benzyl N-tris[(2-{[(tris{[2-(tert-butoxycarbonyl)ethoxy]methyl}methyl)amino]carbonyl}ethoxy)methyl]methylcarbamate | 404887-91-8

• 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: benzyl N-tris[(2-{[(tris{[2-(tert-butoxycarbonyl)ethoxy]methyl}methyl)amino]carbonyl}ethoxy)methyl]methylcarbamate
• 英文别名: Tert-butyl 3-[2-[3-[3-[3-[[1,3-bis[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]-2-[[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]methyl]propan-2-yl]amino]-3-oxopropoxy]-2-[[3-[[1,3-bis[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]-2-[[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]methyl]propan-2-yl]amino]-3-oxopropoxy]methyl]-2-(phenylmethoxycarbonylamino)propoxy]propanoylamino]-3-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]-2-[[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]methyl]propoxy]propanoate
• CAS: 404887-91-8
• 化学式: C₉₆H₁₆₄N₄O₃₅
• 分子量: 1934.36
• InChiKey: UYTGHSHBOXRAEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  135
• 可旋转键数：
  85
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  473
• 氢给体数：
  4
• 氢受体数：
  35

反应信息

• 作为反应物：
  描述：

  benzyl N-tris[(2-{[(tris{[2-(tert-butoxycarbonyl)ethoxy]methyl}methyl)amino]carbonyl}ethoxy)methyl]methylcarbamate 在 甲酸 作用下， 反应 18.0h， 以99%的产率得到benzyl N-{tris[(2-{[(tris{[2-carboxyethoxy]methyl}methyl)amino]carbonyl}ethoxy)methyl]methyl}carbamate
  参考文献：
  名称：

  Spatially Resolved Derivatization of Solid-Phase-Synthesis Beads with Fluorescent Dendrimers: Creation of Localized Microdomains

  摘要：

  Second and third generation Newkome-type trifurcated dendrimers, containing either a coumarin or dansyl fluorescent probe at the dendrimer core, have been synthesized and attached to ArgoGel (R) solid-phase-synthesis beads. Subsequent reaction with rhodamine dye shows that the dye can penetrate throughout the beads to acylate the remaining sites. Thus, it is possible to achieve a spatially resolved microdomain for library formation at the core of the dendrimer, primarily on the bead's periphery, and a second microdomain suitable for derivatization by other reagents such as encoding tags and fluorescent sensors.

  DOI：

  10.1002/1522-2675(200210)85:10<3532::aid-hlca3532>3.0.co;2-f
• 作为产物：
  描述：

  三[[2-(叔-丁氧羰基)乙氧基]甲基]甲胺 、 benzyl N-tris[(2-carboxyethyloxy)methyl]methylcarbamate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以50%的产率得到benzyl N-tris[(2-{[(tris{[2-(tert-butoxycarbonyl)ethoxy]methyl}methyl)amino]carbonyl}ethoxy)methyl]methylcarbamate
  参考文献：
  名称：

  合成碳水化合物受体中树突侧链的亲和力增强

  摘要：

  树突侧链已被用来修饰基于蒽的合成碳水化合物受体的结合环境。长度、电荷和支化的控制使得侧链羧酸酯基团的定位能够帮助结合底物而不是阻塞空腔。尽管系统具有灵活性，但树枝状聚合物的构象简并性导致了有效的预组织。观察到与水中的葡萄糖铵离子的强结合，K a 值高达7000  M -1。尽管存在溶剂竞争且不存在静电相互作用，但对不带电底物（葡萄糖和N-乙酰氨基葡萄糖）的亲和力也得到增强。

  DOI：

  10.1002/anie.201409124

文献信息

• An Improved Synthesis of a Trifurcated Newkome-Type Monomer and Orthogonally Protected Two-Generation Dendrons
  作者：Claudia M. Cardona、Robert E. Gawley

