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

• ChemBase ID: 179625
• Molecular Formular: C12H18N4O7
• Molecular Mass: 330.29392
• Monoisotopic Mass: 330.11754894
• SMILES: C1=C(O[C@H]([C@@H]([C@@H]1N=[N+]=[N-])NC(=O)C)[C@@H]([C@@H](CO)O)O)C(=O)OC
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1OC(=C[C@H]([C@H]1NC(=O)C)N=[N+]=[N-])C(=O)OC)O)O
• InChI: InChI=1S/C12H18N4O7/c1-5(18)14-9-6(15-16-13)3-8(12(21)22-2)23-11(9)10(20)7(19)4-17/h3,6-7,9-11,17,19-20H,4H2,1-2H3,(H,14,18)/t6-,7-,9-,10-,11-/m1/s1
• InChIKey: MMLUEZXBKJUPII-JBSYKWBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3R,4R)-4-azido-3-acetamido-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• IUPAC Traditional name: methyl (4R,5R,6R)-4-azido-5-acetamido-6-[(1R,2R)-1,2,3-trihydroxypropyl]-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; Zanamivir Azide Methyl Ester

Database IDs

• CAS Number: 152178-79-5
• PubChem SID: 164235535
• PubChem CID: 71753012

CALCULATED PROPERTIES

• Acid pKa: 12.62308
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.6026266
• LogD (pH = 7.4): -2.6026282
• Log P: -2.4885802
• Molar Refractivity: 75.1723 cm^3
• Polarizability: 29.013716 Å^3
• Polar Surface Area: 154.75 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - Z148030

An intermediate used in the preparation of Zanamivir derivatives.

REFERENCES

• Andrews, D., et al.: Eur. J. Med. Chem., 34, 563 (1999)
• Altamore, T., et al.: Bioorg. Med. Chem., 14, 1126 (1999)