1-(2H-tetrahydropyran-2-yloxy)-17-tosyloxy-3,6,9,12,15-pentaoxaheptadecane | 669556-37-0

• 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: 1-(2H-tetrahydropyran-2-yloxy)-17-tosyloxy-3,6,9,12,15-pentaoxaheptadecane
• 英文别名: 17-(tetrahydro-2H-pyran-2-yloxy)-3,6,9,12,15-pentaoxaheptadecyl 4-methylbenzenesulfonate；1-p-toluenesulfonyloxy-17-(2H-tetrahydropyran-2'-yl)oxy-3,6,9,12,15-pentaoxaheptadecane；17-[(tetrahydro-2H-pyran-2-yl)oxy]-1-tosyloxy-3,6,9,12,15-pentaoxaheptadecane；THP-PEG7-Tos；2-[2-[2-[2-[2-[2-(oxan-2-yloxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
• CAS: 669556-37-0
• 化学式: C₂₄H₄₀O₁₀S
• 分子量: 520.642
• InChiKey: QGSBMQZFPAVLBB-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于DMSO、DCM、DMF

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  35
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

安全信息

• 储存条件：
  存储条件：2-8°C，需密封并置于干燥处。

制备方法与用途

THP-PEG8-Tos是一种PROTAC连接子，属于PEG类化合物，可用于合成PROTAC分子。

反应信息

• 作为反应物：
  描述：

  1-(2H-tetrahydropyran-2-yloxy)-17-tosyloxy-3,6,9,12,15-pentaoxaheptadecane 在 四丁基氢氧化铵 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 128.0h， 生成 1-(((5S)-2-((3,6,9,12,15,18-hexaoxaicosyl)oxy)-2-oxido-1,4,2-dioxaphosphinan-5-yl)methyl)-4-aminopyrimidin-2(1H)-one
  参考文献：
  名称：

  New prodrugs of Adefovir and Cidofovir

  摘要：

  New Adefovir (PMEA) prodrugs with a pro-moiety consisting of decyl or decyloxyethyl chain bearing hydroxyl function(s), hexaethyleneglycol or a (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl unit were prepared starting from the tetrabutylammonium salt of the phosphonate drug and an appropriate alkyl bromide or tosylate. Analogously, two esters of Cidofovir [(S)-HPMPC] bearing a hexaethyleneglycol moiety were prepared. The activity of the prodrugs was evaluated in vitro against different virus families. A loss in the antiviral activities of the hydroxylated decyl or decyloxyethyl esters and hexaethyleneglycol esters of PMEA against human immunodeficiency virus (HIV) and herpesviruses [ including herpes simplex virus (HSV), varicella-zoster virus (VZV), and human cytomegalovirus (CMV)] occurred in comparison with the parent compound. On the other hand, the (5-methyl-2-oxo-1,3-dioxolen-4-yl) methyl ester of PMEA showed significant activities against HIV and herpesviruses. (S)-HPMPC prodrugs exhibited anti-cytomegalovirus activities in the same range as the parent drug, whereas the anti-HSV and anti-VZV activities were one-to seven-fold lower than that of Cidofovir. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.016
• 作为产物：
  描述：

  六甘醇 在 4-甲基苯磺酸吡啶 、 potassium iodide 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.33h， 生成 1-(2H-tetrahydropyran-2-yloxy)-17-tosyloxy-3,6,9,12,15-pentaoxaheptadecane
  参考文献：
  名称：

  TUNABLE PHENYLACETYLENE HOSTS

  摘要：

  具有以下式的化合物或其盐：其中Y isn为1或2；每个R独立地为H、烷基、取代烷基、聚醚基、羧基、取代羧基、氨基甲酸酯、取代碳酸酯、羰酰氧基、烷氧基、取代烷氧基、卤代烷基、卤素、硝基、氨基、芳基氧基、氰基、羟基或磺酰基；R1为H、较低烷基或芳基烷基；R2从H、酰基、芳基烷基、磷酰基、—SO2R3；—C(O)R5；—C(O)OR7或—C(O)NR9R10中选择；R3；R5；R7；R9和R10独立地从H、较低烷基、芳基烷基或芳基中选择；R20从烷基、取代烷基、聚醚基、羧基、取代羧基、氨基甲酸酯、取代碳酸酯、羰酰氧基、烷氧基、取代烷氧基、卤代烷基、卤素、硝基、氨基、芳基氧基、氰基、羟基或磺酰基中选择。

  公开号：

  US20140031559A1

文献信息

• Ready-to-Use Germanium Surfaces for the Development of FTIR-Based Biosensors for Proteins
  作者：Pascale Blond、Robin Bevernaegie、Ludovic Troian-Gautier、Corinne Lagrost、Julie Hubert、François Reniers、Vincent Raussens、Ivan Jabin

  DOI：10.1021/acs.langmuir.0c02681

  日期：2020.10.13

  ready-to-use surfaces for biosensing applications. The grafted calixarene monolayer prevents nonspecific adsorption of proteins while allowing bioconjugation with biomolecules such as bovine serum albumin (BSA) or biotin. It is shown that the native form of the investigated proteins was maintained upon immobilization. As a proof of concept, the resulting calix[4]arene-based germanium biosensors were used

