(2S,4S,5R,6R)-5-amino-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 174017
• Molecular Formular: C10H19NO8
• Molecular Mass: 281.25976
• Monoisotopic Mass: 281.11106657
• SMILES: C1[C@](O[C@H]([C@@H]([C@@H]1O)N)[C@@H]([C@@H](CO)O)O)(C(=O)O)OC
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@@](OC)(C[C@H]([C@H]1N)O)C(=O)O)O)O
• InChI: InChI=1S/C10H19NO8/c1-18-10(9(16)17)2-4(13)6(11)8(19-10)7(15)5(14)3-12/h4-8,12-15H,2-3,11H2,1H3,(H,16,17)/t4-,5+,6+,7+,8+,10-/m0/s1
• InChIKey: OMVQZDUAKZZNEF-APDUKXCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5R,6R)-5-amino-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2S,4S,5R,6R)-5-amino-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: Neuraminic Acid β-Methylglycoside; Methyl β-Neuraminic Acid

Database IDs

• CAS Number: 56144-08-2
• PubChem SID: 164229927
• PubChem CID: 10934861

CALCULATED PROPERTIES

• Acid pKa: 2.8035867
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -5.0031896
• LogD (pH = 7.4): -5.0301113
• Log P: -5.003483
• Molar Refractivity: 59.0888 cm^3
• Polarizability: 24.678326 Å^3
• Polar Surface Area: 162.7 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: >160°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M323200

A useful synthetic intermediate for the preparation of aminde-linked sialooligomers. A naturally occurring δ-Amino Acid.

REFERENCES

• Mester, L., et al.: J. Carbohydr., Nucleosides, Nucleotides, 4(5)
• 249 (5)
• Szabo, L., et al.: J. Org. Chem., 63, 1074 (1998)