1'-ethynyl-2'-deoxy-D-ribose | 1000889-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1'-ethynyl-2'-deoxy-D-ribose
• 英文别名: (2R,3S)-5-ethynyl-2-(hydroxymethyl)oxolan-3-ol
• CAS: 1000889-58-6
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: UEUAGEBCJFIFCU-BOJSHJERSA-N

物化性质

• 沸点：
  286.9±40.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2R,3S)-5-ethynyl-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到1'-ethynyl-2'-deoxy-D-ribose
  参考文献：
  名称：

  具有1个取代的1 H -1,2,3-三唑的C-核苷酸的合成和碱基配对性质

  摘要：

  寡核苷酸包括具有C-核苷酸1-取代的1个ħ 1,2,3-三唑作为人造核碱基被方便地通过使用铜（I） -催化的炔叠氮化1,3-偶极环加成（后伸长修改方法合成CuAAC）反应。通过T m实验研究了三唑核碱基类似物在与寡核苷酸形成双链体中的碱基配对特性。

  DOI：

  10.1016/j.bmcl.2009.04.063

文献信息

• Synthesis and base-pairing properties of C-nucleotides having 1-substituted 1H-1,2,3-triazoles
  作者：Motoi Nakahara、Takeshi Kuboyama、Akihiro Izawa、Yoshiyuki Hari、Takeshi Imanishi、Satoshi Obika

  DOI：10.1016/j.bmcl.2009.04.063

  日期：2009.6

  artificial nucleobases were conveniently synthesized by the post-elongation modification method using the copper(I)-catalyzed alkyne–azide 1,3-dipolar cycloaddition (CuAAC) reaction. The base-pairing properties of the triazole nucleobase analogs in forming duplexes with oligonucleotides were investigated by the Tm experiments.

  寡核苷酸包括具有C-核苷酸1-取代的1个ħ 1,2,3-三唑作为人造核碱基被方便地通过使用铜（I） -催化的炔叠氮化1,3-偶极环加成（后伸长修改方法合成CuAAC）反应。通过T m实验研究了三唑核碱基类似物在与寡核苷酸形成双链体中的碱基配对特性。
• 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.