methyl (2R,4S,5R,6R)-2-(benzyloxy)-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate

• ChemBase ID: 159166
• Molecular Formular: C19H27NO9
• Molecular Mass: 413.41898
• Monoisotopic Mass: 413.16858145
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@](O1)(OCc1ccccc1)C(=O)OC)O)NC(=O)C)[C@@H]([C@@H](CO)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@](OCc2ccccc2)(C[C@H]([C@H]1NC(=O)C)O)C(=O)OC)O)O
• InChI: InChI=1S/C19H27NO9/c1-11(22)20-15-13(23)8-19(18(26)27-2,28-10-12-6-4-3-5-7-12)29-17(15)16(25)14(24)9-21/h3-7,13-17,21,23-25H,8-10H2,1-2H3,(H,20,22)/t13-,14+,15+,16+,17+,19+/m0/s1
• InChIKey: RBYASKWXZPHFPT-DWYCWXKBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,4S,5R,6R)-2-(benzyloxy)-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,4S,5R,6R)-2-(benzyloxy)-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• Synonyms: Benzyl 5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosidonic Acid Methyl Ester; N-Acetyl-2-O-benzyl-neuraminic Acid Methyl Ester, 85%

Database IDs

• PubChem SID: 162253301
• PubChem CID: 71312836

CALCULATED PROPERTIES

• Acid pKa: 12.650681
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -1.0504445
• LogD (pH = 7.4): -1.0504462
• Log P: -1.0504439
• Molar Refractivity: 97.9143 cm^3
• Polarizability: 39.574986 Å^3
• Polar Surface Area: 154.78 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 80-82°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A170805

Neuraminic Acid derivative.