2-(1-methylester-2-octylthioethyl)-9-[2-deoxy-3’,5’-O-bis-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]adenine | 1414930-11-2

• 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-(1-methylester-2-octylthioethyl)-9-[2-deoxy-3’,5’-O-bis-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]adenine
• 英文别名: methyl 2-[6-amino-9-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]purin-2-yl]-3-octylsulfanylpropanoate
• CAS: 1414930-11-2
• 化学式: C₃₄H₆₃N₅O₅SSi₂
• 分子量: 710.142
• InChiKey: SJTZAYWPANLYPP-ZHOVUOCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.46
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  149
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  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 28.0h， 生成 2-(1-methylester-2-octylthioethyl)-6-phenoxyacetylamino-9-(2-deoxy-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 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 6.0h， 生成 2-(1-methylester-2-octylthioethyl)-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

文献信息

• Synthesis of 6-amino-2-vinylpurine derivatives for cross-linking and evaluation of the reactivity
  作者：Shuhei Kusano、Tomoya Sakuraba、Shinya Hagihara、Fumi Nagatsugi

  DOI：10.1016/j.bmcl.2012.08.122

  日期：2012.11

  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.