2-(1-methylester-2-octylthioethyl)-6-phenoxyacetylamino-9-(2-deoxy-5’-O-(4,4’-dimethoxytrityl)-β-D-ribofuranosyl)purine | 1414930-14-5

• 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: 2-(1-methylester-2-octylthioethyl)-6-phenoxyacetylamino-9-(2-deoxy-5’-O-(4,4’-dimethoxytrityl)-β-D-ribofuranosyl)purine
• CAS: 1414930-14-5
• 化学式: C₅₁H₅₉N₅O₉S
• 分子量: 918.124
• InChiKey: VHZJQQAORYJRSP-TYTADZHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.87
• 重原子数：
  66.0
• 可旋转键数：
  24.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  165.38
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2-(1-methylester-2-octylthioethyl)-6-phenoxyacetylamino-9-(2-deoxy-5’-O-(4,4’-dimethoxytrityl)-β-D-ribofuranosyl)purine 、 chloro-(2-cyanoethyl)-diisopropylaminophosphane 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以48%的产率得到2-(1-methylester-2-octylthioethyl)-6-phenoxyacetylamino-9-[2-(2’deoxy-3’-N,N-diisopropylcyanoethylphosphoramidyl)-5’-O-(4,4’-dimethoxytrityl)-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-(1-methylester-2-octylthioethyl)-9-[2-deoxy-3’,5’-O-bis-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]adenine 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 2-(1-methylester-2-octylthioethyl)-6-phenoxyacetylamino-9-(2-deoxy-5’-O-(4,4’-dimethoxytrityl)-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