methyl (2S,3S,4R,5S)-3,4,5-tris(acetyloxy)oxolane-2-carboxylate

• ChemBase ID: 177521
• Molecular Formular: C12H16O9
• Molecular Mass: 304.25004
• Monoisotopic Mass: 304.07943209
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1OC(=O)C)C(=O)OC)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C12H16O9/c1-5(13)18-8-9(11(16)17-4)21-12(20-7(3)15)10(8)19-6(2)14/h8-10,12H,1-4H3/t8-,9+,10-,12-/m1/s1
• InChIKey: WKPDVIUFXMUXNU-DTHBNOIPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4R,5S)-3,4,5-tris(acetyloxy)oxolane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4R,5S)-3,4,5-tris(acetyloxy)oxolane-2-carboxylate
• Synonyms: β-D-Ribofuranuronic Acid Methyl Ester 1,2,3-Triacetate; β-D-Ribofuranuronic Acid Methyl Ester Triacetate

Database IDs

• CAS Number: 68673-84-7
• PubChem SID: 164233431
• PubChem CID: 10828323

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.51265943
• LogD (pH = 7.4): -0.51265943
• Log P: -0.51265943
• Molar Refractivity: 62.0519 cm^3
• Polarizability: 26.24724 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R415900

Used in the synthesis of tritiated 2-chloro-N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide, a potent, selective A3 adenosine receptor agonist, a radiolabeling agent.

REFERENCES

• Hutchison, A., et al.: J. Pharmacol. Exp. Ther., 251, 47 (1989)
• Cristalli, G., et al.: J. Med. Chem., 37, 1720 (1989)
• Cristalli, G., et al.: ChemMedChem., 2, 260 (1989)