isopropylidene-[G-2]-benzyl ester | 205878-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: isopropylidene-[G-2]-benzyl ester
• 英文别名: [2-Methyl-3-oxo-3-phenylmethoxy-2-[(2,2,5-trimethyl-1,3-dioxane-5-carbonyl)oxymethyl]propyl] 2,2,5-trimethyl-1,3-dioxane-5-carboxylate
• CAS: 205878-77-9
• 化学式: C₂₈H₄₀O₁₀
• 分子量: 536.62
• InChiKey: FLALLXRVKBRWKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  isopropylidene-[G-2]-benzyl ester 在 硫酸 作用下， 以 甲醇 、 水 为溶剂， 生成 isopropylidene-[G-2]-benzyl ester
  参考文献：
  名称：

  多价化对手性HPLC对映选择性分离介质性能的影响，该方法是通过脂肪族树枝状分子将多个选择剂连接到多孔聚合物载体上而制得的。

  摘要：

  已经使用两种不同方法制备了包含L-脯氨酸茚满苯胺内酯手性选择剂的手性固定相（CSP），该手性固定剂通过多价树状连接基连接到单分散的大孔聚（甲基丙烯酸2-羟乙基酯-二甲基丙烯酸乙烯酯-共-乙烯）珠上。收敛方法涉及溶液中配体的制备及其随后与载体的连接。发散方法基于使用固相合成的典型方法的接头的逐步“珠上”形成。尽管会聚的CSP具有明确定义的配体，但它们的负载相对较低。相反，发散技术为CSP提供了更高的负载量，但对精确配体结构的控制更为有限。

  DOI：

  10.1021/jo011005x
• 作为产物：
  描述：

  2,2-二羟甲基丙酸 在 1,4-二甲基吡啶鎓对甲苯磺酸盐 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 isopropylidene-[G-2]-benzyl ester
  参考文献：
  名称：

  通过在焦点处涉及手性区分的自组装方法构建 Janus 树枝状聚合物

  摘要：

  报道了一种通过异配型 Zn( II ) BOX 复合物的手性定向自组装构建 Janus 树枝状聚合物的策略。该方法允许原位定量合成 Janus 树枝状聚合物，无需纯化。Janus 树枝状聚合物的每个树枝状结构域都可以在焦点处拆卸后回收。

  DOI：

  10.1039/d1cc01973b

文献信息

• Designing Macromolecules for Therapeutic Applications:  Polyester DendrimerPoly(ethylene oxide) “Bow-Tie” Hybrids with Tunable Molecular Weight and Architecture
  作者：Elizabeth R. Gillies、Jean M. J. Fréchet

  DOI：10.1021/ja028100n

  日期：2002.11.1

  of the dendrons and the mass of the poly(ethylene oxide) chains, the molecular weight, architecture, and drug loading can be readily controlled. The "bow-tie" shaped dendritic scaffold was synthesized using both convergent and divergent methods, with orthogonal protecting groups on the periphery of the two dendrons. Poly(ethylene oxide) was then attached to the periphery of one dendron using an efficient

  描述了用于药物递送和相关治疗应用的新型聚酯树枝状聚合物、聚（环氧乙烷）杂化系统的设计和制备。这些系统由两个共价连接的聚酯树突组成，其中一个树突提供多种功能性手柄用于连接治疗活性部分，而另一个用于连接增溶聚（环氧乙烷）链。通过改变树枝的生成和聚（环氧乙烷）链的质量，可以很容易地控制分子量、结构和载药量。使用会聚和发散方法合成“领结”形树突支架，在两个树突的外围具有正交保护基团。然后使用有效的偶联程序将聚（环氧乙烷）连接到一个树突的外围。制备了一个包含 8 个分子量范围从约 20 kDa 到 160 kDa 的载体的小型文库，并通过各种技术对其进行了表征，证实了它们的明确结构。
• Self-assembled oligonucleotide-polyester dendrimers
  作者：Sarah L. Goh、Matthew B. Francis、Jean M. J. Fréchet

  DOI：10.1039/b209029e

  日期：——

  A new approach to the controlled synthesis of multicomponent dendrimers is presented, in which three oligonucleotide–dendron conjugates were synthesized using solid phase techniques and hybridized to create a second generation polyester dendrimer with DNA as a core and bearing two types of peripheral functional groups.

