N⁶-benzoyl-9-[(2'S,3'R)-2'-tert-butyldimethylsiloxy-3'-hydroxy-4'-(4,4'-dimethoxytrityloxy)butyl]adenine | 765912-08-1

• 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: N⁶-benzoyl-9-[(2'S,3'R)-2'-tert-butyldimethylsiloxy-3'-hydroxy-4'-(4,4'-dimethoxytrityloxy)butyl]adenine
• CAS: 765912-08-1
• 化学式: C₄₃H₄₉N₅O₆Si
• 分子量: 759.977
• InChiKey: NVBQXPLXZKKUPV-AARKOHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.86
• 重原子数：
  55.0
• 可旋转键数：
  15.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  129.85
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 N⁶-benzoyl-9-[(2'S,3'R)-2'-tert-butyldimethylsiloxy-3'-hydroxy-4'-(4,4'-dimethoxytrityloxy)butyl]adenine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到N⁶-benzoyl-9-[(2'S,3'R)-2'-tert-butyldimethylsiloxy-4'-(4,4'-dimethoxytrityloxy)butyl]adenine-3'-[O-(2-cyanoethyl)-N,N-diisopropylphosphoamidite]
  参考文献：
  名称：

  含有（2S，3R）-9-（2，3，4-三羟基丁基）腺嘌呤的寡核苷酸的合成和杂交特性。

  摘要：

  描述了包含9-（2,3,4-三羟基丁基）腺嘌呤，A（C2）和A（C3）的寡核苷酸（ON）的合成和性质。含A（C2）的ON涉及链中的3'-> 4'和3-> 5'磷酸二酯键，而含A（C3）的ON具有3'-> 4'和2'- > 5'磷酸二酯键。发现将类似物A（C2）或A（C3）掺入ON中会显着降低ON / DNA双链体的热稳定性和热力学稳定性，但不会大大降低ON / RNA的热稳定性和热力学稳定性与ON / DNA双链体的情况相比。揭示了在ON / RNA双链体中，A（C2）的碱基识别能力大于A（C3）的碱基识别能力。

  DOI：

  10.1080/15257770600684175
• 作为产物：
  描述：

  9-[(2'S,3'R)-4'-hydroxy-2',3'-isopropylidenedioxybutyl]adenine 在 吡啶 、 咪唑 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N⁶-benzoyl-9-[(2'S,3'R)-2'-tert-butyldimethylsiloxy-3'-hydroxy-4'-(4,4'-dimethoxytrityloxy)butyl]adenine
  参考文献：
  名称：

  Synthesis of 2′,5′-oligoadenylate analogs containing an adenine acyclonucleoside and their ability to activate human RNase L

  摘要：

  This paper described synthesis of 2',5'-oligoadenylate (2-5A) analogs containing the purine acyclonucleoside, 9[(2'S,3'R)-2',3',4'-trihydroxybutyl]adenine (2). The ability of the analogs to activate recombinant human RNase L was evaluated using 5'-(32) P-r(C11U2C7)(-3)' as a substrate. The EC50 value (the concentration of the 2-5A required to cleave half of the RNA) of the parent 2-5A tetramer 13 was 1.0nM, whereas those of the analog 14 incorporating 2 at the second position from the 5'-end and the analog 15 incorporating 2 at the third position from the 5'-end were 9.0 and 1.7nM, respectively. The analogs 14 and 15 were only 9- and 1.7-fold less potent than the parent 2-5A 13 itself, in RNase L activation ability. Furthermore, the oligodeoxynucleotide containing 2 was more resistant to nucleolytic hydrolysis by snake venom phosphodiesterase (a 3'-exonuclease) than the unmodified oligodeoxynucleotide. Thus, incorporation of an acyclonucleoside into 2-5A may be useful for developing an antiviral agent based on the 2-5A system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.06.071