(3S,5S,6S)-2-(hydroxymethyl)-6-(phenyldisulfanyl)oxane-3,4,5-triol

• ChemBase ID: 178561
• Molecular Formular: C12H16O5S2
• Molecular Mass: 304.38244
• Monoisotopic Mass: 304.04391561
• SMILES: O1[C@H]([C@@H](C([C@@H](C1CO)O)O)O)SSc1ccccc1
• Canonical SMILES: OCC1O[C@@H](SSc2ccccc2)[C@@H](C([C@@H]1O)O)O
• InChI: InChI=1S/C12H16O5S2/c13-6-8-9(14)10(15)11(16)12(17-8)19-18-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8?,9-,10?,11+,12+/m1/s1
• InChIKey: BRZSUUGAVYFRNR-PFOINOEHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,5S,6S)-2-(hydroxymethyl)-6-(phenyldisulfanyl)oxane-3,4,5-triol
• IUPAC Traditional name: (3S,5S,6S)-2-(hydroxymethyl)-6-(phenyldisulfanyl)oxane-3,4,5-triol
• Synonyms: 1-Deoxy-1-(phenyldithio)-β-D-glucopyranose; 1-Thio-β-D-glucopyranose 1-Benzenesulfenothioate; 1-Thio-β-D-glucose 1-Benzenesulfenothioate

Database IDs

• CAS Number: 1189134-15-3
• PubChem SID: 164234471
• PubChem CID: 71752529

CALCULATED PROPERTIES

• Acid pKa: 12.443769
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.39386043
• LogD (pH = 7.4): 0.39385656
• Log P: 0.3938605
• Molar Refractivity: 72.4758 cm^3
• Polarizability: 30.03792 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T350720

A thio-glucose derivative used in the enzymic elongation of the β(1→3)-glucan chain.

REFERENCES

• Montel, E. et al.: Aus. J. Chem., 62, 575 (2009)