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

• ChemBase ID: 162891
• Molecular Formular: C16H23BrO10
• Molecular Mass: 455.25182
• Monoisotopic Mass: 454.04745894
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)OCCBr)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: BrCCO[C@@H]1O[C@@H](COC(=O)C)[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C16H23BrO10/c1-8(18)23-7-12-13(24-9(2)19)14(25-10(3)20)15(26-11(4)21)16(27-12)22-6-5-17/h12-16H,5-7H2,1-4H3/t12-,13-,14+,15-,16-/m1/s1
• InChIKey: WAUIUUNDCFRMRS-IBEHDNSVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-(2-bromoethoxy)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-(2-bromoethoxy)oxan-2-yl]methyl acetate
• Synonyms: 2-Bromoethyl β-D-Glucopyranoside 2,3,4,6-Tetraacetate; 2'-Bromoethyl 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranoside

Database IDs

• CAS Number: 16977-78-9
• PubChem SID: 162257026
• PubChem CID: 10623633

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.32507405
• LogD (pH = 7.4): 0.32507405
• Log P: 0.32507405
• Molar Refractivity: 89.6074 cm^3
• Polarizability: 37.191975 Å^3
• Polar Surface Area: 123.66 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Ethanol; Ethyl Acetate; Methanol,
• Apperance: White Crystalline Solid
• Melting Point: 117°C

REFERENCES

• Reinhard, J., et al.: J. Med. Chem., 44, 4050 (2001)
• Guan, L., et al.: J. Biol. Chem., 278, 10641 (2001)