6-(hydroxymethyl)thiane-2,3,4,5-tetrol

• ChemBase ID: 178543
• Molecular Formular: C6H12O5S
• Molecular Mass: 196.22148
• Monoisotopic Mass: 196.04054448
• SMILES: C1(C(C(C(C(S1)O)O)O)O)CO
• Canonical SMILES: OCC1SC(O)C(C(C1O)O)O
• InChI: InChI=1S/C6H12O5S/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2
• InChIKey: KNWYARBAEIMVMZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(hydroxymethyl)thiane-2,3,4,5-tetrol
• IUPAC Traditional name: 5-thio-D-glucose
• Synonyms: 5-Thio-L-galactopyranose; 5-Thio-L-galactose(α /β-Mixture)

Database IDs

• PubChem SID: 164234453
• PubChem CID: 307185

CALCULATED PROPERTIES

• Acid pKa: 12.410834
• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -2.6214085
• LogD (pH = 7.4): -2.6214125
• Log P: -2.6214085
• Molar Refractivity: 42.2742 cm^3
• Polarizability: 17.435747 Å^3
• Polar Surface Area: 101.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T344465

Novel conversion of aldopyranosides into 5-thioaldopyranosides via acyclic monothioacetals with inversion and retention of configuration at C-5. The strategy for L enantiomers was applied to the synthesis of thio-L-galactose with inhibitory effect of 5-th

REFERENCES

• Hashimoto, H., et al.: Carbohyd. Res., 282, 207 (1996)
• Atsushi, K., et al.: J. Med. Chem., 48, 2036 (1996)