(3S,5R)-5-methyloxolane-2,3,4-triol

• ChemBase ID: 166011
• Molecular Formular: C5H10O4
• Molecular Mass: 134.1305
• Monoisotopic Mass: 134.0579088
• SMILES: C1(O)[C@H](OC([C@H]1O)O)C
• Canonical SMILES: C[C@H]1OC([C@H](C1O)O)O
• InChI: InChI=1S/C5H10O4/c1-2-3(6)4(7)5(8)9-2/h2-8H,1H3/t2-,3?,4+,5?/m1/s1
• InChIKey: MKMRBXQLEMYZOY-QNLMJMMGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,5R)-5-methyloxolane-2,3,4-triol
• IUPAC Traditional name: (3S,5R)-5-methyloxolane-2,3,4-triol
• Synonyms: 5-Deoxy-D-ribose

Database IDs

• CAS Number: 13039-75-3
• PubChem SID: 162260144
• PubChem CID: 59510450

CALCULATED PROPERTIES

• Acid pKa: 11.310508
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.255295
• LogD (pH = 7.4): -1.2553476
• Log P: -1.2552943
• Molar Refractivity: 28.4172 cm^3
• Polarizability: 11.923472 Å^3
• Polar Surface Area: 69.92 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D252015

Used in the process for preparing Capecitabine and β-trialkyl carbonate nucleosides.

REFERENCES

• Shimma, N., et al.: Bioorg. Med. Chem., 8, 1697 (2000)