5-((1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethynyl)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl diacetate | 710326-63-9

• 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: 5-((1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethynyl)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl diacetate
• CAS: 710326-63-9
• 化学式: C₃₅H₂₆N₂O₁₂
• 分子量: 666.598
• InChiKey: RECPFMRJAJWWMS-LXLYTFERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.0
• 重原子数：
  49.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  192.68
• 氢给体数：
  3.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  5-((1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethynyl)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl diacetate 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 5-[1-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylethynyl]-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)-benzoic acid
  参考文献：
  名称：

  A Blue-to-Red Energy-Transfer Thymidine Analogue That Functions in DNA

  摘要：

  The thymidine analogue 1 is a blue-to-red energy transfer cassette designed to absorb UV light in the 300 nm region and emit it as fluorescence at around 520 nm. When incorporated into DNA, the fluorescence intensity of this modified nucleobase is not significantly reduced by the surrounding structure in the oligonucleotides.

  DOI：

  10.1021/ol049684w
• 作为产物：
  描述：

  5-((1-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethynyl)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl diacetate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以96%的产率得到5-((1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)ethynyl)-3-oxo-3H-spiro[isobenzofuran-1,9'-xanthene]-3',6'-diyl diacetate
  参考文献：
  名称：

  A Blue-to-Red Energy-Transfer Thymidine Analogue That Functions in DNA

  摘要：

  The thymidine analogue 1 is a blue-to-red energy transfer cassette designed to absorb UV light in the 300 nm region and emit it as fluorescence at around 520 nm. When incorporated into DNA, the fluorescence intensity of this modified nucleobase is not significantly reduced by the surrounding structure in the oligonucleotides.

  DOI：

  10.1021/ol049684w