methyl (4S,5R,6R)-2,4-bis(acetyloxy)-5-acetamido-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate

• ChemBase ID: 159379
• Molecular Formular: C22H31NO14
• Molecular Mass: 533.47984
• Monoisotopic Mass: 533.17445468
• SMILES: [C@@H]1([C@@H]([C@@H](CC(O1)(C(=O)OC)OC(=O)C)OC(=O)C)NC(=O)C)[C@@H]([C@H](COC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)C1(OC(=O)C)C[C@@H](OC(=O)C)[C@H]([C@@H](O1)[C@@H]([C@@H](OC(=O)C)COC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C22H31NO14/c1-10(24)23-18-16(33-12(3)26)8-22(21(30)31-7,36-15(6)29)37-20(18)19(35-14(5)28)17(34-13(4)27)9-32-11(2)25/h16-20H,8-9H2,1-7H3,(H,23,24)/t16-,17-,18+,19+,20+,22?/m0/s1
• InChIKey: MFDZYSKLMAXHOV-CENYPAOVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4S,5R,6R)-2,4-bis(acetyloxy)-5-acetamido-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (4S,5R,6R)-2,4-bis(acetyloxy)-5-acetamido-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• Synonyms: 5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic Acid Methyl Ester 2,4,7,8,9-Pentaacetate; N-Acetylneuraminic Acid Methyl Ester 2,4,7,8,9-Pentaacetate

Database IDs

• CAS Number: 73208-82-9
• PubChem SID: 162253514
• PubChem CID: 11827581

CALCULATED PROPERTIES

• Acid pKa: 12.790502
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -1.212417
• LogD (pH = 7.4): -1.212418
• Log P: -1.2124164
• Molar Refractivity: 114.308 cm^3
• Polarizability: 47.5552 Å^3
• Polar Surface Area: 196.13 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: White Foam

DETAILS

Toronto Research Chemicals - A187030

Protected Neuraminic Acid derivative.

REFERENCES

• Kaneko, H., et al.: Chem. Pharm. Bull., 45, 951 (1997)
• Suzuki, K., et al.: Bioorg. Med. Chem. Lett., 19, 5105 (1997)