[(2R,3R,4R,5R)-3,4,6-tris(acetyloxy)-5-azidooxan-2-yl]methyl acetate

• ChemBase ID: 161002
• Molecular Formular: C14H19N3O9
• Molecular Mass: 373.31536
• Monoisotopic Mass: 373.1121292
• SMILES: C1(O[C@H]([C@@H]([C@@H]([C@@H]1N=[N+]=[N-])OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C
• Canonical SMILES: [N-]=[N+]=N[C@@H]1C(OC(=O)C)O[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)COC(=O)C
• InChI: InChI=1S/C14H19N3O9/c1-6(18)22-5-10-12(23-7(2)19)13(24-8(3)20)11(16-17-15)14(26-10)25-9(4)21/h10-14H,5H2,1-4H3/t10-,11-,12+,13-,14?/m1/s1
• InChIKey: QKGHBQJLEHAMKJ-RQICVUQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4,6-tris(acetyloxy)-5-azidooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4,6-tris(acetyloxy)-5-azidooxan-2-yl]methyl acetate
• Synonyms: 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose; 2-Azido-2-deoxy-D-galactopyranose 1,3,4,6-Tetraacetate; 2-Azido-2-deoxy-1,3,4,6-tetra-O-acetyl-D-galactopyranose

Database IDs

• CAS Number: 84278-00-2
• PubChem SID: 162255137
• PubChem CID: 10904812

CALCULATED PROPERTIES

• Acid pKa: 12.492443
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): -0.46173882
• LogD (pH = 7.4): -0.4617423
• Log P: -0.34769315
• Molar Refractivity: 78.8219 cm^3
• Polarizability: 32.2624 Å^3
• Polar Surface Area: 143.86 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol; Ethyl Acetate,
• Apperance: White Crystalline Solid
• Melting Point: 113-114°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

REFERENCES

• Koeller, K., et al.: Bioorg. Med. Chem., 8, 1017 (2000)