3',5'-di(tert-butyldimethylsiloxy)-1'-ethynyl-2'-deoxy-D-ribose | 1000889-60-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3',5'-di(tert-butyldimethylsiloxy)-1'-ethynyl-2'-deoxy-D-ribose
• 英文别名: tert-butyl-[[(2R,3S)-3-[tert-butyl(dimethyl)silyl]oxy-5-ethynyloxolan-2-yl]methoxy]-dimethylsilane
• CAS: 1000889-60-0
• 化学式: C₁₉H₃₈O₃Si₂
• 分子量: 370.68
• InChiKey: WQXSQAYJOQVZPD-LRUHZDSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-碘胞核嘧啶 、 3',5'-di(tert-butyldimethylsiloxy)-1'-ethynyl-2'-deoxy-D-ribose 在 四(三苯基膦)钯 硫酸氢铵 、 六甲基二硅氮烷 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以55%的产率得到2-(cytosin-5-yl)-1-(3',5'-di(tert-butyldimethylsiloxy)-2'-deoxy-pentofuranosyl)ethyne
  参考文献：
  名称：

  Synthesis and DNA Incorporation of an Ethynyl-Bridged Cytosine C-Nucleoside as Guanosine Surrogate

  摘要：

  As a guanosine mimic that lacks the preference for syn or anti conformation a cytosine C-nucleoside was synthesized connecting the nucleobase at the anomeric center by an ethynyl linker. The key step was a Sonogashira cross coupling of 5-iodocytosine with 1 '-ethynyl-2 '-deoxyribose. The new C-nucleoside incorporated into G/C-alternating oligonucleotides emerged as guanosine substitute, however, with reduced duplex stability. B-Form DNA was strongly stabilized by the new surrogate even in typically Z-DNA forming sequences and in Z-form inducing environment.

  DOI：

  10.1021/ol7025334
• 作为产物：
  描述：

  1'-ethynyl-2'-deoxy-D-ribose 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以100%的产率得到3',5'-di(tert-butyldimethylsiloxy)-1'-ethynyl-2'-deoxy-D-ribose
  参考文献：
  名称：

  Synthesis and DNA Incorporation of an Ethynyl-Bridged Cytosine C-Nucleoside as Guanosine Surrogate

  摘要：

  As a guanosine mimic that lacks the preference for syn or anti conformation a cytosine C-nucleoside was synthesized connecting the nucleobase at the anomeric center by an ethynyl linker. The key step was a Sonogashira cross coupling of 5-iodocytosine with 1 '-ethynyl-2 '-deoxyribose. The new C-nucleoside incorporated into G/C-alternating oligonucleotides emerged as guanosine substitute, however, with reduced duplex stability. B-Form DNA was strongly stabilized by the new surrogate even in typically Z-DNA forming sequences and in Z-form inducing environment.

  DOI：

  10.1021/ol7025334

文献信息

• Synthesis and DNA Incorporation of an Ethynyl-Bridged Cytosine <i>C</i>-Nucleoside as Guanosine Surrogate
  作者：Daniel Heinrich、Thomas Wagner、Ulf Diederichsen

  DOI：10.1021/ol7025334

  日期：2007.12.1

  As a guanosine mimic that lacks the preference for syn or anti conformation a cytosine C-nucleoside was synthesized connecting the nucleobase at the anomeric center by an ethynyl linker. The key step was a Sonogashira cross coupling of 5-iodocytosine with 1 '-ethynyl-2 '-deoxyribose. The new C-nucleoside incorporated into G/C-alternating oligonucleotides emerged as guanosine substitute, however, with reduced duplex stability. B-Form DNA was strongly stabilized by the new surrogate even in typically Z-DNA forming sequences and in Z-form inducing environment.