5,5-diethoxypentyl methanesulfonate

• ChemBase ID: 167265
• Molecular Formular: C10H22O5S
• Molecular Mass: 254.34368
• Monoisotopic Mass: 254.1187948
• SMILES: C(CCCCOS(=O)(=O)C)(OCC)OCC
• Canonical SMILES: CCOC(OCC)CCCCOS(=O)(=O)C
• InChI: InChI=1S/C10H22O5S/c1-4-13-10(14-5-2)8-6-7-9-15-16(3,11)12/h10H,4-9H2,1-3H3
• InChIKey: BKQDXUHOGXVKGP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5,5-diethoxypentyl methanesulfonate
• IUPAC Traditional name: 5,5-diethoxypentyl methanesulfonate
• Synonyms: 5,5-Diethoxy-1-pentanol 1-Methanesulfonate; 5,5-Diethoxy-1-(methylsulfonyloxy)pentane

Database IDs

• CAS Number: 202577-28-4
• PubChem SID: 162261398
• PubChem CID: 21264494

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 1.1563197
• LogD (pH = 7.4): 1.1563197
• Log P: 1.1563197
• Molar Refractivity: 61.557 cm^3
• Polarizability: 25.481812 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate

DETAILS

Toronto Research Chemicals - D441910

Used in the syntheses of deoxynojirimycin derivatives which inhibit glucosylceramidase in vitro as well as in melanoma cells and macrophages.

REFERENCES

• Beutler, E., et al.: Science, 256, 794 (1992)
• Platt, F., et al.: J. Biol. Chem., 269, 8362 (1992)
• Hollak, C., et al.: J. Clin. Inves., 93, 1288 (1992)