[(3aS,4R,6R,7R,7aR)-7-hydroxy-2,2-dimethyl-6-(4-nitrophenoxy)-hexahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate

• ChemBase ID: 175321
• Molecular Formular: C22H23NO9
• Molecular Mass: 445.41932
• Monoisotopic Mass: 445.13728132
• SMILES: [C@@H]12[C@@H]([C@@H]([C@H](O[C@H]1COC(=O)c1ccccc1)Oc1ccc(cc1)[N+](=O)[O-])O)OC(O2)(C)C
• Canonical SMILES: O[C@@H]1[C@H](O[C@H]([C@H]2[C@@H]1OC(O2)(C)C)COC(=O)c1ccccc1)Oc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C22H23NO9/c1-22(2)31-18-16(12-28-20(25)13-6-4-3-5-7-13)30-21(17(24)19(18)32-22)29-15-10-8-14(9-11-15)23(26)27/h3-11,16-19,21,24H,12H2,1-2H3/t16-,17-,18+,19-,21+/m1/s1
• InChIKey: CSHZQZHFVYLOSN-YRIDSSQKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3aS,4R,6R,7R,7aR)-7-hydroxy-2,2-dimethyl-6-(4-nitrophenoxy)-hexahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate
• IUPAC Traditional name: [(3aS,4R,6R,7R,7aR)-7-hydroxy-2,2-dimethyl-6-(4-nitrophenoxy)-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl benzoate
• Synonyms: p-Nitrophenyl 6-O-Benzoyl-3,4-O-isopropylidene-α-D-galactopyranoside

Database IDs

• PubChem SID: 164231231
• PubChem CID: 71751088

CALCULATED PROPERTIES

• Acid pKa: 12.342114
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 3.539321
• LogD (pH = 7.4): 3.5393162
• Log P: 3.539321
• Molar Refractivity: 109.537 cm^3
• Polarizability: 43.000084 Å^3
• Polar Surface Area: 129.27 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 104-107°C

REFERENCES

• Carbohyd. Res., 4, 189 (1967)
• Can. J. Chem., 59, 314 (1967)
• J. Carbohydrate Chem., 11(1967)
• 397 (1992)