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

• ChemBase编号: 158926
• 分子式: C14H20FNO8
• 平均质量: 349.3089032
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: [(2R,3S,4R,5R)-4,6-bis(acetyloxy)-5-acetamido-3-fluorooxan-2-yl]methyl acetate
• IUPAC传统名: [(2R,3S,4R,5R)-4,6-bis(acetyloxy)-5-acetamido-3-fluorooxan-2-yl]methyl acetate
• 别名: 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

登记号

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

理论计算性质

• Acid pKa: 11.776765
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): -1.0061069
• LogD (pH = 7.4): -1.0061226
• Log P: -1.0061064
• 摩尔折射率: 72.7871 cm^3
• 极化性: 30.120184 Å^3
• 极化表面积: 117.23 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Acetone; Chloroform; Dichloromethane
• 外观: White Solid

安全信息

• 保存条件: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

详细说明

Toronto Research Chemicals - A158435

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

参考文献

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