3',3'-butadiynediyl-[(2,5-di-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-uracil]-[(2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-adenine] | 501428-36-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 3',3'-butadiynediyl-[(2,5-di-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-uracil]-[(2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-adenine]
• 英文别名: 1-[(2R,3R,4R,5R)-4-[4-[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-4-[tert-butyl(dimethyl)silyl]oxy-3-hydroxy-2-(hydroxymethyl)oxolan-3-yl]buta-1,3-diynyl]-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 501428-36-0
• 化学式: C₄₁H₆₅N₇O₁₀Si₃
• 分子量: 900.264
• InChiKey: NTBPGVIHYOHTST-YLNLJNIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  61
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  226
• 氢给体数：
  5
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  3',3'-butadiynediyl-[(2,5-di-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-uracil]-[(2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-adenine] 在 氟化铵 作用下， 以 甲醇 为溶剂， 以52%的产率得到3',3'-butadiynediyl-[(β-D-ribofuranosyl)-uracil-(β-D-ribofuranosyl)-adenine]
  参考文献：
  名称：

  Synthesis of Nucleoside Dimers Bridged on Ribose with a Butadiynyl Group

  摘要：

  [GRAPHICS]The nucleoside dimer linked by a butadiynediyl group at C-3'beta may serve as a building block for the preparation of backbone-modified oligonucleotides for DNA repair or mutation in functional genomics. We prepared this type of dimer by an Eglington or Sonogashira coupling reaction. The unsymmetrical dimer was synthesized by coupling the acetylene with the bromoacetylene. Only marginal cytotoxicity was detected for one of the dimers.

  DOI：

  10.1021/ol026584m
• 作为产物：
  描述：

  1-[2,5-di-O-(tert-butyldimethylsilyl)-3-C-ethynyl-β-D-ribo-pentofuranosyl]uracil 在 tris(dibenzylideneacetone)dipalladium (0) 1,2,2,6,6-五甲基哌啶 、 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 silver nitrate 、 lithium iodide 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 49.0h， 生成 3',3'-butadiynediyl-[(2,5-di-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-uracil]-[(2-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl)-adenine]
  参考文献：
  名称：

  Synthesis of Nucleoside Dimers Bridged on Ribose with a Butadiynyl Group

  摘要：

  [GRAPHICS]The nucleoside dimer linked by a butadiynediyl group at C-3'beta may serve as a building block for the preparation of backbone-modified oligonucleotides for DNA repair or mutation in functional genomics. We prepared this type of dimer by an Eglington or Sonogashira coupling reaction. The unsymmetrical dimer was synthesized by coupling the acetylene with the bromoacetylene. Only marginal cytotoxicity was detected for one of the dimers.

  DOI：

  10.1021/ol026584m

文献信息

• Synthesis of Nucleoside Dimers Bridged on Ribose with a Butadiynyl Group
  作者：Françoise Jung、Alain Burger、Jean-François Biellmann

  DOI：10.1021/ol026584m

  日期：2003.2.1

  [GRAPHICS]The nucleoside dimer linked by a butadiynediyl group at C-3'beta may serve as a building block for the preparation of backbone-modified oligonucleotides for DNA repair or mutation in functional genomics. We prepared this type of dimer by an Eglington or Sonogashira coupling reaction. The unsymmetrical dimer was synthesized by coupling the acetylene with the bromoacetylene. Only marginal cytotoxicity was detected for one of the dimers.