4-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside | 52571-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-(4-iodophenoxy)oxan-2-yl]methyl acetate
• CAS: 52571-61-6
• 化学式: C₂₀H₂₃IO₁₀
• 分子量: 550.301
• InChiKey: FWXMCVYOVAPZQT-CXQPBAHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 在 Amberlite 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 p-iodophenyl-α-D-galactopyranoside
  参考文献：
  名称：

  Blanc-Muesser, Michele; Driguez, Hugues, Journal of the Chemical Society. Perkin transactions I, 1988, p. 3345 - 3352

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2,3,4,6-D-葡萄糖五乙酸酯 在 ammonium cerium(IV) nitrate 、 四氯化锡 、 四丁基碘化铵 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 4-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
  参考文献：
  名称：

  Glycocinnasperimicin D 合成研究：从苯基糖苷开始，通过碘化-Heck 反应序列合成肉桂酰糖苷

  摘要：

  从苯基糖苷开始，通过碘化-Heck 反应序列开发了一种合成肉桂酰糖苷的新方法。该程序的成功应用完成了氨基糖类抗生素glucinnasperimicin D的正确核心结构的构建。

  DOI：

  10.1055/s-2003-43376

文献信息

• Synthesis of some oligopyridine–galactose conjugates and their metal complexes: a simple entry to multivalent sugar ligands
  作者：Simonetta Orlandi、Rita Annunziata、Maurizio Benaglia、Franco Cozzi、Leonardo Manzoni

  DOI：10.1016/j.tet.2005.08.018

  日期：2005.10

  Some galactose–oligopyridine conjugates were readily assembled by combining differently functionalized oligopyridines with peracetylated galactose derivatives. Variation in the structure of the components and of the linkers employed for their connection afforded adducts of different size, shape, and conformational mobility. Complexation of the bipyridine ligands with CuOTf and of the terpyridine ligand

  通过将不同功能化的低聚吡啶与过乙酰化的半乳糖衍生物结合起来，可以容易地组装一些半乳糖-低聚吡啶共轭物。组分和用于连接它们的接头的结构的变化提供了不同大小，形状和构象迁移率的加合物。联吡啶配体与CuOTf的络合和联吡啶配体与Zn（OTf）2的络合分别提供了相应的过乙酰化的2：1和1：1复合物，为单一物种。根据光谱证据，确定其结构为四面体（Cu络合物）和三角双锥体（Zn络合物）。从配体上除去乙酰保护基，得到相应的多元醇。与联吡啶-Cu（I）络合物不同，三联吡啶-Zn（II）络合物在除去乙酰基保护基团后仍保持其结构。
• Water soluble luminescent platinum terpyridine complexes with glycosylated acetylide and arylacetylide ligands: photoluminescent properties and cytotoxicities
  作者：Dik-Lung Ma、Tina Yuen-Ting Shum、Fuyi Zhang、Chi-Ming Che、Mengsu Yang

  DOI：10.1039/b507114c

  日期：——

  Platinum(II) terpyridine complexes with glycosylated acetylide and arylacetylide ligands bind to DNA with binding constants ∼105 mol−1 dm3; the glycosylated arylacetylide complexes exhibit emission at λmax ≈ 620 nm in water and are up to ∼100-times higher in potency than the clinical cisplatin drug in killing cancer cells.

  含糖基化乙炔和芳基乙炔配体的铂(II)三联吡啶配合物与DNA的结合常数约为10^5 mol−1 dm^3；糖基化芳基乙炔配合物在水中发射波长λmax约为620 nm，在杀死癌细胞方面，其效力比临床用药顺铂高出约100倍。
• A Europium Chelate for Quantitative Point-of-Care Immunoassays Using Direct Surface Measurement
  作者：Piia von Lode、Jaana Rosenberg、Kim Pettersson、Harri Takalo

  DOI：10.1021/ac0340051

  日期：2003.7.1

  New labels and assay techniques are needed to improve the sensitivity and quantitativeness of point-of-care immunotesting while sustaining the rapidity and ease of use of the assays. We synthesized a novel, intrinsically fluorescent nonadentate europium chelate with two chromophores and hydrophilic α-galactose side groups. The chelate is highly fluorescent, soluble in water, and provides effective shielding of Eu from water. The performance of the nonadentate chelate was compared with a heptadentate chelate in a dry reagent immunoassay for human chorionic gonadotropin (hCG). After 15-min incubation and washing, time-resolved fluorescence was measured directly from a wet or dried well surface. Contrary to the heptadentate label, the effect of aqueous quenching on the nonadentate label was found to be insignificant, with calculated analytical detection limits (background + 3 SD) of 0.9 and 0.7 IU/L hCG for wet and dry measurements, respectively, and a linear range up to 5000 IU/L. The CVs for the new label were <8% at the cutoff of 25 IU/L and above in both whole blood and plasma. The novel nonadentate label facilitates short turnaround times and simple instrumentation due to the absence of all signal development steps, at the same time retaining an excellent immunoassay performance.

  需要新的标签和检测技术来提高现场免疫检测的灵敏度和定量性，同时保持检测的快速性和易用性。我们合成了一种新型的内源性荧光非九齿铕配合物，具有两个色基和亲水性的α-半乳糖侧基。该配合物具有高度荧光性，易溶于水，并有效地保护铕不受水的影响。在对人绒毛膜促性腺激素（hCG）的干试剂免疫检测中，将非九齿配合物的性能与七齿配合物进行了比较。经过15分钟的孵育和洗涤后，从湿或干的孔表面直接测量了时间分辨荧光。与七齿标签相比，发现水相猝灭对非九齿标签的影响微乎其微，计算出的分析检测限（背景+3倍标准差）分别为湿测和干测的0.9和0.7 IU/L hCG，线性范围可达5000 IU/L。新标签在25 IU/L及以上的切割点处的变异系数（CV）均小于8%，适用于全血和血浆。该新型非九齿标签由于省略了所有信号开发步骤，促进了短周转时间和简单仪器的使用，同时保持了优异的免疫检测性能。
• BLANC-MUESSER, MICHELE;DRIGUEZ, HUGUES, J. CHEM. SOC. PERKIN TRANS. PT 1,(1988) N2, C. 3345-3351
  作者：BLANC-MUESSER, MICHELE、DRIGUEZ, HUGUES

  DOI：——

  日期：——