(3aR,5S,6aS)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol

• ChemBase ID: 167748
• Molecular Formular: C12H20O6
• Molecular Mass: 260.2836
• Monoisotopic Mass: 260.12598836
• SMILES: C1(O)[C@@H](C2COC(O2)(C)C)O[C@@H]2OC(O[C@@H]12)(C)C
• Canonical SMILES: OC1[C@H](O[C@H]2[C@H]1OC(O2)(C)C)C1COC(O1)(C)C
• InChI: InChI=1S/C12H20O6/c1-11(2)14-5-6(16-11)8-7(13)9-10(15-8)18-12(3,4)17-9/h6-10,13H,5H2,1-4H3/t6?,7?,8-,9+,10-/m1/s1
• InChIKey: KEJGAYKWRDILTF-PGQYJIMISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,5S,6aS)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-tetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol
• IUPAC Traditional name: (3aR,5S,6aS)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• Synonyms: 1,2:5,6-Bis-O-(1-methylethylidene)-α-D-glucofuranose; 1,2:5,6-Di-O-isopropylidene-D-glucose; D-Glucose Diacetonide; Diacetoneglucose; Glucose Bisacetonide; NSC 1223; DAG.; 1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose; 1,2:5,6-Bis-O-(1-methylethylidene)-α-D-allofuranose; 1,2:5,6-Diacetone-D-allofuranose; Diacetone-D-allofuranose; 1,2:5,6-Di-O-isopropylidene-α-D-allofuranose

Database IDs

• CAS Number: 582-52-5; 2595-05-3
• PubChem SID: 162261881
• PubChem CID: 2784000

CALCULATED PROPERTIES

• Acid pKa: 12.956559
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 0.47231
• LogD (pH = 7.4): 0.4723088
• Log P: 0.47231
• Molar Refractivity: 60.3374 cm^3
• Polarizability: 24.877773 Å^3
• Polar Surface Area: 66.38 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White to Off-White Solid
• Melting Point: 105-108°C; 75-77°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D455750

Protected α-D-Allofuranose

REFERENCES

• Beil., 31, 155
• Carlucci, M., et al.: Biochem., 48, 10882 (2009)
• Muhizi, T., et al.: J. Agric. Food Chem., 57, 8770 (2009)