(3S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one

• ChemBase ID: 172461
• Molecular Formular: C5H8O5
• Molecular Mass: 148.11402
• Monoisotopic Mass: 148.03717336
• SMILES: C1([C@@H](OC(=O)[C@H]1O)CO)O
• Canonical SMILES: OC[C@@H]1OC(=O)[C@H](C1O)O
• InChI: InChI=1S/C5H8O5/c6-1-2-3(7)4(8)5(9)10-2/h2-4,6-8H,1H2/t2-,3?,4-/m0/s1
• InChIKey: CUOKHACJLGPRHD-QNVNXEQISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
• IUPAC Traditional name: (3S,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one
• Synonyms: L-Lyxonic Acid γ-Lactone; L-Lyxono-1,4-lactone

Database IDs

• CAS Number: 104196-15-8
• PubChem SID: 164228371
• PubChem CID: 71749868

CALCULATED PROPERTIES

• Acid pKa: 11.633838
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.1149385
• LogD (pH = 7.4): -2.1149635
• Log P: -2.1149383
• Molar Refractivity: 28.8163 cm^3
• Polarizability: 12.117866 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L490005

L-Lyxono-1,4-lactone is used in the synthesis of 2-Acetamido-1,4-imino-1,2,4-trideoxy-L-arabinitol LABNAc, a potent pyrrolidine inhibitor of hexosaminidases.

REFERENCES

• Woynarowska, B., et al.: Anticancer, Res., 12, 161 (1992)
• Reddi, A., et al.: Cancer Lett., 158, 61 (1992)
• Liu, J., et al.: Chem. Biol., 8, 701 (1992)