methyl (3aR,4R,7aR)-2-methyl-4-[(1R,2R)-1,2,3-tris(acetyloxy)propyl]-3aH,4H,7aH-pyrano[3,4-d][1,3]oxazole-6-carboxylate

• ChemBase ID: 167679
• Molecular Formular: C18H23NO10
• Molecular Mass: 413.37592
• Monoisotopic Mass: 413.13219594
• SMILES: C1=C(O[C@H]([C@H]2[C@@H]1OC(=N2)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]2OC(=N[C@H]2[C@@H](O1)[C@H]([C@H](OC(=O)C)COC(=O)C)OC(=O)C)C
• InChI: InChI=1S/C18H23NO10/c1-8-19-15-12(26-8)6-13(18(23)24-5)29-17(15)16(28-11(4)22)14(27-10(3)21)7-25-9(2)20/h6,12,14-17H,7H2,1-5H3/t12-,14-,15-,16+,17-/m1/s1
• InChIKey: NHGHQTDLCDGYEQ-FYNNLBNCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3aR,4R,7aR)-2-methyl-4-[(1R,2R)-1,2,3-tris(acetyloxy)propyl]-3aH,4H,7aH-pyrano[3,4-d][1,3]oxazole-6-carboxylate
• IUPAC Traditional name: methyl (3aR,4R,7aR)-2-methyl-4-[(1R,2R)-1,2,3-tris(acetyloxy)propyl]-3aH,4H,7aH-pyrano[3,4-d][1,3]oxazole-6-carboxylate
• Synonyms: (3aR,4R,7aR)-3a,7a-Dihydro-2-methyl-4-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]-4H-pyrano[3,4-d]oxazole-6-carboxylic Acid Methyl Ester

Database IDs

• CAS Number: 78850-37-0
• PubChem SID: 162261812
• PubChem CID: 13847460

CALCULATED PROPERTIES

• Acid pKa: 15.734037
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): -0.5346072
• LogD (pH = 7.4): -0.53454065
• Log P: -0.5345398
• Molar Refractivity: 93.3459 cm^3
• Polarizability: 37.682957 Å^3
• Polar Surface Area: 136.02 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White Foam

DETAILS

Toronto Research Chemicals - D449365

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)