(4S,5R)-2-[(hydroxyimino)methyl]-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 160691
• Molecular Formular: C6H11NO5
• Molecular Mass: 177.15524
• Monoisotopic Mass: 177.06372246
• SMILES: [C@H]1([C@H](OC(C1O)/C=N/O)CO)O
• Canonical SMILES: O/N=C/C1O[C@@H]([C@H](C1O)O)CO
• InChI: InChI=1S/C6H11NO5/c8-2-4-6(10)5(9)3(12-4)1-7-11/h1,3-6,8-11H,2H2/t3?,4-,5?,6-/m1/s1
• InChIKey: LOWIEQVCSWOMAE-MUTXJXMQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5R)-2-[(hydroxyimino)methyl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (4S,5R)-2-[(hydroxyimino)methyl]-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 2,5-Anhydro-D-mannofuranoseoxime; 2,5-Anhydro D-Mannose Oxime, Technical grade

Database IDs

• CAS Number: 127676-61-3
• PubChem SID: 162254826
• PubChem CID: 71313433

CALCULATED PROPERTIES

• Acid pKa: 7.173928
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.4065323
• LogD (pH = 7.4): -2.8229852
• Log P: -2.3971772
• Molar Refractivity: 37.6572 cm^3
• Polarizability: 15.271282 Å^3
• Polar Surface Area: 102.51 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Viscous Oil

DETAILS

Toronto Research Chemicals - A653270

This compound contains at least 65% of the oxime along with the analogous aldehyde and acetal.2,5-Anhydro D-Mannose Oxime is used in the preparation of C-(D-glycopyranosyl)ethylamines and C-(D-glycofuranosyl)methylamines as potential glycosidase inhibitor

REFERENCES

• Dale, M., et al.: Biochemistry, 24, 3530 (1985)
• Dumas, D., et al.: Bioorg. Med. Chem. Lett., 1992, 2, 33 (1985)