  DOI：10.1021/jo0161678

  日期：2002.2.1

  The one-step synthesis of amino-polyether tritert-butyl ester monomer 2, by condensation of TRIS with tert-butyl acrylate, is reported. The nitrogen of the monomer can be protected with a Cbz group; subsequent removal of the tert-butyl esters with formic acid affords a triacid that is coupled to three monomers to afford an orthogonally protected two-generation, trifurcated polyether-polyamide dendron. The Cbz protecting group may be removed from the second-generation dendron without disturbing the tertbutyl esters of the periphery.
• Self-Association of Protected Newkome-Type Second-Generation Dendrimers at Nanomolar Level Concentrations in Aqueous Solution
  作者：Subhendu K. Mohanty、Shyamala Thirunavukarasu、Sundarababu Baskaran、Ashok K. Mishra

  DOI：10.1021/ma0498215

  日期：2004.7.1

  Protected Newkome-type second-generation dendrimers (based on Lin's amine) were synthesized with a pyrene moiety attached to the core. The photophysical property in aqueous solution of the protected dendrimers shows self-association behavior in water. Pyrene excimer emission at 475 nm is observed in water even at very low concentrations of protected dendrimer (ca. 5 x 10(-8) M). This emission band is absent in other solvents even up to a concentration of 10(-5) M. The corresponding unprotected dendrimer does not show the pyrene excimer fluorescence. The amide of pyrene butyric acid with tert-butylamine shows the formation of excimer, albeit with very low intensity. Quenching studies on the dendrimer with hydrophilic quencher iodide anion (I-) reveal that there is significant quenching of fluorescence intensity in the case of N-tert-butyl-4-pyren-1-ylbutyramide as compared to that of the pyrene-attached second-generation protected dendrimer. This shows that the pyrene moiety in the case of the protected dendrimer is significantly shielded from the surrounding.
• Spatially Resolved Derivatization of Solid-Phase-Synthesis Beads with Fluorescent Dendrimers: Creation of Localized Microdomains
  作者：Claudia M. Cardona、Stephan H. Jannach、Hao Huang、Yukiko Itojima、Roger M. Leblanc、Robert E. Gawley、Gary A. Baker、Eric B. Brauns

  DOI：10.1002/1522-2675(200210)85:10<3532::aid-hlca3532>3.0.co;2-f

  日期：2002.10

  Second and third generation Newkome-type trifurcated dendrimers, containing either a coumarin or dansyl fluorescent probe at the dendrimer core, have been synthesized and attached to ArgoGel (R) solid-phase-synthesis beads. Subsequent reaction with rhodamine dye shows that the dye can penetrate throughout the beads to acylate the remaining sites. Thus, it is possible to achieve a spatially resolved microdomain for library formation at the core of the dendrimer, primarily on the bead's periphery, and a second microdomain suitable for derivatization by other reagents such as encoding tags and fluorescent sensors.
• Affinity Enhancement by Dendritic Side Chains in Synthetic Carbohydrate Receptors
  作者：Harry Destecroix、Charles M. Renney、Tiddo J. Mooibroek、Tom S. Carter、Patrick F. N. Stewart、Matthew P. Crump、Anthony P. Davis

  DOI：10.1002/anie.201409124

  日期：2015.2.9

  Dendritic side chains have been used to modify the binding environment in anthracene‐based synthetic carbohydrate receptors. Control of length, charge, and branching enabled the positioning of side‐chain carboxylate groups in such a way that they assisted in binding substrates rather than blocking the cavity. Conformational degeneracy in the dendrimers resulted in effective preorganization despite

  树突侧链已被用来修饰基于蒽的合成碳水化合物受体的结合环境。长度、电荷和支化的控制使得侧链羧酸酯基团的定位能够帮助结合底物而不是阻塞空腔。尽管系统具有灵活性，但树枝状聚合物的构象简并性导致了有效的预组织。观察到与水中的葡萄糖铵离子的强结合，K a 值高达7000  M -1。尽管存在溶剂竞争且不存在静电相互作用，但对不带电底物（葡萄糖和N-乙酰氨基葡萄糖）的亲和力也得到增强。
• High-Affinity Multivalent DNA Binding by Using Low-Molecular-Weight Dendrons
  作者：Mauri A. Kostiainen、John G. Hardy、David K. Smith

  DOI：10.1002/anie.200500066

  日期：2005.4.22