1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranose

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranose (CAS No. 81704-02-1)

1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranose is a chemically modified galactose derivative with applications in organic synthesis and biochemical research. Below is a comprehensive overview:

Chemical Identity

• CAS Number: 81704-02-1
• Product Code: A1251209
• Molecular Formula: C₂₂H₂₃NO₁₁
• Molecular Weight: 477.4 g/mol
• IUPAC Name: 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-β-D-galactopyranose

Physical Properties

• Appearance: White crystalline solid
• Purity: ≥98% (confirmed by ¹H-NMR)
• Melting Point: Not explicitly listed, but structurally similar compounds show high thermal stability.
• Solubility: Soluble in DMSO and common organic solvents like dichloromethane.

Structural Features

This compound features:

• A β-D-galactopyranose backbone with acetyl groups at the 1, 3, 4, and 6 positions.
• A phthalimido group (-N-phthaloyl) replacing the hydroxyl group at the 2-position, enhancing stability and reactivity for further chemical modifications.
• Stereochemical configuration preserved in the β-anomeric form.

Applications

• Glycosylation Reactions: Used as a protected intermediate in carbohydrate synthesis.
• Pharmaceutical Research: Serves as a precursor for glycosidase inhibitors or glycomimetic drugs.
• Biochemical Probes: Employed in studies of enzyme-substrate interactions.

Safety and Handling

• Hazard Statements:
  • H302: Harmful if swallowed
  • H317: May cause allergic skin reaction.
• Precautionary Measures:
  • P280: Wear protective gloves/eye protection.
  • P305+P351+P338: Rinse eyes cautiously if exposed.
• Storage: Store at ambient temperature in a tightly sealed container, protected from moisture.

Regulatory and Compliance

• TSCA Status: Listed on the Toxic Substances Control Act inventory.
• DSL Status: Not included in Canada’s Domestic Substances List.

This compound is commercially available in quantities ranging from 1g to 25g, with applications in academic and industrial research.

Citations:

1. https://pubchem.ncbi.nlm.nih.gov/compound/1_3_4_6-Tetra-O-acetyl-2-deoxy-D-glucopyranose
2. https://pubchem.ncbi.nlm.nih.gov/compound/10504797
3. https://chempep.com/product/1346-tetra-o-acetyl-2-deoxy-2-phthalimido-d-galactopyranose/
4. https://synthose.com/products/AL363
5. https://www.sigmaaldrich.com/US/en/product/bldpharmatechcoltd/bl3h160c1ed6?context=bbe
6. https://www.tcichemicals.com/IN/en/p/T2047
7. https://www.sigmaaldrich.com/US/en/product/ambeedinc/ambh580649d9?context=bbe
8. https://www.tcichemicals.com/CA/en/p/T4028
9. https://www.sigmaaldrich.com/IN/en/product/achemblock/advh996bea28?context=bbe
10. https://www.sigmaaldrich.com/ES/en/product/aldrich/728314
11. https://synthose.com/products/AG327
12. https://www.tcichemicals.com/IE/en/p/T2047
13. https://www.biosynth.com/p/MA07056/3006-60-8-2-acetamido-1346-tetra-o-acetyl-2-deox
14. https://pubchem.ncbi.nlm.nih.gov/compound/1286737-83-4
15. https://pubchem.ncbi.nlm.nih.gov/compound/6547253
16. https://pubchem.ncbi.nlm.nih.gov/compound/133445