6-(N,N-diphenylcarbamoyl)oxy-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidine | 329321-59-7

• 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: 6-(N,N-diphenylcarbamoyl)oxy-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidine
• CAS: 329321-59-7
• 化学式: C₄₄H₃₉N₅O₇
• 分子量: 749.823
• InChiKey: HPMMQJLZDAMJPQ-KQIHHXPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.84
• 重原子数：
  56.0
• 可旋转键数：
  12.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  130.29
• 氢给体数：
  1.0
• 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 、 6-(N,N-diphenylcarbamoyl)oxy-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidine 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以68%的产率得到6-(N,N-diphenylcarbamoyl)oxy-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidine 3'-[(2-cyanoethyl)-N,N-diisopropylphosphoramidite]
  参考文献：
  名称：

  Fluorescence Properties and Base Pair Stability of Oligonucleotides Containing 8-Aza-7-deaza-2′-deoxyisoinosine or 2′-Deoxyisoinosine

  摘要：

  The fluorescence and the base pairing properties of 8-aza-7-deaza-2'-deoxyisoinosine (1) are described and compared with those of 2'-deoxyisoinosine (2). The corresponding phosphoramidites (11, 12) are synthesized using the diphenyl-carbamoyl (DPC) residue for the 2-oxo group protection. The nucleosides 1 and 2 base pair with 2'-deoxy-5-methylisocytidine in DNA duplexes with antiparallel chain orientation and with 2'-deoxycytidine in a parallel DNA. These base pairs are less stable than the canonical dA-dT pair and that of 2'-deoxyinosine (4) with 2'-deoxycytidine. The fluorescence of the nucleosides 1 and 2 is quenched (similar to 95%) in duplex DNA. The residual fluorescence is used to determine the T-m-values, which are found to be the same as determined UV-spectrophotometrically.

  DOI：

  10.1080/15257770008045448
• 作为产物：
  描述：

  二苯氨基甲酰氯 在 N,N-二异丙基乙胺 作用下， 以 吡啶 为溶剂， 反应 4.5h， 生成 6-(N,N-diphenylcarbamoyl)oxy-1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Fluorescence Properties and Base Pair Stability of Oligonucleotides Containing 8-Aza-7-deaza-2′-deoxyisoinosine or 2′-Deoxyisoinosine

  摘要：

  The fluorescence and the base pairing properties of 8-aza-7-deaza-2'-deoxyisoinosine (1) are described and compared with those of 2'-deoxyisoinosine (2). The corresponding phosphoramidites (11, 12) are synthesized using the diphenyl-carbamoyl (DPC) residue for the 2-oxo group protection. The nucleosides 1 and 2 base pair with 2'-deoxy-5-methylisocytidine in DNA duplexes with antiparallel chain orientation and with 2'-deoxycytidine in a parallel DNA. These base pairs are less stable than the canonical dA-dT pair and that of 2'-deoxyinosine (4) with 2'-deoxycytidine. The fluorescence of the nucleosides 1 and 2 is quenched (similar to 95%) in duplex DNA. The residual fluorescence is used to determine the T-m-values, which are found to be the same as determined UV-spectrophotometrically.

  DOI：

  10.1080/15257770008045448