{2-[3-(2-tert-butoxycarbonylaminoethyl)thioureido]ethyl}carbamic acid tert-butyl ester | 209397-51-3

• 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: {2-[3-(2-tert-butoxycarbonylaminoethyl)thioureido]ethyl}carbamic acid tert-butyl ester
• 英文别名: 1,3-bis(2-((tert-butoxycarbonyl)amino)-ethyl)thiourea；6-Thioxo-2,5,7,10-tetraazaundecanedioic Acid 1,11-Bis(1,1-dimethylethyl) Ester；tert-butyl N-[2-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylcarbamothioylamino]ethyl]carbamate
• CAS: 209397-51-3
• 化学式: C₁₅H₃₀N₄O₄S
• 分子量: 362.494
• InChiKey: QAYIJAKXGIXKEW-UHFFFAOYSA-N

物化性质

• 密度：
  1.120±0.06 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  133
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {2-[3-(2-tert-butoxycarbonylaminoethyl)thioureido]ethyl}carbamic acid tert-butyl ester 在 氨 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 1,3-bis(2-(tert-butoxycarbonylamino)ethyl)-2-guanidinium iodide
  参考文献：
  名称：

  胍基“镊子”受体的固相合成

  摘要：

  适当官能化的胍已连接至固体支持物，从而允许肽链通过常规固相合成连接。这为具有羧酸根末端的肽的“镊子”受体文库的固相合成提供了基础。

  DOI：

  10.1016/0040-4039(96)01058-1
• 作为产物：
  描述：

  N-叔丁氧羰基-1,2-乙二胺 在 potassium carbonate 作用下， 以 乙醇 、 氯仿 、 水 为溶剂， 生成 {2-[3-(2-tert-butoxycarbonylaminoethyl)thioureido]ethyl}carbamic acid tert-butyl ester
  参考文献：
  名称：

  胍基“镊子”受体的固相合成

  摘要：

  适当官能化的胍已连接至固体支持物，从而允许肽链通过常规固相合成连接。这为具有羧酸根末端的肽的“镊子”受体文库的固相合成提供了基础。

  DOI：

  10.1016/0040-4039(96)01058-1

文献信息

• Trifluoroacetyl as an Orthogonal Protecting Group for Guanidines
  作者：Sandra Bartoli、Kim B. Jensen、Jeremy D. Kilburn

  DOI：10.1021/jo0348874

  日期：2003.11.1

  The trifluoroacetyl moiety has been used as a new protecting group for guanidine functionality. The protecting group is easily cleaved under mild basic conditions and is complementary to the Boc, Cbz, and Ddpe protecting groups. The protecting group can be applied to peptide synthesis in solution as well as on a solid phase as it is orthogonal to a Boc and Cbz strategy and semiorthogonal to an Fmoc

  三氟乙酰基部分已被用作胍官能团的新保护基。该保护基在温和的碱性条件下容易裂解，并且与Boc，Cbz和Ddpe保护基互补。该保护基可以在溶液中以及在固相上应用于肽合成，因为它与Boc和Cbz策略正交且与Fmoc策略半正交。
• Development of Novel Guanidine–Bisurea Bifunctional Organocatalysts and their Application to Asymmetric α-Hydroxylation of Tetralone-derived β-Keto Esters
  作者：Minami Odagi、Kan Takayama、Kota Furukori、Tatsuya Watanabe、Kazuo Nagasawa

  DOI：10.1071/ch14144

  日期：——

  A series of guanidine–bisurea bifunctional organocatalysts 4, with chiral centres located outside the urea groups, were synthesized. The novel catalyst 4 is conformationally more flexible than the original catalyst 1. In α-hydroxylation of tetralone- derived β-keto esters, 4 afforded the corresponding alcohols in high yields with moderate enantioselectivity.

  我们合成了一系列胍基-脲基双功能有机催化剂 4，其手性中心位于脲基之外。与原始催化剂 1 相比，新型催化剂 4 在构象上更为灵活。 在四氢酮衍生的 β-酮酯的α-羟基化反应中，4 能以中等对映选择性高产率生成相应的醇。
• Structure–Activity Examination of Poly(glycoamidoguanidine)s: Glycopolycations Containing Guanidine Units for Nucleic Acid Delivery
  作者：Vijay P. Taori、Hao Lu、Theresa M. Reineke

  DOI：10.1021/bm101537f

  日期：2011.6.13

  In this study we synthesized a new series of polymers known as poly(glycoamidoguanidine)s (PGAGs). These new polymer structures were synthesized by copolymerizing a carbohydrate monomer (diester; galatarate or tartarate) with a diamine incorporating guanidine or methylguanidine as a charge center to create a polyamide backbone. These materials were strategically designed and compared to our previously studied DNA delivery vehicles, poly(glycoamidoamine)s (PGAAs), which contain secondary amines as the charge groups along the polymer backbone to examine the effect of charge center type on the cellular delivery efficiency of plasmid DNA (pDNA). The guanidine moieties within the PGAGs facilitate electrostatic binding with the negatively charged phosphate backbone of plasmid DNA (pDNA). Stable polymer pDNA complexes (polyplexes) with sizes in the range of 60-200 nut are formed at polymer/pDNA charge ratios (NIP) of 5 and above. When the PGAGs are complexed with Cy5-labeled pDNA (Cy5-pDNA) at N/P ratios of 10 and 25, between 80 and 95% of HeLa cells were positive for Cy5 fluorescence, indicating effective cellular internalization of the polyplexes. The toxicity of both PGAA and PGAG polyplexes was studied via MTT assays, and over 95% cell survival was observed at N/P ratios of 5,10, 15, 20, 25, and 30 in HeLa cells. Transgene expression was examined via luciferase assays at various NIP ratios in the absence and presence of serum. In the absence of serum, the PGAG polyplexes revealed similar transgene expression when compared to polyplexes formed with their analogous PGAA structures. In the presence of serum, one analog (Gg) consisting of galactarate copolymerized with the guanidine monomer yielded gene expression similar to the positive control, Glycofect Transfection Reagent. This new series of guanidine-containing oligomers are promising as a new design strategy to incorporate an alternative charge center type within the backbone of glycopolymer-based nucleic acid delivery vehicles.
• The solid phase synthesis of a guanidinium based ‘tweezer’ receptor
  作者：Murielle Bonnat、Mark Bradley、Jeremy D. Kilburn

  DOI：10.1016/0040-4039(96)01058-1

  日期：1996.7

  An appropriately functionalised guanidine has been connected to a solid support, allowing peptide chains to be attached by conventional solid phase synthesis. This provides the basis for the solid-phase synthesis of libraries of ‘tweezer’ receptors for peptides with a carboxylate terminus.

  适当官能化的胍已连接至固体支持物，从而允许肽链通过常规固相合成连接。这为具有羧酸根末端的肽的“镊子”受体文库的固相合成提供了基础。