8-bromo-N⁶-phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine | 143660-33-7

• 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: 8-bromo-N⁶-phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine
• CAS: 143660-33-7
• 化学式: C₃₉H₃₆BrN₅O₇
• 分子量: 766.648
• InChiKey: PWRQBFSDPFGKGA-VOTWKOMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  52.0
• 可旋转键数：
  13.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  139.08
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  双(二异丙基氨基)(2-氰基乙氧基)膦 、 8-bromo-N⁶-phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine 在 二异丙基铵盐四氮唑 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到8-bromo-N⁶-phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine-3'O-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
  参考文献：
  名称：

  Synthesis of photoactive DNA: incorporation of 8-bromo-2′-deoxyadenosine into synthetic oligodeoxynucleotides

  摘要：

  8-Bromo-N6-phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine-3'-O-(2-cyanoethyl-N,N-diisopropyl) phosphoramidite was synthesized and used to introduce 8-bromo-2'-deoxyadenosine (8-Br-dA) into oligodeoxynucleotides by means of automated synthesis. 8-Br-dA was found not to affect adversely the stability of duplex DNA, as judged by the melting behavior of several 8-Br-dA-containing duplexes.

  DOI：

  10.1016/s0040-4039(00)74234-1
• 作为产物：
  描述：

  在 吡啶 、 水 、 三乙胺 作用下， 反应 2.08h， 生成 8-bromo-N⁶-phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis of photoactive DNA: incorporation of 8-bromo-2′-deoxyadenosine into synthetic oligodeoxynucleotides

  摘要：

  8-Bromo-N6-phenoxyacetyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxyadenosine-3'-O-(2-cyanoethyl-N,N-diisopropyl) phosphoramidite was synthesized and used to introduce 8-bromo-2'-deoxyadenosine (8-Br-dA) into oligodeoxynucleotides by means of automated synthesis. 8-Br-dA was found not to affect adversely the stability of duplex DNA, as judged by the melting behavior of several 8-Br-dA-containing duplexes.

  DOI：

  10.1016/s0040-4039(00)74234-1