(1R,3R,4R,7S)-3-(N3-benzoylthymin-1-yl)-1-dimethoxytrityloxymethyl-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane | 1581258-53-8

• 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: (1R,3R,4R,7S)-3-(N3-benzoylthymin-1-yl)-1-dimethoxytrityloxymethyl-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane
• 英文别名: (1R,3R,4R,7S)-3-(N³-benzoylthymin-1-yl)-1-dimethoxytrityloxymethyl-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane
• CAS: 1581258-53-8
• 化学式: C₃₉H₃₆N₂O₉
• 分子量: 676.723
• InChiKey: HEXYXFPLJNZNJP-OSZGUBSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  50.0
• 可旋转键数：
  10.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  127.45
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  pyridinium H-boranophosphonate 、 (1R,3R,4R,7S)-3-(N3-benzoylthymin-1-yl)-1-dimethoxytrityloxymethyl-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptane 、 三乙基碳酸氢铵缓冲液 在 吡啶 、 双(2-氧代-3-恶唑烷基)次磷酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以75%的产率得到triethylammonium (1R,3R,4R,7S)-3-(N³-benzoylthymin-1-yl)-1-dimethoxytrityloxymethyl-2,5-dioxabicyclo[2.2.1]heptane-7-H-boranophosphonate
  参考文献：
  名称：

  Solid-Phase Synthesis of P-Boronated Oligonucleotides by the H-Boranophosphonate Method

  摘要：

  Recently, P-boronated oligonucleotides have been attracting much attention as potential therapeutic oligonucleotides. In this study, we developed H-boranophosphonate oligonucleotide bearing a borano group and hydrogen atom on the intemucleotidic phosphorus and demonstrated that this novel P-boronated oligonucleotide is a versatile precursor to various P-boronated oligonucleotides such as boranophosphate, boranophosphorothioate, and boranophosphoramidate. The method was also applicable to the synthesis of a locked nucleic acid-modified boranophosphate oligonucleotide, which exhibited a dramatically enhanced affinity to complementary oligonucleotides.

  DOI：

  10.1021/jo500185b