methyl (2R,3R,4R)-4-azido-3-acetamido-2-[(1R,2R)-1,2,3-tris(acetyloxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate

• ChemBase ID: 179626
• Molecular Formular: C18H24N4O10
• Molecular Mass: 456.40396
• Monoisotopic Mass: 456.14924299
• SMILES: C1=C(O[C@H]([C@@H]([C@@H]1N=[N+]=[N-])NC(=O)C)[C@H]([C@@H](COC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC
• Canonical SMILES: [N-]=[N+]=N[C@@H]1C=C(O[C@H]([C@@H]1NC(=O)C)[C@H]([C@H](OC(=O)C)COC(=O)C)OC(=O)C)C(=O)OC
• InChI: InChI=1S/C18H24N4O10/c1-8(23)20-15-12(21-22-19)6-13(18(27)28-5)32-17(15)16(31-11(4)26)14(30-10(3)25)7-29-9(2)24/h6,12,14-17H,7H2,1-5H3,(H,20,23)/t12-,14-,15-,16+,17-/m1/s1
• InChIKey: ANKWFOHGBMGGAL-FYNNLBNCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3R,4R)-4-azido-3-acetamido-2-[(1R,2R)-1,2,3-tris(acetyloxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate
• IUPAC Traditional name: methyl (4R,5R,6R)-4-azido-5-acetamido-6-[(1R,2R)-1,2,3-tris(acetyloxy)propyl]-5,6-dihydro-4H-pyran-2-carboxylate
• Synonyms: 5-(Acetylamino)-2,6-anhydro-4-azido-3,4,5-trideoxy-D-glycero-D-galacto-non-2-enonic Acid Methyl Ester 7,8,9-Triacetate; Zanamivir Azide Triacetate Methyl Ester

Database IDs

• CAS Number: 130525-58-5
• PubChem SID: 164235536
• PubChem CID: 71753013

CALCULATED PROPERTIES

• Acid pKa: 12.936282
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -1.2792503
• LogD (pH = 7.4): -1.2792507
• Log P: -1.1652039
• Molar Refractivity: 102.6268 cm^3
• Polarizability: 40.580505 Å^3
• Polar Surface Area: 172.96 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - Z148040

An intermediate used in the preparation of Zanamivir derivatives.

REFERENCES

• Smith, P., et al.: Eur. J. Med. Chem., 31, 143 (1996)
• Li, J., et al.: Bioorg. Med. Chem. Lett., 16, 5009 (1996)