4-[[1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-hydroxymethyl]benzonitrile | 213037-77-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 4-[[1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-hydroxymethyl]benzonitrile
• CAS: 213037-77-5
• 化学式: C₂₉H₄₅N₃O₆Si₂
• 分子量: 587.864
• InChiKey: TXLWTYADEWWTLD-QPDXQIEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  126.57
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-[[1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-hydroxymethyl]benzonitrile 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-[1-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-2,4-dioxopyrimidine-5-carbonyl]benzonitrile
  参考文献：
  名称：

  p-Cyano substituted 5-benzoyldeoxyuridine as a novel electron-accepting nucleobase for one-electron oxidation of DNA

  摘要：

  p-Cyano substituted 5-benzoyl-2'-deoxyuridine 1 was synthesized as a novel electron-accepting nucleobase. DNA cleavage by 1 under photoirradiation conditions occurred selectively at the 5'-G of 5'GG3' sequences after hot piperidine treatment. Photoirradiation of 1 in the presence of dG produced imidazolone as a major product. The electron-accepting nucleobase 1 was successfully incorporated into DNA oligomer by automated DNA synthesis using phosporamidite 2. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01231-3
• 作为产物：
  描述：

  3',5'-O-di(tert-butyldimethylsilyl)-2'-deoxyuridine 、 4-氰基苯甲醛 在 四甲基乙二胺 、 仲丁基锂 作用下， 以 四氢呋喃 为溶剂， 以38%的产率得到4-[[1-[(2R,4S,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]oxolan-2-yl]-2,4-dioxopyrimidin-5-yl]-hydroxymethyl]benzonitrile
  参考文献：
  名称：

  p-Cyano substituted 5-benzoyldeoxyuridine as a novel electron-accepting nucleobase for one-electron oxidation of DNA

  摘要：

  p-Cyano substituted 5-benzoyl-2'-deoxyuridine 1 was synthesized as a novel electron-accepting nucleobase. DNA cleavage by 1 under photoirradiation conditions occurred selectively at the 5'-G of 5'GG3' sequences after hot piperidine treatment. Photoirradiation of 1 in the presence of dG produced imidazolone as a major product. The electron-accepting nucleobase 1 was successfully incorporated into DNA oligomer by automated DNA synthesis using phosporamidite 2. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01231-3