5'-O-tert-butyldiphenylsilyl-8-[(anthraquinon-2-yl)ethynyl]-2'-deoxyadenosine | 868383-12-4

• 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: 5'-O-tert-butyldiphenylsilyl-8-[(anthraquinon-2-yl)ethynyl]-2'-deoxyadenosine
• CAS: 868383-12-4
• 化学式: C₄₂H₃₇N₅O₅Si
• 分子量: 719.872
• InChiKey: OQQLTIVFASVDIR-GABYNLOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  53.0
• 可旋转键数：
  6.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  142.45
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5'-O-tert-butyldiphenylsilyl-8-[(anthraquinon-2-yl)ethynyl]-2'-deoxyadenosine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 24.0h， 以86%的产率得到5'-O-tert-butyldiphenylsilyl-8-[(anthraquinon-2-yl)ethyl]-2'-deoxyadenosine
  参考文献：
  名称：

  两种 8-[(Anthraquinone-2-yl)-Linked]-2'-脱氧腺苷 3'-苄基磷酸氢盐的合成用于研究 DNA 中的光诱导空穴传输

  摘要：

  The challenge in working with anthraquinone-2'-deoxyadenosine (AQ-dA) conjugates is that they are insoluble in water and only sparingly soluble in most organic solvents. However, water-soluble AQ-dA conjugates with short linkers are required for study of their electrochemical and intramolecular electron transfer Properties in this solvent prior to their use in laser kinetics investigations of photoinduced hole (cation) transport in DNA. This article first describes the synthesis Of a water-soluble, ethynyl-linked AQ-dA conjugate, 8-[(anthraquinone-2-yl)ethynyl]-2'-deoxyadenosine 3'-benzyl hydrogen phosphate, based on initial formation of a 5-O-(4,4'-dimethoxytrityl) (5'-O-DMTr) intermediate. Because intended H-2 over Pd/C reduction of the ethyryl linker in 5-O-DMTr-protected 2'-deoxyadenosines cleaves the DMTr protecting group and precipitates multiple side products, this work also describes the synthesis Of an ethylenyl-linked AQ-dA conjugate, 8-[2-(anthraquinone-2-yl)ethyl]-2'-deoxyadenosine 3'-benzyl hydrogen phosphate, starting with a 5-O-tert-butyldiphenylsilyl protecting group.

  DOI：

  10.1081/ncn-200051894
• 作为产物：
  描述：

  2'-脱氧腺苷 在 四(三苯基膦)钯 吡啶 、 copper(l) iodide 、 TEA 、 溴 作用下， 以 acetate buffer 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 5'-O-tert-butyldiphenylsilyl-8-[(anthraquinon-2-yl)ethynyl]-2'-deoxyadenosine
  参考文献：
  名称：

  两种 8-[(Anthraquinone-2-yl)-Linked]-2'-脱氧腺苷 3'-苄基磷酸氢盐的合成用于研究 DNA 中的光诱导空穴传输

  摘要：

  The challenge in working with anthraquinone-2'-deoxyadenosine (AQ-dA) conjugates is that they are insoluble in water and only sparingly soluble in most organic solvents. However, water-soluble AQ-dA conjugates with short linkers are required for study of their electrochemical and intramolecular electron transfer Properties in this solvent prior to their use in laser kinetics investigations of photoinduced hole (cation) transport in DNA. This article first describes the synthesis Of a water-soluble, ethynyl-linked AQ-dA conjugate, 8-[(anthraquinone-2-yl)ethynyl]-2'-deoxyadenosine 3'-benzyl hydrogen phosphate, based on initial formation of a 5-O-(4,4'-dimethoxytrityl) (5'-O-DMTr) intermediate. Because intended H-2 over Pd/C reduction of the ethyryl linker in 5-O-DMTr-protected 2'-deoxyadenosines cleaves the DMTr protecting group and precipitates multiple side products, this work also describes the synthesis Of an ethylenyl-linked AQ-dA conjugate, 8-[2-(anthraquinone-2-yl)ethyl]-2'-deoxyadenosine 3'-benzyl hydrogen phosphate, starting with a 5-O-tert-butyldiphenylsilyl protecting group.

  DOI：

  10.1081/ncn-200051894