(5S)-6-methyloxane-2,3,5-triol

• ChemBase ID: 179374
• Molecular Formular: C6H12O4
• Molecular Mass: 148.15708
• Monoisotopic Mass: 148.07355886
• SMILES: [C@@H]1(CC(C(OC1C)O)O)O
• Canonical SMILES: O[C@H]1CC(O)C(OC1C)O
• InChI: InChI=1S/C6H12O4/c1-3-4(7)2-5(8)6(9)10-3/h3-9H,2H2,1H3/t3?,4-,5?,6?/m0/s1
• InChIKey: KYPWIZMAJMNPMJ-NKEXCQMJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S)-6-methyloxane-2,3,5-triol
• IUPAC Traditional name: (5S)-6-methyloxane-2,3,5-triol
• Synonyms: 3,6-Dideoxy-D-arabino-hexose; 3,6-Dideoxy-D-mannose; D-Tyvelose; Tyvelose

Database IDs

• CAS Number: 5658-12-8
• PubChem SID: 164235284
• PubChem CID: 46783490

CALCULATED PROPERTIES

• Acid pKa: 11.433746
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.195335
• LogD (pH = 7.4): -1.1953747
• Log P: -1.1953346
• Molar Refractivity: 33.2826 cm^3
• Polarizability: 13.731559 Å^3
• Polar Surface Area: 69.92 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Waxy Solid
• Melting Point: 70-74°C

Safety Information

• Storage Condition: Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T948000

The unusual sugar Tyvelose is the immunodominant portion of the major larval glycoprotein antigens of Trichinella spiralis, which play an important role in generating immunity against the intestinal stages of infection.

REFERENCES

• Denkers, E., et al.: J. Immunol., 144, 3152 (1990)
• Greenspan, N., et al.: Immunol. Today, 13, 164 (1990)
• Robinson, K., et al.: Immunology, 86, 495 (1990)
• Ortega-Pierres, M., et al.: Parasite Immunol., 18, 273 (1990)