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

• ChemBase ID: 179624
• Molecular Formular: C18H26N2O10
• Molecular Mass: 430.40644
• Monoisotopic Mass: 430.15874504
• SMILES: C1=C(O[C@H]([C@@H]([C@H]1N)NC(=O)C)[C@H]([C@@H](COC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC
• Canonical SMILES: COC(=O)C1=C[C@H](N)[C@H]([C@@H](O1)[C@H]([C@H](OC(=O)C)COC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C18H26N2O10/c1-8(21)20-15-12(19)6-13(18(25)26-5)30-17(15)16(29-11(4)24)14(28-10(3)23)7-27-9(2)22/h6,12,14-17H,7,19H2,1-5H3,(H,20,21)/t12-,14+,15+,16-,17+/m0/s1
• InChIKey: LWRWOGLOMFAFCK-BYHHXJKWSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 139110-70-6
• PubChem SID: 164235534
• PubChem CID: 71753011

CALCULATED PROPERTIES

• Acid pKa: 13.245526
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -4.905024
• LogD (pH = 7.4): -3.4168046
• Log P: -2.09243
• Molar Refractivity: 97.9918 cm^3
• Polarizability: 39.71511 Å^3
• Polar Surface Area: 169.55 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Water
• Apperance: Low Melting Yellow Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - Z148010

A synthetic precursor of Zanamivir (Z148000), as antiviral agents against influenza virus.

REFERENCES

• Taylor, N., et al.: J. Med. Chem., 41, 798 (1998)
• Watson, K., et al.: Bioorg. Med. Chem. Lett., 14, 1589 (1998)
• Ying, L., et al.: ChemBioChem., 6, 1857 (1998)