[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-azido-6-hydroxyoxan-2-yl]methyl acetate

• ChemBase ID: 178850
• Molecular Formular: C12H17N3O8
• Molecular Mass: 331.27868
• Monoisotopic Mass: 331.10156452
• SMILES: [C@H]1([C@@H]([C@@H](C(O[C@H]1COC(=O)C)O)N=[N+]=[N-])OC(=O)C)OC(=O)C
• Canonical SMILES: [N-]=[N+]=N[C@@H]1C(O)O[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)COC(=O)C
• InChI: InChI=1S/C12H17N3O8/c1-5(16)20-4-8-10(21-6(2)17)11(22-7(3)18)9(14-15-13)12(19)23-8/h8-12,19H,4H2,1-3H3/t8-,9-,10+,11-,12?/m1/s1
• InChIKey: PLVPDCSPQJIUQM-OZRWLHRGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-azido-6-hydroxyoxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-azido-6-hydroxyoxan-2-yl]methyl acetate
• Synonyms: 2-Azido-2-deoxy-D-galactose 3,4,6-Triacetate; 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-D-galactose

Database IDs

• CAS Number: 83025-10-9
• PubChem SID: 164234760
• PubChem CID: 15322432

CALCULATED PROPERTIES

• Acid pKa: 11.511985
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -0.90286463
• LogD (pH = 7.4): -0.9028977
• Log P: -0.78881854
• Molar Refractivity: 69.6704 cm^3
• Polarizability: 28.40928 Å^3
• Polar Surface Area: 137.79 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White Solid

REFERENCES

• Barchi, J., et al.: Bioorg. Med. Chem. Lett., 5, 711 (1995)