[(2R,3R)-3-(benzoyloxy)-4,4-difluoro-5-(methanesulfonyloxy)oxolan-2-yl]methyl benzoate

• ChemBase ID: 165899
• Molecular Formular: C20H18F2O8S
• Molecular Mass: 456.4139264
• Monoisotopic Mass: 456.06904498
• SMILES: [C@@H]1(C(C(O[C@@H]1COC(=O)c1ccccc1)OS(=O)(=O)C)(F)F)OC(=O)c1ccccc1
• Canonical SMILES: O=C(c1ccccc1)OC[C@H]1OC(C([C@@H]1OC(=O)c1ccccc1)(F)F)OS(=O)(=O)C
• InChI: InChI=1S/C20H18F2O8S/c1-31(25,26)30-19-20(21,22)16(29-18(24)14-10-6-3-7-11-14)15(28-19)12-27-17(23)13-8-4-2-5-9-13/h2-11,15-16,19H,12H2,1H3/t15-,16-,19?/m1/s1
• InChIKey: LIAQHZDWFACWFK-QNRNLVPOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R)-3-(benzoyloxy)-4,4-difluoro-5-(methanesulfonyloxy)oxolan-2-yl]methyl benzoate; (2R,3R)-2-[(benzoyloxy)methyl]-4,4-difluoro-5-(methanesulfonyloxy)oxolan-3-yl benzoate
• IUPAC Traditional name: [(2R,3R)-3-(benzoyloxy)-4,4-difluoro-5-(methanesulfonyloxy)oxolan-2-yl]methyl benzoate; (2R,3R)-2-[(benzoyloxy)methyl]-4,4-difluoro-5-(methanesulfonyloxy)oxolan-3-yl benzoate
• Synonyms: 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate 1-Methanesulfonate; 2-Deoxy-2,2-difluoro-D-erythro-ribofuranose-3,5-dibenzoate 1-Methanesulfonate; 2-Deoxy-2,2-difluoro-D-erythro-pentofuranose-3,5-dibenzoate-1-methanesulfonate

Database IDs

• CAS Number: 122111-11-9
• PubChem SID: 162260032
• PubChem CID: 10950541

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.9555373
• LogD (pH = 7.4): 3.9555373
• Log P: 3.9555373
• Molar Refractivity: 101.0629 cm^3
• Polarizability: 40.68842 Å^3
• Polar Surface Area: 105.2 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol; Methanol
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 66-74°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - D232790

Gemcitabine intermediate.

REFERENCES

• Balzarini, J., et al.: Biochem. Pharmacol., 1988, 37, 2847 (1988)
• Hertel, L., et al.: Cancer Res., 50, 4417 (1988)
• Marquez, V., et al.: J. Med. Chem., 33, 978 (1988)