  锗特别适用于基于FTIR的蛋白质生物传感器的设计。然而，在锗表面上接枝稳定且薄的有机层仍然很困难。为了解决这个问题，我们开发了一种杯状[4]芳烃-四重氮盐，饰有四个寡聚（乙二醇）链和一个末端反应性羧基。这种通用的分子平台被共价接枝到锗表面上，从而产生了坚固耐用的即用型表面，可用于生物传感应用。接枝的杯芳烃单层防止蛋白质的非特异性吸附，同时允许与生物分子（例如牛血清白蛋白（BSA）或生物素）进行生物偶联。结果表明，所研究蛋白质的天然形式在固定后得以保持。作为概念证明，通过ATR-FTIR光谱学和荧光显微镜相结合，将得到的基于杯[4]芳烃的锗生物传感器用于从复杂培养基中选择性检测链霉亲和素。这项研究为开发专门用于蛋白质检测的灵敏且基于FTIR的生物传感器的开发提供了真正的可能性。
• Supramolecular formation of fibrous nanostructure in donor–acceptor dyad film
  作者：Takeshi Nishizawa、Keisuke Tajima、Kazuhito Hashimoto

  DOI：10.1039/b701438d

  日期：——

  A novel oligothiophene and its fullerene derivative were synthesized and their film morphologies were investigated. AFM images revealed that the oligothiophene formed well-aligned fiber-like nanostructures in the film after being thermally annealed at its liquid-crystalline temperature. In the oligothiophene–fullerene dyad film, fibers were already formed in the as-cast film. Thermal annealing further enhanced the structural order and a long, partially aligned fibrous nanostructure with a width of around 10 nm and a length of as long as 200 nm was observed. Combined with the results of X-ray analysis, these features were ascribed to supramolecular self-assembly via π–π interaction of the oligothiophene groups. Photovoltaic properties of the molecules were also investigated.

  一种新型寡聚噻吩及其富勒烯衍生物被合成，并对其薄膜形态进行了研究。原子力显微镜（AFM）图像显示，寡聚噻吩在其液晶温度下经过热退火后形成了良好排列的纤维状纳米结构。在寡聚噻吩-富勒烯二元薄膜中，已在铸膜状态下形成了纤维。热退火进一步增强了结构的有序性，观察到一种宽度约为10纳米、长度可达200纳米的长且部分对齐的纤维状纳米结构。结合X射线分析的结果，这些特征被归因于通过寡聚噻吩基团的π-π相互作用实现的超分子自组装。同时也对这些分子的光电性能进行了研究。
• Tunable phenylacetylene hosts
  申请人：State of Oregon, acting by and through the State Board of Higher Education on behalf of University of Oregon

  公开号：US08841460B2

  公开（公告）日：2014-09-23

  A compound, or a salt thereof, having the formula wherein Y is n is 1 or 2; each R is independently H, alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, aryloxy, cyano, hydroxyl, or sulfonyl; R1 is H, lower alkyl or aralkyl; R2 is selected from H, acyl, aralkyl, phosphonyl, —SO2R3; —C(O)R5; —C(O)OR7 or —C(O)NR9R10; R3; R5; R7; R9 and R10 independently are selected from H, lower alkyl, aralkyl or aryl; and R20 is selected from alkyl, substituted alkyl, a polyether moiety, carboxyl, substituted carboxyl, carbamate, substituted carbonate, carbonyloxy, alkoxy, substituted alkoxy, haloalkyl, halogen, nitro, amino, aryloxy, cyano, hydroxyl, or sulfonyl.

  具有下列式的化合物或其盐： 其中，Y为1或2；每个R独立地为H、烷基、取代烷基、聚醚基、羧基、取代羧基、氨基甲酸酯、取代碳酸酯、羰氧基、烷氧基、取代烷氧基、卤代烷基、卤素、硝基、氨基、芳氧基、氰基、羟基或磺酰基；R1为H、低烷基或芳基烷基；R2选择自H、酰基、芳基烷基、膦酸酯、-SO2R3、-C(O)R5、-C(O)OR7或-C(O)NR9R10；R3、R5、R7、R9和R10各自独立地选择自H、低烷基、芳基烷基或芳基；R20选择自烷基、取代烷基、聚醚基、羧基、取代羧基、氨基甲酸酯、取代碳酸酯、羰氧基、烷氧基、取代烷氧基、卤代烷基、卤素、硝基、氨基、芳氧基、氰基、羟基或磺酰基。
• Multigram Synthesis of Well-Defined Extended Bifunctional Polyethylene Glycol (PEG) Chains
  作者：François A. Loiseau、King Kuok (Mimi) Hii、Alison M. Hill

  DOI：10.1021/jo035042v

  日期：2004.2.1

  A series of novel, well-defined, unsymmetrical poly(ethylene glycol) chains of the type X(OCH2CH2)(n)Y (where X = protecting group; Y = nucleofuge or a different protecting group; n = 3, 6, 9, 12, 15, 18, and 24) were prepared in high yields by applying orthogonal protecting groups. The purity of the compounds was fully verified by elemental and high-resolution mass spectrometry analyses.
• A Chemoselective Approach to Grafting Biodegradable Polyesters
  作者：Ikuo Taniguchi、Anne M. Mayes、Eugene W. L. Chan、Linda G. Griffith

  DOI：10.1021/ma0487554

  日期：2005.1.1