N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil | 1454611-85-8

• 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: N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil
• 英文别名: tert-butyl 3-[(3aR,4R,6R,6aR)-6-[(1S)-2-[bis(2-benzoylsulfanylethoxy)-oxidophosphaniumyl]-1-hydroxyethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2,6-dioxopyrimidine-1-carboxylate
• CAS: 1454611-85-8
• 化学式: C₃₆H₄₃N₂O₁₃PS₂
• 分子量: 806.849
• InChiKey: JDLUDYCMNRVWQE-VDFIJDOYSA-N

物化性质

• 沸点：
  849.5±75.0 °C(predicted)
• 密度：
  1.376±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  54
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  241
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)uracil 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以47%的产率得到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
• 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 、 三氯化磷 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 3.0h， 生成 N-3-tert-butoxycarbonyl-1-(6-deoxy-6-di(S-benzoylthio)ethylphosphono-2,3-O-isopropylidene-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.