4-((3aR,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)benzonitrile | 1050206-86-4

• 分子结构分类: 有机化合物
• 英文名称: 4-((3aR,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)benzonitrile
• CAS: 1050206-86-4
• 化学式: C₃₁H₃₅NO₅Si
• 分子量: 529.708
• InChiKey: HCPBOVQTIDHMLF-WXMBCYQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.94
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-((3aR,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)benzonitrile 、 烯丙基三甲基硅烷 在 zinc dibromide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以40%的产率得到(1R,5R,6S,8R)-3,3-dimethyl-6-(p-cyanophenyl)-6-(2'-propenyl)-8-(tert-butyldiphenylsilyloxymethyl)-2,4,7-trioxabicyclo[3.3.0]octane
  参考文献：
  名称：

  Synthesis of p-amino-WNA derivatives to enhance the stability of the anti-parallel triplex

  摘要：

  We have previously developed W-shaped nucleoside analogs (WNAs) having a nucleobase and an aromatic ring for the formation of the unnatural triplex DNA. Modification of an aromatic ring of WNA is highly effective regarding the stability of the triplex DNA. In this study, we designed new WNA analogs having the p-aminobenzene as an aromatic ring, which were synthesized via the Curtius-Yamada rearrangement. Based on the evaluation of the triplex formation with p-amino-WNA-TFO, it has been shown that the amino group may produce a non-selective interaction with the phosphate backbone of the target duplexes. These results indicate that the amino modification is useful to overcome the sequence-dependence of the TFO containing WNA analogs. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.096
• 作为产物：
  描述：

  4-溴苯腈 、 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 以79%的产率得到4-((3aR,6R,6aR)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)benzonitrile
  参考文献：
  名称：

  Synthesis of p-amino-WNA derivatives to enhance the stability of the anti-parallel triplex

  摘要：

  We have previously developed W-shaped nucleoside analogs (WNAs) having a nucleobase and an aromatic ring for the formation of the unnatural triplex DNA. Modification of an aromatic ring of WNA is highly effective regarding the stability of the triplex DNA. In this study, we designed new WNA analogs having the p-aminobenzene as an aromatic ring, which were synthesized via the Curtius-Yamada rearrangement. Based on the evaluation of the triplex formation with p-amino-WNA-TFO, it has been shown that the amino group may produce a non-selective interaction with the phosphate backbone of the target duplexes. These results indicate that the amino modification is useful to overcome the sequence-dependence of the TFO containing WNA analogs. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.05.096