(3'aS,6'R)-6'-(hydroxymethyl)-tetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxole]-4'-one

• ChemBase ID: 177523
• Molecular Formular: C11H16O5
• Molecular Mass: 228.24174
• Monoisotopic Mass: 228.09977361
• SMILES: [C@H]12C([C@H](OC1=O)CO)OC1(O2)CCCCC1
• Canonical SMILES: OC[C@H]1OC(=O)[C@@H]2C1OC1(O2)CCCCC1
• InChI: InChI=1S/C11H16O5/c12-6-7-8-9(10(13)14-7)16-11(15-8)4-2-1-3-5-11/h7-9,12H,1-6H2/t7-,8?,9+/m1/s1
• InChIKey: PPHFUIUOGMRDON-NBXIYJJMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3'aS,6'R)-6'-(hydroxymethyl)-tetrahydrospiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxole]-4'-one
• IUPAC Traditional name: (4'R,6'aS)-4'-(hydroxymethyl)-dihydro-3'aH-spiro[cyclohexane-1,2'-furo[3,4-d][1,3]dioxole]-6'-one
• Synonyms: 2,3-O-Cyclohexylidene-D-ribono-1,4-lactone; 2,3-O-Cyclohexylidene-D-ribonic Acid γ-lactone; D-Ribonolactone 2,3-Cyclohexyl Ketal

Database IDs

• CAS Number: 27304-20-7
• PubChem SID: 164233433
• PubChem CID: 71752072

CALCULATED PROPERTIES

• Acid pKa: 14.5634775
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.8420754
• LogD (pH = 7.4): 0.84207535
• Log P: 0.8420754
• Molar Refractivity: 52.7597 cm^3
• Polarizability: 21.702623 Å^3
• Polar Surface Area: 64.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Pale Solid

DETAILS

Toronto Research Chemicals - R416005

Protected D-Ribonolactone.

REFERENCES

• Wolfe, M., et al.: J. Med. Chem., 35, 1782 (1992)