N-{6-(1-Bromo-vinyl)-1-[(2R,3R,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide | 859838-27-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{6-(1-Bromo-vinyl)-1-[(2R,3R,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide
• 英文别名: N-[6-(1-bromoethenyl)-1-[(2R,3R,4R,5R)-4-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-(2-methoxyethoxy)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 859838-27-0
• 化学式: C₃₃H₅₂BrN₃O₇Si₂
• 分子量: 738.867
• InChiKey: QNUPTBFQZPZTTN-MZAPLOMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  46
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-{6-(1-Bromo-vinyl)-1-[(2R,3R,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.0h， 生成 N⁴-benzoyl-2'-O-(2-methoxyethyl)-6-{1-[2-(ethylthio)]ethyl}cytidine
  参考文献：
  名称：

  Synthesis of reactive cytidine derivatives as building blocks for cross-linking oligonucleotides

  摘要：

  6-Vinvlcytidine derivative (1) possessing good Michael acceptor properties has been synthesized through C-6 formylation and subsequent Wittig reaction. In view of introducing the reactive nucleoside into the oligonucleotide sequence, protection of the vinyl group as ethylthio derivative was proved to be effective for the masking and subsequent regeneration or the reactive vinyl moiety. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.083
• 作为产物：
  描述：

  N-[1-[(2R,3R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-6-(1,2-dibromo-ethyl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 以48%的产率得到N-{6-(1-Bromo-vinyl)-1-[(2R,3R,4R,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-(2-methoxy-ethoxy)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide
  参考文献：
  名称：

  Synthesis of reactive cytidine derivatives as building blocks for cross-linking oligonucleotides

  摘要：

  6-Vinvlcytidine derivative (1) possessing good Michael acceptor properties has been synthesized through C-6 formylation and subsequent Wittig reaction. In view of introducing the reactive nucleoside into the oligonucleotide sequence, protection of the vinyl group as ethylthio derivative was proved to be effective for the masking and subsequent regeneration or the reactive vinyl moiety. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.083