2-(2-methylthioethyl)-6-phenoxyacetylamino-9-[2’-deoxy-5’-O-(4,4’-dimethoxytrityl)-β-D-ribofuranosyl]purine | 1414930-08-7

• 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-(2-methylthioethyl)-6-phenoxyacetylamino-9-[2’-deoxy-5’-O-(4,4’-dimethoxytrityl)-β-D-ribofuranosyl]purine
• CAS: 1414930-08-7
• 化学式: C₄₂H₄₃N₅O₇S
• 分子量: 761.899
• InChiKey: MDPVZVROUCEYIO-FACBKIGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  55.0
• 可旋转键数：
  16.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  139.08
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  2-(2-methylthioethyl)-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29%的产率得到2-(2-methylthioethyl)-6-phenoxyacetylamino-1-[2-(2’deoxy-3’-N,N-diisopropyl cyanoethylphosphoramidyl)-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-iodo-9-<2-deoxy-3,5-O-bis-(tert-butyldimethylsilyl)-β-D-ribofuranosyl>adenine 在 吡啶 、 双(乙腈)氯化钯(II) 、 四丁基氟化铵 、 1-羟基苯并三唑 作用下， 以 四氢呋喃 、 吡啶 、 水 、 乙腈 为溶剂， 反应 104.5h， 生成 2-(2-methylthioethyl)-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