[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(2-chloro-4-nitrophenoxy)oxan-2-yl]methyl acetate

• ChemBase ID: 164483
• Molecular Formular: C20H22ClNO12
• Molecular Mass: 503.84118
• Monoisotopic Mass: 503.08305283
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)Oc1ccc(cc1Cl)[N+](=O)[O-])OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@@H]1O[C@@H](Oc2ccc(cc2Cl)[N+](=O)[O-])[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C20H22ClNO12/c1-9(23)29-8-16-17(30-10(2)24)18(31-11(3)25)19(32-12(4)26)20(34-16)33-15-6-5-13(22(27)28)7-14(15)21/h5-7,16-20H,8H2,1-4H3/t16-,17-,18+,19-,20-/m1/s1
• InChIKey: QRNIUQCWYQOPLO-OUUBHVDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(2-chloro-4-nitrophenoxy)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(2-chloro-4-nitrophenoxy)oxan-2-yl]methyl acetate
• Synonyms: 2-Chloro-4-nitrophenyl β-D-Glucopyranoside 2,3,4,6-Tetraacetate; 2-Chloro-4-nitrophenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Database IDs

• CAS Number: 35023-71-3
• PubChem SID: 162258618
• PubChem CID: 14559853

CALCULATED PROPERTIES

• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 1.7101429
• LogD (pH = 7.4): 1.7101429
• Log P: 1.7101429
• Molar Refractivity: 108.9188 cm^3
• Polarizability: 44.07057 Å^3
• Polar Surface Area: 169.48 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 144-145°C

REFERENCES

• Montgomery, E.M. et al.: JACS, 64, 690-694 (1942)