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

• ChemBase ID: 171877
• Molecular Formular: C9H14O6
• Molecular Mass: 218.20386
• Monoisotopic Mass: 218.07903817
• SMILES: [C@H]12C([C@H](OC1=O)[C@H](CO)O)OC(O2)(C)C
• Canonical SMILES: OC[C@@H]([C@H]1OC(=O)[C@@H]2C1OC(O2)(C)C)O
• InChI: InChI=1S/C9H14O6/c1-9(2)14-6-5(4(11)3-10)13-8(12)7(6)15-9/h4-7,10-11H,3H2,1-2H3/t4-,5+,6?,7+/m0/s1
• InChIKey: SSSBRIPVSPUGBC-NTIFKLMLSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 94840-08-1
• PubChem SID: 164227787
• PubChem CID: 71749597

CALCULATED PROPERTIES

• Acid pKa: 13.29883
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.0428486
• LogD (pH = 7.4): -1.0428491
• Log P: -1.0428486
• Molar Refractivity: 46.9858 cm^3
• Polarizability: 19.47009 Å^3
• Polar Surface Area: 85.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White to Off-White Solid
• Melting Point: 231-238°C (dec.)

DETAILS

Toronto Research Chemicals - I824740

Used in the synthesis of new hydrolyzable polyurethanes from l-gulonic acid-derived diols and diisocyanates.

REFERENCES

• Takamoto, T., et al.: Macromol. Biosci., 1, 215 (2001)