tert-butyl 2-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxyacetate | 156703-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: tert-butyl 2-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxyacetate
• CAS: 156703-91-2
• 化学式: C₃₆H₄₀N₂O₁₀
• 分子量: 660.721
• InChiKey: NXTCWDQJGGXVBI-LXSYHGDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  48.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  147.54
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxyacetate 在 咪唑 、 四氮唑 、 氢氧化钾 、 N-羟基丁二酰亚胺 、 四丁基氟化铵 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 氨苯砜 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.5h， 生成
  参考文献：
  名称：

  Chemical Synthesis and Properties of Conformationally Fixed Diuridine Monophosphates as Building Blocks of the RNA Turn Motif

  摘要：

  Two intramolecularly cyclized diuridine monophosphates having an amide and a carbamate linker have been synthesized for fixation of the LT-turn structure found in various tRNAs and hammerhead ribozymes. The structural analysis of these cyclic dimers using CD, H-1 NMR, and P-31 NMR spectroscopy shows that they have ri,sid, unstacked conformations. Detailed computer simulations of their 3D structures based on molecular mechanics calculations suggest that a two-state equilibrium between a stretch and a turn conformation exists in favor of the former. The simulation also suggested that the diuridine mono-phosphate containing the carbamate-linker is better as a mimic of the U-turn structure than the amide-linked dimer. The enzymatic properties of these cyclized dimers are also described.

  DOI：

  10.1021/jo971797o
• 作为产物：
  描述：

  溴乙酸叔丁酯 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 甲苯 为溶剂， 反应 23.75h， 生成 tert-butyl 2-[(2R,3R,4R,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-2-(2,4-dioxopyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxyacetate
  参考文献：
  名称：

  Chemical Synthesis and Properties of Conformationally Fixed Diuridine Monophosphates as Building Blocks of the RNA Turn Motif

  摘要：

  Two intramolecularly cyclized diuridine monophosphates having an amide and a carbamate linker have been synthesized for fixation of the LT-turn structure found in various tRNAs and hammerhead ribozymes. The structural analysis of these cyclic dimers using CD, H-1 NMR, and P-31 NMR spectroscopy shows that they have ri,sid, unstacked conformations. Detailed computer simulations of their 3D structures based on molecular mechanics calculations suggest that a two-state equilibrium between a stretch and a turn conformation exists in favor of the former. The simulation also suggested that the diuridine mono-phosphate containing the carbamate-linker is better as a mimic of the U-turn structure than the amide-linked dimer. The enzymatic properties of these cyclized dimers are also described.

  DOI：

  10.1021/jo971797o

文献信息

• Sekine; Seio; Wada, Journal of the American Chemical Society, 1994, vol. 116, # 10, p. 4469 - 4470
  作者：Sekine、Seio、Wada、Sakamoto、Yokoyama

  DOI：——

  日期：——