(3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol

• ChemBase ID: 162302
• Molecular Formular: C6H10O3
• Molecular Mass: 130.1418
• Monoisotopic Mass: 130.06299418
• SMILES: C1[C@@H]2[C@H](OC1)OCC2O
• Canonical SMILES: OC1CO[C@@H]2[C@H]1CCO2
• InChI: InChI=1S/C6H10O3/c7-5-3-9-6-4(5)1-2-8-6/h4-7H,1-3H2/t4-,5?,6+/m0/s1
• InChIKey: RCDXYCHYMULCDZ-NOWQFEBASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
• IUPAC Traditional name: (3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol
• Synonyms: (3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol; (3aS,6aR)-Hexahydro-furo[2,3-b]furan-3-ol; (rel-R,S)-Bisfuran Alcohol (Mixture of Diastereomers)

Database IDs

• PubChem SID: 162256437
• PubChem CID: 58186656

CALCULATED PROPERTIES

• Acid pKa: 14.000419
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.22748579
• LogD (pH = 7.4): -0.2274859
• Log P: -0.22748578
• Molar Refractivity: 30.1305 cm^3
• Polarizability: 12.405186 Å^3
• Polar Surface Area: 38.69 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Pale Yellow Oil

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B436000

An intermediate in the preparation of protease inhibitors used to treat HIV.

REFERENCES

• Tie, Y., et al.: J. Mol. Biol., 338, 341 (2004)
• Miller, J., et al.: Bioorg. Med. Chem. Lett., 15, 3496 (2004)
• Surleraux, D., et al.: J. Med. Chem., 48, 1813 (2004)