(3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-one

• ChemBase ID: 171909
• Molecular Formular: C8H12O5
• Molecular Mass: 188.17788
• Monoisotopic Mass: 188.06847348
• SMILES: [C@H]12[C@H](OC(O1)(C)C)[C@@H](OC2=O)CO
• Canonical SMILES: OC[C@@H]1OC(=O)[C@H]2[C@@H]1OC(O2)(C)C
• InChI: InChI=1S/C8H12O5/c1-8(2)12-5-4(3-9)11-7(10)6(5)13-8/h4-6,9H,3H2,1-2H3/t4-,5+,6+/m0/s1
• InChIKey: NHHKFJCWLPPNCN-KVQBGUIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-one
• IUPAC Traditional name: (3aR,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyl-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• Synonyms: 2,3-O-(1-Methylethylidene)-L-lyxonic Acid γ-Lactone; 2,3-O-Isopropylidene-L-lyxono-1,4-lactone

Database IDs

• CAS Number: 152006-17-2
• PubChem SID: 164227819
• PubChem CID: 9990017

CALCULATED PROPERTIES

• Acid pKa: 14.5634775
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.41251364
• LogD (pH = 7.4): -0.41251364
• Log P: -0.4125136
• Molar Refractivity: 41.0233 cm^3
• Polarizability: 16.957924 Å^3
• Polar Surface Area: 64.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 95-97°C

DETAILS

Toronto Research Chemicals - I868650

Intermediate in the synthesis of the α-L-fucosidase inhibitor, Deoxyfuconojirimycin.

REFERENCES

• Evans, G., et al.: J. Med. Chem., 46, 5271 (2003)
• Lewandowicz, A., et al.: J. Biol. Chem., 280, 30320 (2003)