tris(5-acetoxy-2-oxapentyl)-N-(tert-butyloxycarbonyl)methylamine | 1038802-16-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tris(5-acetoxy-2-oxapentyl)-N-(tert-butyloxycarbonyl)methylamine
• 英文别名: N-(BOC)-tris[(acetoxypropoxy)methyl]aminomethane
• CAS: 1038802-16-2
• 化学式: C₂₄H₄₃NO₁₁
• 分子量: 521.606
• InChiKey: BHASZAZYCQECFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  36.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  144.92
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  tris(5-acetoxy-2-oxapentyl)-N-(tert-butyloxycarbonyl)methylamine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 N-(BOC)-tris[(hydroxypropoxy)methyl]aminomethane
  参考文献：
  名称：

  Trivalent, Gal/GalNAc-containing ligands designed for the asialoglycoprotein receptor

  摘要：

  A series of novel, fluorescent ligands designed to bind with high affinity and specificity to the asialoglycoprotein receptor (ASGP-R) has been synthesized and tested on human liver cells. The compounds bear three non-reducing, beta-linked Gal or GalNAc moieties linked to flexible spacers for an optimal spatial interaction with the binding site of the ASGP-R. The final constructs were selectively endocytosed by HepG2 cells derived from parenchymal liver cells-the major human liver cell type-in a process that was visualized with the aid of fluorescence microscopy. Furthermore, the internalization was analyzed with flow cytometry, which showed the process to be receptor-mediated and selective. The compounds described in this work could serve as valuable tools for studying hepatic endocytosis, and are suited as carriers for site-specific drug delivery to the liver. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.017
• 作为产物：
  描述：

  N-(BOC)-tris[(hydroxypropoxy)methyl]aminomethane 、 乙酸酐 在 吡啶 作用下， 反应 3.0h， 以1.49 g的产率得到tris(5-acetoxy-2-oxapentyl)-N-(tert-butyloxycarbonyl)methylamine
  参考文献：
  名称：

  Trivalent, Gal/GalNAc-containing ligands designed for the asialoglycoprotein receptor

  摘要：

  A series of novel, fluorescent ligands designed to bind with high affinity and specificity to the asialoglycoprotein receptor (ASGP-R) has been synthesized and tested on human liver cells. The compounds bear three non-reducing, beta-linked Gal or GalNAc moieties linked to flexible spacers for an optimal spatial interaction with the binding site of the ASGP-R. The final constructs were selectively endocytosed by HepG2 cells derived from parenchymal liver cells-the major human liver cell type-in a process that was visualized with the aid of fluorescence microscopy. Furthermore, the internalization was analyzed with flow cytometry, which showed the process to be receptor-mediated and selective. The compounds described in this work could serve as valuable tools for studying hepatic endocytosis, and are suited as carriers for site-specific drug delivery to the liver. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.03.017

文献信息

• Adaptable Synthesis of <i>C</i>-Glycosidic Multivalent Carbohydrates and Succinamide-Linked Derivatization
  作者：Gavin J. Miller、John M. Gardiner

  DOI：10.1021/ol102310x

  日期：2010.11.19

  A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic D-mannose, D-glucose, and D-galactose derivatives with different length C1-linked spacer units and also core units with different length linker units attached. The central core scaffold is additionally functionalized via a succinamide-based, conjugatable linker unit, exemplified in an extended multivalent derivative [31] and a pyrene-bearing fluorsecent-labeled tris-C-mannosyl conjugate [33].