5-(1-(4-tert-butyldimethylsilyloxyphenyl)-1,2,3-triazol-4-yl)-5'-(4,4'-dimethoxytrityl)-3'-O-(P-(2-cyanoethoxy)-N,N-diisopropylaminophosphinyl)-2'-deoxyuridine | 1146145-11-0

• 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: 5-(1-(4-tert-butyldimethylsilyloxyphenyl)-1,2,3-triazol-4-yl)-5'-(4,4'-dimethoxytrityl)-3'-O-(P-(2-cyanoethoxy)-N,N-diisopropylaminophosphinyl)-2'-deoxyuridine
• CAS: 1146145-11-0
• 化学式: C₅₃H₆₆N₇O₉PSi
• 分子量: 1004.21
• InChiKey: PXLLONIMQQEUQQ-KQOGYRKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.14
• 重原子数：
  71.0
• 可旋转键数：
  21.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  177.21
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  5-(1-(4-tert-butyldimethylsilyloxyphenyl)-1,2,3-triazol-4-yl)-5'-(4,4'-dimethoxytrityl)-2'-deoxyuridine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以74%的产率得到5-(1-(4-tert-butyldimethylsilyloxyphenyl)-1,2,3-triazol-4-yl)-5'-(4,4'-dimethoxytrityl)-3'-O-(P-(2-cyanoethoxy)-N,N-diisopropylaminophosphinyl)-2'-deoxyuridine
  参考文献：
  名称：

  Efficient RNA-targeting by the introduction of aromatic stacking in the duplex major groove via 5-(1-phenyl-1,2,3-triazol-4-yl)-2′-deoxyuridines

  摘要：

  Three pyrimidine nucleosides with differently substituted phenyltriazoles attached to the 5-position were prepared by Cu(I)-assisted azide-alkyne cycloadditions (CuAAC) and incorporated into oligonucleotides. Efficient pi-pi-stacking between two or more phenyltriazoles in the major groove was found to increase the thermal stability of a DNA: RNA duplex significantly. The best stacking, and most stable duplex, was obtained by a sulfonamide substituted derivative. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.019