methyl (2S,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]oxy}-6-[(2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate

• ChemBase ID: 179113
• Molecular Formular: C30H32F3NO15
• Molecular Mass: 703.5679896
• Monoisotopic Mass: 703.17240399
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@](O1)(Oc1ccc2c(c1)oc(=O)cc2C(F)(F)F)C(=O)OC)OC(=O)C)NC(=O)C)C([C@H](COC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@@]1(Oc2ccc3c(c2)oc(=O)cc3C(F)(F)F)C[C@@H](OC(=O)C)[C@H]([C@@H](O1)C([C@@H](OC(=O)C)COC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C30H32F3NO15/c1-13(35)34-25-22(44-15(3)37)11-29(28(41)42-6,48-18-7-8-19-20(30(31,32)33)10-24(40)47-21(19)9-18)49-27(25)26(46-17(5)39)23(45-16(4)38)12-43-14(2)36/h7-10,22-23,25-27H,11-12H2,1-6H3,(H,34,35)/t22-,23-,25+,26?,27+,29+/m0/s1
• InChIKey: OSBBVRZZLWPPFC-HMIXGCIYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-{[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]oxy}-6-[(2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-{[2-oxo-4-(trifluoromethyl)chromen-7-yl]oxy}-6-[(2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• Synonyms: N-Acetyl-2-O-[2-oxo-4-(trifluoromethyl)-2H-1-benzopyran-7-yl]-α-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate; 4-Trifluoromethylumbelliferyl Tetra-O-acetylated α-D-N-Acetylneuraminate Methyl Ester

Database IDs

• CAS Number: 195210-09-4
• PubChem SID: 164235023
• PubChem CID: 71752772

CALCULATED PROPERTIES

• Acid pKa: 12.618603
• H Acceptors: 9
• H Donor: 1
• LogD (pH = 5.5): 1.1545447
• LogD (pH = 7.4): 1.1545429
• Log P: 1.1545453
• Molar Refractivity: 150.1215 cm^3
• Polarizability: 59.999615 Å^3
• Polar Surface Area: 205.36 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - T792030

An intermediate for the synthesis of a fluorogenic substrate used to measure sialidase activity.

REFERENCES

• Engstler, M., et al.: Anal. Biochem., 250, 176 (1997)