(2S,3R,4S,6S)-6-(hydroxymethyl)-2-methoxyoxane-3,4-diol

• ChemBase ID: 173518
• Molecular Formular: C7H14O5
• Molecular Mass: 178.18306
• Monoisotopic Mass: 178.08412355
• SMILES: C1[C@@H]([C@@H]([C@H](O[C@H]1CO)OC)O)O
• Canonical SMILES: CO[C@H]1O[C@@H](CO)C[C@@H]([C@@H]1O)O
• InChI: InChI=1S/C7H14O5/c1-11-7-6(10)5(9)2-4(3-8)12-7/h4-10H,2-3H2,1H3/t4-,5-,6+,7-/m0/s1
• InChIKey: ARNZRNVPEASSLV-YTLHQDLWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,6S)-6-(hydroxymethyl)-2-methoxyoxane-3,4-diol
• IUPAC Traditional name: (2S,3R,4S,6S)-6-(hydroxymethyl)-2-methoxyoxane-3,4-diol
• Synonyms: Methyl 4-Deoxy-α-D-xylohexopyranoside; Methyl 4-Deoxy-α-D-glucopyranoside

Database IDs

• CAS Number: 13241-00-4
• PubChem SID: 164229428
• PubChem CID: 14311532

CALCULATED PROPERTIES

• Acid pKa: 12.442193
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.5991181
• LogD (pH = 7.4): -1.5991219
• Log P: -1.599118
• Molar Refractivity: 39.5775 cm^3
• Polarizability: 16.30861 Å^3
• Polar Surface Area: 79.15 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - M296210

This compound has been shown to stimulate gustatory receptors, specifically those responsible for sweet taste in mammalian biochemical studies. It is also an intermediate for the synthesis of 4-Deoxy-D-glucose.

REFERENCES

• Lee, C., et al.: J. Sci. Food Agr., 26, 1513 (1975)
• Mosi, R., et al.: Biochem. J., 338, 251 (1975)