β-D-Glucopyranosyl Azide 2,3,4,6-Tetraacetate

β-D-Glucopyranosyl Azide 2,3,4,6-Tetraacetate

β-D-Glucopyranosyl Azide 2,3,4,6-Tetraacetate is a chemical compound used primarily in biochemical research and synthetic chemistry. It serves as a versatile intermediate for various applications, including the synthesis of glycosylated compounds and protein conjugates.

Chemical Properties

• CAS Number: 13992-25-1
• MDL No.: MFCD00216966
• Catalog Number: A807599
• EINECS: Not available
• Molecular Formula: C₁₄H₁₉N₃O₉
• Molecular Weight: 373.32 g/mol
• Boiling Point: 502.57 °C
• Melting Point: 127–131 °C
• Density: 1.3271 g/cm³
• Appearance: Not available (typically described as a crystalline solid)
• Storage Conditions: Store at 2–8 °C for long-term stability (months).
• Optical Rotation: Not specified
• Refractivity: Estimated at 1.5700

Applications

1. Synthetic Chemistry:
   • Used as an azide donor in click chemistry reactions, facilitating the synthesis of glycosylated compounds and other bioconjugates.
   • Acts as an intermediate in the preparation of various coupled conjugates of D-glucose.
2. Biochemical Research:
   • Employed in studies involving protein tyrosine phosphatase inhibition, contributing to the understanding of enzyme mechanisms and signaling pathways.
   • Useful in the development of glycomimetics and carbohydrate-based pharmaceuticals.
3. Glycobiology:
   • Important for studying carbohydrate interactions and modifications in biological systems, aiding in the exploration of glycan functions.

Safety Profile

While specific safety data for β-D-glucopyranosyl azide is limited, standard laboratory safety protocols should be followed when handling this compound. Use appropriate personal protective equipment (PPE) to minimize exposure.

Conclusion

β-D-Glucopyranosyl Azide 2,3,4,6-Tetraacetate (CAS No. 13992-25-1) is a valuable compound in synthetic and biochemical research. Its ability to participate in click chemistry and its role as an azide donor make it essential for the development of glycosylated compounds and bioconjugates.

References

1. PubChem – 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl azide1
2. ChemicalBook – 1-Azido-2,3,4,6-tetra-O-acetyl-beta-D-glucose2
3. Glyco MindSynth – β-D-Glucopyranosyl azide4
4. Synthose – 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl azide5

This detailed description includes accurate chemical properties and applications based on the provided search results. If you need further adjustments or additional information, please let me know!

Citations:

1. https://pubchem.ncbi.nlm.nih.gov/compound/2_3_4_6-Tetra-O-acetyl-beta-D-glucopyranosyl-azide
2. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0264387.htm
3. https://pubchem.ncbi.nlm.nih.gov/compound/4114495
4. https://glycomindsynth.com/product_detail/717/Monosaccharide
5. https://synthose.com/products/TG948
6. https://www.biosynth.com/p/MT01035/13992-25-1-2346-tetra-o-acetyl-v-d-glucopyranosy
7. https://www.alfa-chemistry.com/cas_13992-25-1.htm
8. https://synthose.com/products/TL257