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

• ChemBase ID: 172460
• Molecular Formular: C5H8O5
• Molecular Mass: 148.11402
• Monoisotopic Mass: 148.03717336
• SMILES: C1(O)[C@@H](CO)OC(=O)[C@H]1O
• 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-/m1/s1
• InChIKey: CUOKHACJLGPRHD-BSDROHESSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 15384-34-6
• PubChem SID: 164228370
• PubChem CID: 45039673

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

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Crystalline Solid
• Melting Point: 114°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L490000

D-Lyxono-1,4-lactone is used for synthesis of 1,4-dideoxy-1,4-imino-L-arabinitol, a glucosidase inhibitor with in vitro antiviral activity.

REFERENCES

• Mitrakou, A., et al.: Diab. Med., 15, 657 (1998)
• Scott, L., et al.: Drugs, 59, 521 (1998)
• Vasella, A., et al.: Curr. Opin. Chem. Biol., 6, 619 (1998)
• Kato, A., et al.: J. Med. Chem., 48, 2036 (1998)