tert-butyl N-{[({tris[(2-carboxyethoxy)methyl]methyl}amino)carbonyl]methyl}carbamate | 247941-85-1

• 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: tert-butyl N-{[({tris[(2-carboxyethoxy)methyl]methyl}amino)carbonyl]methyl}carbamate
• 英文别名: N-(tert-butoxycarbonylglycinyl)tris(carboxyethoxymethyl)aminomethane；BocNH-acetylamino-tris tri-acid；3-[3-(2-carboxyethoxy)-2-(2-carboxyethoxymethyl)-2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]propoxy]propanoic acid
• CAS: 247941-85-1
• 化学式: C₂₀H₃₄N₂O₁₂
• 分子量: 494.496
• InChiKey: QTDCKRTWJUTSGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  34
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  207
• 氢给体数：
  5
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-[2-(2-Amino-acetylamino)-3-(2-ethoxycarbonyl-ethoxy)-2-(2-ethoxycarbonyl-ethoxymethyl)-propoxy]-propionic acid ethyl ester 、 tert-butyl N-{[({tris[(2-carboxyethoxy)methyl]methyl}amino)carbonyl]methyl}carbamate 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Dendritic Tryptophan Derivatives and Investigation on Dendritic Effects of their Fluorescence and Reactivity

  摘要：

  两系列树枝状色氨酸衍生物已被合成和表征，研究并比较了它们在不同溶剂中的发射光谱以及色氨酸的反应性。随着树枝状壳层的大小或代数增加，色氨酸在发射波长中的屏蔽效应逐渐增强。

  DOI：

  10.2174/157017811796505007
• 作为产物：
  描述：

  tris(cyanoethoxymethyl)aminomethane 在 硫酸 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 tert-butyl N-{[({tris[(2-carboxyethoxy)methyl]methyl}amino)carbonyl]methyl}carbamate
  参考文献：
  名称：

  Synthesis of Dendritic Tryptophan Derivatives and Investigation on Dendritic Effects of their Fluorescence and Reactivity

  摘要：

  两系列树枝状色氨酸衍生物已被合成和表征，研究并比较了它们在不同溶剂中的发射光谱以及色氨酸的反应性。随着树枝状壳层的大小或代数增加，色氨酸在发射波长中的屏蔽效应逐渐增强。

  DOI：

  10.2174/157017811796505007

文献信息

• Catalytic Dendrophanes as Enzyme Mimics: Synthesis, Binding Properties, Micropolarity Effect, and Catalytic Activity of Dendritic Thiazolio-cyclophanes
  作者：Tilo Habicher、François Diederich、Volker Gramlich

  DOI：10.1002/(sici)1522-2675(19990707)82:7<1066::aid-hlca1066>3.0.co;2-o

  日期：1999.7.7

  Catalytic dendrophanes 9 and 10 were prepared as functional mimics of the thiamine-diphosphate-dependent enzyme pyruvate oxidase, and studied as catalysts in the oxidation of naphthalene-2-carbaldehyde (4) to methyl naphthalene-2-carboxylate (8) (Scheme 1). They are composed of a thiazolio-cyclophane initiator core with four generation-2 (G-2) poly(etheramide) dendrons attached. The two dendrophanes were synthesized by a convergent growth strategy by coupling dendrons 11 and 12, respectively (Scheme 2), with (chloromethyl)-cyclophane 42 (Scheme 5) and subsequent conversion with 4-methylthiaaole (Scheme 7). The X-ray crystal structures of cyclophane precursors 30 (Scheme 3), 37 and 38 (Scheme 5) on the way to dendrophanes were determined (Fig. I). The crystal-structure analysis of the benzene clathrate of 37 revealed the formation of channel-like stacks by the cyclophane which incorporate its morpholinomethyl side chain and the enclathrated benzene molecule (Fig. 2). The interactions of the enclathrated benzene molecule with the phenyl rings of the two adjacent cyclophane molecules in the stack closely resemble those between neighboring benzene molecules in crystalline benzene (Fig. 3). The characterization by MALDI-TOF-MS (Fig. 4) and H-1- and C-13-NMR spectroscopy (Fig. 5) proved the monodispersity of the G-2 dendrophanes 9 and 10 with molecular weights up to 11500 Da (Eor 10). H-1-NMR and fluorescence binding titrations in H2O and aqueous MeOH showed that 9 and 10 form stable 1:1 complexes with naphthalene-2-carbaldehyde (4) and 6-(p-toluidino)naphthalene-2-sulfonate (48, TNS) (Tables 1 and 2). The evaluation of the fluorescence-emission maxima of bound TNS revealed that the dendritic branching creates a microenvironment of distinctly reduced polarity at the cyclophane core by limiting its exposure to bulk solvent. Initial rate studies for the oxidation of naphthalene-2-carbaldehyde to methyl naphthalene-2-carboxylate in basic aqueous MeOH in the presence of flavin derivative 6 revealed only a weak catalytic activity of dendrophanes 9 and 10 (Table 3), despite the favorable micropolarity at the cyclophane active site. The low catalytic activity in the interior of the macromolecules was explained by steric hindrance of reaction transition states by the dendritic branches.
• Design and Synthesis of Novel <i>N</i>-Acetylgalactosamine-Terminated Glycolipids for Targeting of Lipoproteins to the Hepatic Asialoglycoprotein Receptor
  作者：Patrick C. N. Rensen、Steven H. van Leeuwen、Leo A. J. M. Sliedregt、Theo J. C. van Berkel、Erik A. L. Biessen

  DOI：10.1021/jm049481d

  日期：2004.11.1

  A novel glycolipid has been prepared that contains a cluster glycoside with an unusually high affinity for the asialoglycoprotein receptor (ASGPr) and a bile acid moiety that mediates stable incorporation into lipidic particles. The glycolipid spontaneously associated with low-density lipoproteins (LDL) and high-density lipoproteins (HDL) within human and murine plasma, and loading of lipoproteins with this glycolipid resulted in an efficient dose-dependent recognition and uptake of LDL and HDL by the liver (and not by spleen) upon intravenous injection into wild-type mice. Preinjection with asialoorosomucoid largely inhibited the uptake, establishing that both HDL and LDL were selectively recognized and processed by the ASGPr on liver parenchymal cells. Finally, repeated intravenous administration of the glycolipid to hyperlipidemic LDL receptor-deficient mice evoked an efficient and persistent cholesterol-lowering effect. These results indicate that the glycolipid may be a promising alternative for the treatment of hyperlipidemic patients who do not respond sufficiently to current cholesterol-lowering therapies.
• US9345781B2
  申请人：——

  公开号：US9345781B2

  公开（公告）日：2016-05-24
• Synthesis of Dendritic Tryptophan Derivatives and Investigation on Dendritic Effects of their Fluorescence and Reactivity
  作者：Dongsheng He、Gu He、Li Guo

  DOI：10.2174/157017811796505007

  日期：2011.9.1

  Two series of dendritic tryptophan derivatives have been synthesized and characterized, their emission spectra in different solvents and the reactivity of tryptophan were investigated and compared. There was a progressive shielding effect of the tryptophan in the emissive wavelengths of dendrimers increased with the size or generation of the dendritic shell.

  两系列树枝状色氨酸衍生物已被合成和表征，研究并比较了它们在不同溶剂中的发射光谱以及色氨酸的反应性。随着树枝状壳层的大小或代数增加，色氨酸在发射波长中的屏蔽效应逐渐增强。