  提出了一种新方法，用于控制合成多组分树枝状聚合物，其中利用固相技术合成了三种寡核苷酸-树枝状体共轭物，并进行杂交以创建一种第二代聚酯树枝状聚合物，其核心为DNA，且具有两种类型的外围功能团。
• Effect of Multivalency on the Performance of Enantioselective Separation Media for Chiral HPLC Prepared by Linking Multiple Selectors to a Porous Polymer Support via Aliphatic Dendrons
  作者：Frank H. Ling、Victor Lu、Frantisek Svec、Jean M. J. Fréchet

  DOI：10.1021/jo011005x

  日期：2002.4.1

  multivalent dendritic linker to monodisperse macroporous poly(2-hydroxyethyl methacrylate-co-ethylene dimethacrylate) beads have been prepared using two different approaches. The convergent method involves the preparation of ligands in solution and their subsequent attachment to the support. The divergent approach is based on the stepwise "on-bead" formation of the linker using methods that are typical

  已经使用两种不同方法制备了包含L-脯氨酸茚满苯胺内酯手性选择剂的手性固定相（CSP），该手性固定剂通过多价树状连接基连接到单分散的大孔聚（甲基丙烯酸2-羟乙基酯-二甲基丙烯酸乙烯酯-共-乙烯）珠上。收敛方法涉及溶液中配体的制备及其随后与载体的连接。发散方法基于使用固相合成的典型方法的接头的逐步“珠上”形成。尽管会聚的CSP具有明确定义的配体，但它们的负载相对较低。相反，发散技术为CSP提供了更高的负载量，但对精确配体结构的控制更为有限。
• Welsh, Daniel J.; Jones, Simon P.; Smith, David K., Angewandte Chemie - International Edition, 2009, vol. 48, p. 4047 - 4051
  作者：Welsh, Daniel J.、Jones, Simon P.、Smith, David K.

  DOI：——

  日期：——
• Degradable Self-Assembling Dendrons for Gene Delivery: Experimental and Theoretical Insights into the Barriers to Cellular Uptake
  作者：Anna Barnard、Paola Posocco、Sabrina Pricl、Marcelo Calderon、Rainer Haag、Mark E. Hwang、Victor W. T. Shum、Daniel W. Pack、David K. Smith

  DOI：10.1021/ja2070736

  日期：2011.12.21

  This paper uses a combined experimental and theoretical approach to gain unique insight into gene delivery. We report the synthesis and investigation of a new family of second-generation dendrons with four triamine surface ligands capable of binding to DNA, degradable aliphatic-ester dendritic scaffolds, and hydrophobic units at their focal points. Dendron self-assembly significantly enhances DNA binding as monitored by a range of experimental methods and confirmed by multiscale modeling. Cellular uptake studies indicate that some of these dendrons are highly effective at transporting DNA into cells (ca. 10 times better than poly(ethyleneimine), PEI). However, levels of transgene expression are relatively low (ca. 10% of PEI). This indicates that these dendrons cannot navigate all of the intracellular barriers to gene delivery. The addition of chloroquine indicates that endosomal escape is not the limiting factor in this case, and it is shown, both experimentally and theoretically, that gene delivery can be correlated with the ability of the dendron assemblies to release DNA. Mass spectrometric assays demonstrate that the dendrons, as intended, do degrade under biologically relevant conditions over a period of hours. Multiscale modeling of degraded dendron structures suggests that complete dendron degradation would be required for DNA release. Importantly, in the presence of the lower pH associated with endosomes, or when bound to DNA, complete degradation of these dendrons becomes ineffective on the transfection time scale we propose this explains the poor transfection performance of these dendrons. As such, this paper demonstrates that taking this kind of multidisciplinary approach can yield a fundamental insight into the way in which dendrons can navigate barriers to cellular uptake. Lessons learned from this work will inform future dendron design for enhanced gene delivery.