3,6,9,12,15,18,21-heptaoxatricosane-1,23-dioic acid di-tert-butyl ester | 211746-80-4

• 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: 3,6,9,12,15,18,21-heptaoxatricosane-1,23-dioic acid di-tert-butyl ester
• 英文别名: Tert-butyl 2-[2-[2-[2-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetate
• CAS: 211746-80-4
• 化学式: C₂₄H₄₆O₁₁
• 分子量: 510.623
• InChiKey: FDJPHLHMADKSBM-UHFFFAOYSA-N

物化性质

• 沸点：
  533.1±45.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  35
• 可旋转键数：
  26
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,6,9,12,15,18,21-heptaoxatricosane-1,23-dioic acid di-tert-butyl ester 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 七氧杂二十三烷二酸二(N-羟基琥珀酰亚胺)酯
  参考文献：
  名称：

  Ligand Recognition by E- and P-Selectin:  Chemoenzymatic Synthesis and Inhibitory Activity of Bivalent Sialyl Lewis x Derivatives and Sialyl Lewis x Carboxylic Acids

  摘要：

  Described is the preparation of five sLe(x) dimers and five sLe(x) carboxylic acids by coupling chemoenzymatically synthesized amino-substituted sialyl Lewis x (sLe(x)) derivative 4 to homobifunctional cross-linkers 20-24 of varying chain length. 20-24 were obtained by alkylating low-molecular-weight oligoethylene glycols with tert-butyl bromoacetate and subsequent transformation of the di-tert-butyl esters into disuccinimide esters. The products were assayed for inhibition against binding of a sLe(a)-polymer to immobilized E- and P-selectin. In the E-selectin assay all dimers had lower IC50 values than the sLex monomer. The results show that comparable binding enhancements can be obtained with linkers of completely different length and rigidity. In the P-selectin assay four of the five sLe(x) carboxylic acids displayed significantly improved inhibitory potency. The lowest IC50 value was observed for the compound with the shortest spacer between the sLex moiety and the additional carboxylate, being ca. 20-40 times more potent than unmodified sLex. These findings should be of importance for the design of new multivalent forms of sLe(x) as well as sLe(x) mimetics as high-affinity selectin ligands.

  DOI：

  10.1021/jo980350s
• 作为产物：
  描述：

  六甘醇 、 溴乙酸叔丁酯 在 氢氧化钾 、 四丁基硫酸氢铵 作用下， 以 甲苯 为溶剂， 以74%的产率得到3,6,9,12,15,18,21-heptaoxatricosane-1,23-dioic acid di-tert-butyl ester
  参考文献：
  名称：

  Ligand Recognition by E- and P-Selectin:  Chemoenzymatic Synthesis and Inhibitory Activity of Bivalent Sialyl Lewis x Derivatives and Sialyl Lewis x Carboxylic Acids

  摘要：

  Described is the preparation of five sLe(x) dimers and five sLe(x) carboxylic acids by coupling chemoenzymatically synthesized amino-substituted sialyl Lewis x (sLe(x)) derivative 4 to homobifunctional cross-linkers 20-24 of varying chain length. 20-24 were obtained by alkylating low-molecular-weight oligoethylene glycols with tert-butyl bromoacetate and subsequent transformation of the di-tert-butyl esters into disuccinimide esters. The products were assayed for inhibition against binding of a sLe(a)-polymer to immobilized E- and P-selectin. In the E-selectin assay all dimers had lower IC50 values than the sLex monomer. The results show that comparable binding enhancements can be obtained with linkers of completely different length and rigidity. In the P-selectin assay four of the five sLe(x) carboxylic acids displayed significantly improved inhibitory potency. The lowest IC50 value was observed for the compound with the shortest spacer between the sLex moiety and the additional carboxylate, being ca. 20-40 times more potent than unmodified sLex. These findings should be of importance for the design of new multivalent forms of sLe(x) as well as sLe(x) mimetics as high-affinity selectin ligands.

  DOI：

  10.1021/jo980350s

文献信息

• Multimeric Cyclic RGD Peptides as Potential Tools for Tumor Targeting: Solid-Phase Peptide Synthesis and Chemoselective Oxime Ligation
  作者：Georgette Thumshirn、Ulrich Hersel、Simon L. Goodman、Horst Kessler

  DOI：10.1002/chem.200204304

  日期：2003.6.16

  angiogenesis. Targeting this receptor may provide information about the receptor status of the tumor and enable specific therapeutic planning. Solid-phase peptide synthesis of multimeric cyclo(-RGDfE-)-peptides is described, which offer the possibility of enhanced integrin targeting due to polyvalency effects. These peptides contain an aminooxy group for versatile chemoselective oxime ligation. Conjugation

  alpha v beta 3整合素受体在人类转移和肿瘤诱导的血管生成中起重要作用。靶向该受体可以提供有关肿瘤的受体状态的信息，并可以进行特定的治疗计划。描述了多聚环（-RGDfE-）-肽的固相肽合成，由于多价效应，其提供了增强整联蛋白靶向性的可能性。这些肽含有一个氨基氧基，可进行通用的化学选择性肟连接。与对三甲基锡烷基苯甲醛结合产生放射性碘十二烷甲酰化的前体，这将使它们可用作靶向和成像表达αv beta 3的肿瘤细胞的潜在工具。不需要保护策略并且在温和条件下以高收率获得了缀合物。
• Ligand Recognition by E- and P-Selectin:  Chemoenzymatic Synthesis and Inhibitory Activity of Bivalent Sialyl Lewis x Derivatives and Sialyl Lewis x Carboxylic Acids
  作者：Valentin Wittmann、Shuichi Takayama、Ke Wei Gong、Gabriele Weitz-Schmidt、Chi-Huey Wong

  DOI：10.1021/jo980350s

  日期：1998.7.1

  Described is the preparation of five sLe(x) dimers and five sLe(x) carboxylic acids by coupling chemoenzymatically synthesized amino-substituted sialyl Lewis x (sLe(x)) derivative 4 to homobifunctional cross-linkers 20-24 of varying chain length. 20-24 were obtained by alkylating low-molecular-weight oligoethylene glycols with tert-butyl bromoacetate and subsequent transformation of the di-tert-butyl esters into disuccinimide esters. The products were assayed for inhibition against binding of a sLe(a)-polymer to immobilized E- and P-selectin. In the E-selectin assay all dimers had lower IC50 values than the sLex monomer. The results show that comparable binding enhancements can be obtained with linkers of completely different length and rigidity. In the P-selectin assay four of the five sLe(x) carboxylic acids displayed significantly improved inhibitory potency. The lowest IC50 value was observed for the compound with the shortest spacer between the sLex moiety and the additional carboxylate, being ca. 20-40 times more potent than unmodified sLex. These findings should be of importance for the design of new multivalent forms of sLe(x) as well as sLe(x) mimetics as high-affinity selectin ligands.