2-methylacrylate-9-[2’-deoxy-3’,5’-O-bis-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]adenine | 1414930-10-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-methylacrylate-9-[2’-deoxy-3’,5’-O-bis-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]adenine
• CAS: 1414930-10-1
• 化学式: C₂₆H₄₅N₅O₅Si₂
• 分子量: 563.845
• InChiKey: ZFVLPMQWMIMDPC-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.29
• 重原子数：
  38.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  123.61
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-methylacrylate-9-[2’-deoxy-3’,5’-O-bis-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]adenine 在 吡啶 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 27.0h， 生成 2-(1-methylester-2-octylthioethyl)-6-phenoxyacetylamino-9-[2-deoxy-3’,5’-O-bis-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]purine
  参考文献：
  名称：

  Synthesis of 6-amino-2-vinylpurine derivatives for cross-linking and evaluation of the reactivity

  摘要：

  Oligodeoxynucleotides (ODNs) have been widely used for inhibiting the gene expression in antisense or antigene methods, and the interstrand cross-linking (ICL) forming ODNs have been expected to ensure the inhibition by these methods. Previously, we reported a highly efficient and selective ICL reaction toward cytosine using the 2-amino-6-vinylpurine derivative under acidic conditions. In this Letter, we report the synthesis of ODN containing 6-amino-2-vinylpurine derivatives and evaluation of the cross-linking reactivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.122
• 作为产物：
  描述：

  2-(三丁基锡烷基)-2-丙烯酸甲酯 、 2-iodo-9-<2-deoxy-3,5-O-bis-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>adenine 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以71%的产率得到2-methylacrylate-9-[2’-deoxy-3’,5’-O-bis-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]adenine
  参考文献：
  名称：

  Synthesis of 6-amino-2-vinylpurine derivatives for cross-linking and evaluation of the reactivity

  摘要：

  Oligodeoxynucleotides (ODNs) have been widely used for inhibiting the gene expression in antisense or antigene methods, and the interstrand cross-linking (ICL) forming ODNs have been expected to ensure the inhibition by these methods. Previously, we reported a highly efficient and selective ICL reaction toward cytosine using the 2-amino-6-vinylpurine derivative under acidic conditions. In this Letter, we report the synthesis of ODN containing 6-amino-2-vinylpurine derivatives and evaluation of the cross-linking reactivity. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.122