tert-butyl (2S)-2-[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-[(Z)-octadec-9-enoyl]oxy-2-[[2-[2-[2-[2-[2-[2-(2-phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetyl]oxymethyl]oxolan-3-yl]carbamoyl]pyrrolidine-1-carboxylate | 1415634-26-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: tert-butyl (2S)-2-[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-[(Z)-octadec-9-enoyl]oxy-2-[[2-[2-[2-[2-[2-[2-(2-phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetyl]oxymethyl]oxolan-3-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 1415634-26-2
• 化学式: C₅₈H₉₂N₄O₁₇
• 分子量: 1117.39
• InChiKey: HYIZPZZMCMNWGV-SLYMTFSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  79
• 可旋转键数：
  47
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  235
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-[(Z)-octadec-9-enoyl]oxy-2-[[2-[2-[2-[2-[2-[2-(2-phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetyl]oxymethyl]oxolan-3-yl]carbamoyl]pyrrolidine-1-carboxylate 在 氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(2R,3R,4S,5S)-2-(2,4-dioxopyrimidin-1-yl)-5-[[2-[2-[2-[2-[2-[2-(2-phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetyl]oxymethyl]-4-[[(2S)-pyrrolidine-2-carbonyl]amino]oxolan-3-yl] (Z)-octadec-9-enoate;hydrochloride
  参考文献：
  名称：

  Synthesis, self-aggregation and bioactivity properties of a cationic aminoacyl surfactant, based on a new class of highly functionalized nucleolipids

  摘要：

  A highly functionalized aminoacyl nucleolipid based on uridine is here proposed as a novel cationic surfactant. To achieve this, a straightforward, high yielding and versatile protocol has been devised, in principle providing synthetic access to a variety of different, related analogs. Self-aggregation properties of this nucleolipid were determined by using a combined approach, including surface tension, conductivity and DLS measurements. Above the critical micellar concentration of 4 x 10(-5) mol kg(-1), large supramolecular assemblies with a counterion condensation degree of 0.25 were observed. The bioactivity profile of this new compound was investigated on cancer and non cancer cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.044
• 作为产物：
  描述：

  [(2R,3R,4S,5S)-4-azido-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-(2,4-dioxopyrimidin-1-yl)oxolan-3-yl] (Z)-octadec-9-enoate 在 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氢气 、 triethylamine tris(hydrogen fluoride) 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 38.0h， 生成 tert-butyl (2S)-2-[[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-[(Z)-octadec-9-enoyl]oxy-2-[[2-[2-[2-[2-[2-[2-(2-phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetyl]oxymethyl]oxolan-3-yl]carbamoyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Synthesis, self-aggregation and bioactivity properties of a cationic aminoacyl surfactant, based on a new class of highly functionalized nucleolipids

  摘要：

  A highly functionalized aminoacyl nucleolipid based on uridine is here proposed as a novel cationic surfactant. To achieve this, a straightforward, high yielding and versatile protocol has been devised, in principle providing synthetic access to a variety of different, related analogs. Self-aggregation properties of this nucleolipid were determined by using a combined approach, including surface tension, conductivity and DLS measurements. Above the critical micellar concentration of 4 x 10(-5) mol kg(-1), large supramolecular assemblies with a counterion condensation degree of 0.25 were observed. The bioactivity profile of this new compound was investigated on cancer and non cancer cell lines. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.044