6-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6H-thieno[2,3-c]pyridin-7-one | 849765-66-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6H-thieno[2,3-c]pyridin-7-one
• CAS: 849765-66-8
• 化学式: C₁₂H₁₃NO₄S
• 分子量: 267.306
• InChiKey: FHLMULZOECOJFR-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  71.69
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6H-thieno[2,3-c]pyridin-7-one 在 磷酸三甲酯 、 Proton Sponge 、 三氯氧磷 、 三正丁胺 、 三丁基焦磷酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.02h， 生成
  参考文献：
  名称：

  Determinants of Unnatural Nucleobase Stability and Polymerase Recognition

  摘要：

  Six new unnatural nucleobases have been synthesized and characterized in terms of stability and selectivity of self-pairing in duplex DNA and efficiency and fidelity of self-pairing during polymerase-mediated replication. Each nucleobase has a conserved ring structure but differs from the others in its specific pattern of substitution with oxygen and sulfur atoms. Heteroatom derivatization within the conserved scaffold is shown to have only moderate effects on unnatural self-pair synthesis by the polymerase; larger effects were observed on the thermal stability and polymerase-mediated extension of the self-pairs. The largest effects of heteroatom substitution were on the stability and synthesis of mispairs between the unnatural and natural bases. Certain heteroatom substitutions were found to have a general effect while others were found to have effects that were specific for a particular unnatural or natural base. The data are useful for designing stable and replicable third base pairs and for understanding the contributions of nucleobase shape, polarity, and polarizability to the stability and replication of DNA.

  DOI：

  10.1021/ja035398o
• 作为产物：
  描述：

  6-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6H-thieno[2,3-c]pyridin-7-one 在 三氯乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 6-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-6H-thieno[2,3-c]pyridin-7-one
  参考文献：
  名称：

  Determinants of Unnatural Nucleobase Stability and Polymerase Recognition

  摘要：

  Six new unnatural nucleobases have been synthesized and characterized in terms of stability and selectivity of self-pairing in duplex DNA and efficiency and fidelity of self-pairing during polymerase-mediated replication. Each nucleobase has a conserved ring structure but differs from the others in its specific pattern of substitution with oxygen and sulfur atoms. Heteroatom derivatization within the conserved scaffold is shown to have only moderate effects on unnatural self-pair synthesis by the polymerase; larger effects were observed on the thermal stability and polymerase-mediated extension of the self-pairs. The largest effects of heteroatom substitution were on the stability and synthesis of mispairs between the unnatural and natural bases. Certain heteroatom substitutions were found to have a general effect while others were found to have effects that were specific for a particular unnatural or natural base. The data are useful for designing stable and replicable third base pairs and for understanding the contributions of nucleobase shape, polarity, and polarizability to the stability and replication of DNA.

  DOI：

  10.1021/ja035398o