(2S,3R,4R,5S,6S)-4,5-bis(acetyloxy)-6-bromo-2-methyloxan-3-yl acetate

• ChemBase ID: 158965
• Molecular Formular: C12H17BrO7
• Molecular Mass: 353.16318
• Monoisotopic Mass: 352.01576488
• SMILES: [C@@H]1([C@H]([C@@H]([C@@H]([C@@H](O1)Br)OC(=O)C)OC(=O)C)OC(=O)C)C
• Canonical SMILES: CC(=O)O[C@H]1[C@H](OC(=O)C)[C@H](C)O[C@H]([C@H]1OC(=O)C)Br
• InChI: InChI=1S/C12H17BrO7/c1-5-9(18-6(2)14)10(19-7(3)15)11(12(13)17-5)20-8(4)16/h5,9-12H,1-4H3/t5-,9+,10+,11-,12+/m0/s1
• InChIKey: XUZQAPSYNYIKSR-BSOOIWJMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,5S,6S)-4,5-bis(acetyloxy)-6-bromo-2-methyloxan-3-yl acetate
• IUPAC Traditional name: (2S,3R,4R,5S,6S)-4,5-bis(acetyloxy)-6-bromo-2-methyloxan-3-yl acetate
• Synonyms: 2,3,4-Tri-O-acetyl-α-L-fucopyranosyl Bromide; 6-Deoxy-α-L-galactopyranosyl Bromide 2,3,4-Triacetate; 2,3,4-Tri-O-acetyl-6-deoxy-α-L-galactopyranosyl Bromide; Acetobromofucose

Database IDs

• CAS Number: 16741-27-8
• PubChem SID: 162253100
• PubChem CID: 11473643

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.24044533
• LogD (pH = 7.4): 0.24044533
• Log P: 0.24044533
• Molar Refractivity: 68.1884 cm^3
• Polarizability: 28.265905 Å^3
• Polar Surface Area: 88.13 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: White Solid

REFERENCES

• Chen, L., et al.: Bioorg. Med. Chem., 14, 8295 (2006)
• Valdez, C., et al.: J. Med. Chem., 51, 3961 (2006)