methyl 5-deoxy-5-{2,4-dioxo-5-[(2-trimethylsilyl)ethynyl]pyrimidin-1H-1-yl}-2,3-O-isopropylidene-β-D-ribofuranoside | 168696-06-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: methyl 5-deoxy-5-{2,4-dioxo-5-[(2-trimethylsilyl)ethynyl]pyrimidin-1H-1-yl}-2,3-O-isopropylidene-β-D-ribofuranoside
• CAS: 168696-06-8
• 化学式: C₁₈H₂₆N₂O₆Si
• 分子量: 394.5
• InChiKey: RIRLRDJUZYUCOF-IXYNUQLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  91.78
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 5-deoxy-5-{2,4-dioxo-5-[(2-trimethylsilyl)ethynyl]pyrimidin-1H-1-yl}-2,3-O-isopropylidene-β-D-ribofuranoside 在 Amberlite IR-120(H⁺) 作用下， 以 甲醇 为溶剂， 以78%的产率得到methyl 5-deoxy-5-(2,4-dioxo-5-acetylpyrimidin-1H-1-yl)-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis of "Reversed" and "Double Headed" Nucleosides

  摘要：

  The synthesis of several partially and fully deprotected ''reversed'' nucleosides are described starting from ''reversed'' 5-iodouracil-1-yl nucleoside 1. The preparation of a novel purine-purine and mixed purine-pyrimidine ''double headed'' nucleosides via ''reversed'' purine nucleoside 12 is also described.

  DOI：

  10.1080/15257779508012377
• 作为产物：
  描述：

  methyl 5-deoxy-5-(2,4-dioxo-5-iodopyrimidin-1H-1-yl)-2,3-O-isopropylidene-β-D-ribofuranoside 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 8.0h， 以71%的产率得到methyl 5-deoxy-5-{2,4-dioxo-5-[(2-trimethylsilyl)ethynyl]pyrimidin-1H-1-yl}-2,3-O-isopropylidene-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis and Biological Activity of Reversed Pyrimidine Nucleosides

  摘要：

  An efficient approach to reversed nucleosides which enables their synthesis in gram quantities is described. N-1'-Pyrimidine reversed nucleosides were prepared by treating of the sodium salt of pyrimidine bases with protected 5-tosyl ribose. Additionally, N-1',N-3'-disubstituted reversed nucleosides were isolated in the condensation reactions with the 5-halogen pyrimidines. Using the Sonogashira coupling of 5'-iodouracil reversed nucleoside with ethynyltrimethyl silane gave 5'-ethynyl derivative which was further transformed into 5'-acetyl reversed nucleoside. Biological activity of deprotected reversed nucleosides was validated on the panel of six human carcinoma cell lines (HeLa, MIAPaCa2, Hep2, NCI-H358, CaCo-2, and HT-29). 5'-Iodouracil derivative displayed moderate growth inhibition activity against human colon carcinoma (CaCo-2) cells.

  DOI：

  10.5562/cca2531