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

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

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-D-galactopyranose (CAS: 155417-78-0) is a specialized carbohydrate derivative notable for its use in synthetic organic and medicinal chemistry, primarily as an intermediate in drug development and carbohydrate chemistry research.synthose+2

Chemical Properties

• Molecular Formula: C₁₄H₁₉N₃O₉glentham+1

• Molecular Weight: 373.32 g/molsynthose+1

• Appearance: White crystalline solidsynthose

• Melting Point: 118–120 °Csynthose

• Purity: Minimum 98% (typically by ¹H-NMR)synthose

• Solubility: Freely soluble in DMF, DMSO, MeOH, DCM, EtOAcsynthose

Structural Information

• IUPAC Name: [(2R,3R,4S,5R)-3,5,6-Triacetyloxy-4-azidooxan-2-yl]methyl acetatesynthose

• SMILES: C(C)(=O)OC[C@H]1OC(C@@HOC(C)=O)OC(C)=Osynthose

• InChI: InChI=1S/C14H19N3O9/c1-6(18)22-5-10-12(23-7(2)19)11(16-17-15)13(24-8(3)20)14(26-10)25-9(4)21/h10-14H,5H2,1-4H3/t10-,11+,12+,13-,14?/m1/s1synthose

Synthesis and Application

• This compound is typically synthesized by azidation and acetylation of galactopyranose derivatives, with the azido group introduced at the 3-position and acetyl groups used to protect hydroxyls on positions 1, 2, 4, and 6.bocsci+1

• It is widely used as an intermediate in the synthesis of biologically relevant oligosaccharides and glycosylated drugs.americanchemicalsuppliers+1

• Its azido group provides a handle for further modifications via click chemistry or other types of functionalization.bocsci

Storage and Handling

• Storage: Store at 0 to -20 °C for optimal stability.synthose

• Shipping: Ships ambient, express recommended.synthose

• Safety: Not classified as hazardous under GHS standards.synthose

Regulatory Notes

• DSL Status (Canada): Not listedsynthose

• TSCA Certification (USA): Negative certificationsynthose

Synonyms

• 3-Azido-3-deoxy-D-galactopyranose 1,2,4,6-tetraacetate

• Tetra-O-acetyl-3-azido-3-deoxy-D-galactopyranosechemicalbook

This compound is a valuable synthetic building block in carbohydrate and pharmaceutical chemistry, particularly where azido sugar motifs are critical for further biochemical elaborations.americanchemicalsuppliers+2