(4S,5S,6S)-4-methoxy-4,6-dimethyloxane-2,5-diol

• ChemBase ID: 164591
• Molecular Formular: C8H16O4
• Molecular Mass: 176.21024
• Monoisotopic Mass: 176.10485899
• SMILES: [C@H]1([C@@](CC(O[C@H]1C)O)(C)OC)O
• Canonical SMILES: CO[C@@]1(C)CC(O)O[C@H]([C@@H]1O)C
• InChI: InChI=1S/C8H16O4/c1-5-7(10)8(2,11-3)4-6(9)12-5/h5-7,9-10H,4H2,1-3H3/t5-,6?,7-,8-/m0/s1
• InChIKey: YHVUVJYEERGYNU-BHQGJQQGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5S,6S)-4-methoxy-4,6-dimethyloxane-2,5-diol
• IUPAC Traditional name: (4S,5S,6S)-4-methoxy-4,6-dimethyloxane-2,5-diol
• Synonyms: 2,6-Dideoxy-3-C-methyl-3-O-methyl-ribo-hexose; Cladinose

Database IDs

• CAS Number: 470-12-2
• PubChem SID: 162258726
• PubChem CID: 12303304

CALCULATED PROPERTIES

• Acid pKa: 12.28822
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.06128809
• LogD (pH = 7.4): -0.061293628
• Log P: -0.061288018
• Molar Refractivity: 42.2584 cm^3
• Polarizability: 17.435331 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C557480

A hexose sugar commonly associated with the macrolide ring of relevant antibiotics.

REFERENCES

• Darrington, R., et al.: J. Pharm. Sci., 93, 838 (2004)
• Randolph, J., et al.: J. Med. Chem., 47, 1085 (2004)
• Butler, M., et al.: Environ. Sci. Technol., 39, 2301 (2004)
• Vazquez-Laslop, N., et al.: Mol. Cell., 30, 190 (2004)