(2R,3R,4R,5S)-4,5-bis(acetyloxy)-2-methyloxolan-3-yl acetate

• ChemBase ID: 166020
• Molecular Formular: C11H16O7
• Molecular Mass: 260.24054
• Monoisotopic Mass: 260.08960285
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1OC(=O)C)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1[C@H](OC(=O)C)O[C@@H]([C@H]1OC(=O)C)C
• InChI: InChI=1S/C11H16O7/c1-5-9(16-6(2)12)10(17-7(3)13)11(15-5)18-8(4)14/h5,9-11H,1-4H3/t5-,9-,10-,11+/m1/s1
• InChIKey: NXEJETQVUQAKTO-PRTGYXNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S)-4,5-bis(acetyloxy)-2-methyloxolan-3-yl acetate
• IUPAC Traditional name: (2R,3R,4R,5S)-4,5-bis(acetyloxy)-2-methyloxolan-3-yl acetate
• Synonyms: 1,2,3-Tri-O-acetyl-5-deoxy-β-D-ribofuranose; 5-Deoxy-β-D-ribofuranose Triacetate; 5-Deoxy-1,2,3-triacetyl-5-deoxy-β-D-ribose

Database IDs

• CAS Number: 62211-93-2
• PubChem SID: 162260153
• PubChem CID: 11821332

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.06808192
• LogD (pH = 7.4): 0.06808192
• Log P: 0.06808192
• Molar Refractivity: 55.8717 cm^3
• Polarizability: 23.490639 Å^3
• Polar Surface Area: 88.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Water
• Apperance: White Solid
• Melting Point: 64-66°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D281900

Intermediate in the preparation of Cepecitabine.

REFERENCES

• Wang, G., et al.: J. Med. Chem., 43, 2566 (2000)