[(2R,3S,4R,5R)-4,6-bis(acetyloxy)-5-acetamido-3-fluorooxan-2-yl]methyl acetate

• ChemBase ID: 158926
• Molecular Formular: C14H20FNO8
• Molecular Mass: 349.3089032
• Monoisotopic Mass: 349.11729483
• SMILES: [C@@H]1([C@@H]([C@@H](C(O[C@H]1COC(=O)C)OC(=O)C)NC(=O)C)OC(=O)C)F
• Canonical SMILES: CC(=O)OC[C@@H]1OC(OC(=O)C)[C@H]([C@H]([C@@H]1F)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C14H20FNO8/c1-6(17)16-12-13(22-8(3)19)11(15)10(5-21-7(2)18)24-14(12)23-9(4)20/h10-14H,5H2,1-4H3,(H,16,17)/t10-,11-,12-,13+,14?/m1/s1
• InChIKey: AUCRVLBGFFSCPW-LSGALXMHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R)-4,6-bis(acetyloxy)-5-acetamido-3-fluorooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R)-4,6-bis(acetyloxy)-5-acetamido-3-fluorooxan-2-yl]methyl acetate
• Synonyms: 2-(Acetylamino)-2,4-dideoxy-4-fluoro-D-glucopyranose 1,3,6-Triacetate; 2-Acetamido-4-fluoro-1,3,6-tri-O-acetyl-2,4-dideoxy-D-glucopyranose

Database IDs

• CAS Number: 116049-57-1
• PubChem SID: 162253061
• PubChem CID: 9819740

CALCULATED PROPERTIES

• Acid pKa: 11.776765
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -1.0061069
• LogD (pH = 7.4): -1.0061226
• Log P: -1.0061064
• Molar Refractivity: 72.7871 cm^3
• Polarizability: 30.120184 Å^3
• Polar Surface Area: 117.23 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane
• Apperance: White Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A158435

N-Acetylglucosamine analog, potent inhibitor P-selectin ligand activity

REFERENCES

• Dimitroff, C., et al.: J. Clin. Invest., 112, 1008 (2003)
• Descheny, L., et al.: J. Invest. Dermatol., 126, 2065 (2003)