1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-β-D-ribo-(5S)-hexofuranosyl)uracil | 1454611-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-β-D-ribo-(5S)-hexofuranosyl)uracil
• 英文别名: S-[2-[2-benzoylsulfanylethoxy-[(2S)-2-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl]-oxidophosphaniumyl]oxyethyl] benzenecarbothioate
• CAS: 1454611-87-0
• 化学式: C₂₈H₃₁N₂O₁₁PS₂
• 分子量: 666.667
• InChiKey: XQVMGGNVSWFEBY-AZCRNNOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  44
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  246
• 氢给体数：
  4
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  硫代苯甲酸 S-羟乙基酯 在 三甲基氯硅烷 、 三乙胺 、 三氟乙酸 、 三氯化磷 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 9.0h， 生成 1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-β-D-ribo-(5S)-hexofuranosyl)uracil
  参考文献：
  名称：

  An Alternative Pathway to Ribonucleoside β-Hydroxyphosphonate Analogues and Related Prodrugs

  摘要：

  Nucleoside beta-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5'-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of beta-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.

  DOI：

  10.1021/ol402143y

文献信息

• An Alternative Pathway to Ribonucleoside β-Hydroxyphosphonate Analogues and Related Prodrugs
  作者：Audrey Hospital、Maïa Meurillon、Suzanne Peyrottes、Christian Périgaud

  DOI：10.1021/ol402143y

  日期：2013.9.20

  Nucleoside beta-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5'-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of beta-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.