3'-O-[(tert-butyl)dimethylsilyl]-5'-O-(2-oxoethyl)thymidine | 929075-71-8

• 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: 3'-O-[(tert-butyl)dimethylsilyl]-5'-O-(2-oxoethyl)thymidine
• 英文别名: 5'-O-methylenecarbaldehyde-3'-O-(tert-butyldimethylsilyl)thymidine；2-[[(2R,3S,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]acetaldehyde
• CAS: 929075-71-8
• 化学式: C₁₈H₃₀N₂O₆Si
• 分子量: 398.531
• InChiKey: UHDQQOQHFWFBOO-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3'-O-[(tert-butyl)dimethylsilyl]-5'-O-(2-oxoethyl)thymidine 在 sodium acetate 、 溶剂黄146 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  DNA‐Templated Formation and N,O‐Transacetalization of N‐Methoxyoxazolidines

  摘要：

  AbstractDNA‐templated formation and N,O‐transacetalization of N‐methoxyoxazolidines have been studied. Compared to the reaction without a DNA‐catalyst, the hybridization‐driven N‐methoxyoxazolidine formation shows a marked rate acceleration, whereas the rate of corresponding N,O‐transacetalization is limited by the rate of decay to aldehyde intermediates. In both cases, the equilibrium yield increases markedly on the DNA template. Different hairpin architectures have been studied to evaluate the role and limits of the template effect. Furthermore, an attention has been paid to stereochemical integrity (R/S) of the N‐methoxyoxazolidine linkage. The N‐methoxyoxazolidine formation represents a dynamic pH‐responsive DNA‐templated ligation that occurs readily in slightly acidic conditions (pH 5).

  DOI：

  10.1002/ejoc.202200583
• 作为产物：
  描述：

  5'-O-(prop-2-enyl)thymidine 在 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 1.0h， 生成 3'-O-[(tert-butyl)dimethylsilyl]-5'-O-(2-oxoethyl)thymidine
  参考文献：
  名称：

  DNA‐Templated Formation and N,O‐Transacetalization of N‐Methoxyoxazolidines

  摘要：

  AbstractDNA‐templated formation and N,O‐transacetalization of N‐methoxyoxazolidines have been studied. Compared to the reaction without a DNA‐catalyst, the hybridization‐driven N‐methoxyoxazolidine formation shows a marked rate acceleration, whereas the rate of corresponding N,O‐transacetalization is limited by the rate of decay to aldehyde intermediates. In both cases, the equilibrium yield increases markedly on the DNA template. Different hairpin architectures have been studied to evaluate the role and limits of the template effect. Furthermore, an attention has been paid to stereochemical integrity (R/S) of the N‐methoxyoxazolidine linkage. The N‐methoxyoxazolidine formation represents a dynamic pH‐responsive DNA‐templated ligation that occurs readily in slightly acidic conditions (pH 5).

  DOI：

  10.1002/ejoc.202200583

文献信息

• Synthesis and Hybridization Properties of Oligodeoxynucleotides with Long-Chain Linkers
  作者：Kohji Seio、Takeshi Terada、Masahiro Mizuta、Akihiro Ohkubo、Haruhiko Taguchi、Mitsuo Sekine

  DOI：10.1002/hlca.200790203

  日期：2007.10

  their backbone were synthesized, and their hybridization properties were studied by measurement of their Tm curves and fluorescence spectra. The Tm analyses revealed that these oligonucleotides could bind to their complementary strands despite the presence of the long-chain linker. We also demonstrated interesting fluorescence properties of oligodeoxynucleotides with an anthracen-9-ylmethyl group on one

  在其主链的长链连接基（6,9-二氧杂-3,12- diazatetradecane -1,14-二基）新合成寡核苷酸，并可以通过测量进行了研究其杂交性质Ť米曲线和荧光光谱。所述Ť米分析表明，这些寡核苷酸可以结合它们的互补链，尽管长链连接基的存在。我们还证明了在长链接头中两个N原子之一上具有蒽9-基甲基的寡聚脱氧核苷酸的有趣荧光性质。这些寡核苷酸与互补链杂交后，其荧光强度增加，并且对特定位置错配碱基对的存在敏感。
• DNA‐Templated Formation and N,O‐Transacetalization of N‐Methoxyoxazolidines
  作者：Aapo Aho、Tommi Österlund、Jani Rahkila、Pasi Virta

  DOI：10.1002/ejoc.202200583

  日期：2022.8.19

  AbstractDNA‐templated formation and N,O‐transacetalization of N‐methoxyoxazolidines have been studied. Compared to the reaction without a DNA‐catalyst, the hybridization‐driven N‐methoxyoxazolidine formation shows a marked rate acceleration, whereas the rate of corresponding N,O‐transacetalization is limited by the rate of decay to aldehyde intermediates. In both cases, the equilibrium yield increases markedly on the DNA template. Different hairpin architectures have been studied to evaluate the role and limits of the template effect. Furthermore, an attention has been paid to stereochemical integrity (R/S) of the N‐methoxyoxazolidine linkage. The N‐methoxyoxazolidine formation represents a dynamic pH‐responsive DNA‐templated ligation that occurs readily in slightly acidic conditions (pH 5).