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

• ChemBase ID: 174018
• Molecular Formular: C11H21NO8
• Molecular Mass: 295.28634
• Monoisotopic Mass: 295.12671664
• SMILES: C1[C@](O[C@H]([C@@H]([C@@H]1O)N)[C@@H]([C@@H](CO)O)O)(C(=O)OC)OC
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@@](OC)(C[C@H]([C@H]1N)O)C(=O)OC)O)O
• InChI: InChI=1S/C11H21NO8/c1-18-10(17)11(19-2)3-5(14)7(12)9(20-11)8(16)6(15)4-13/h5-9,13-16H,3-4,12H2,1-2H3/t5-,6+,7+,8+,9+,11-/m0/s1
• InChIKey: FAXUBNUGEDSQNU-PFQGKNLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,4S,5R,6R)-5-amino-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,4S,5R,6R)-5-amino-4-hydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• Synonyms: Neuraminic Acid β-Methylglycoside Methyl Ester; Methyl 5-Amino-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosidonic Acid Methyl Ester; 2-O-Methyl β-Neuraminic Acid Methyl Ester

Database IDs

• CAS Number: 56070-37-2
• PubChem SID: 164229928
• PubChem CID: 13671164

CALCULATED PROPERTIES

• Acid pKa: 12.881074
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -5.3339195
• LogD (pH = 7.4): -3.766551
• Log P: -2.5937636
• Molar Refractivity: 63.8579 cm^3
• Polarizability: 26.71254 Å^3
• Polar Surface Area: 151.7 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellowish Solid

Safety Information

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

DETAILS

Toronto Research Chemicals - M323210

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)