4-6-tetrakis-o-trimethylsilyl-d-gluconolactone-powder-2848978836497.html