5'-O-tert-butyldiphenylsilyl-8-[(anthraquinon-2-yl)ethyl]-2'-deoxyadenosine 3'-dibenzyl phosphate | 868383-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 5'-O-tert-butyldiphenylsilyl-8-[(anthraquinon-2-yl)ethyl]-2'-deoxyadenosine 3'-dibenzyl phosphate
• CAS: 868383-14-6
• 化学式: C₅₆H₅₄N₅O₈PSi
• 分子量: 984.133
• InChiKey: QZZLPZXMGUOGNT-ZESSXDSKSA-N

反应信息

• 作为反应物：
  描述：

  5'-O-tert-butyldiphenylsilyl-8-[(anthraquinon-2-yl)ethyl]-2'-deoxyadenosine 3'-dibenzyl phosphate 在 氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 以88%的产率得到8-[(anthraquinon-2-yl)ethyl]-2'-deoxyadenosine 3'-dibenzyl phosphate
  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：

  在 二氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以833 mg的产率得到5'-O-tert-butyldiphenylsilyl-8-[(anthraquinon-2-yl)ethyl]-2'-deoxyadenosine 3'-dibenzyl phosphate
  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