1-(2,3:5,6-di-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)uracil | 1454611-72-3

• 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: 1-(2,3:5,6-di-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)uracil
• CAS: 1454611-72-3
• 化学式: C₁₆H₂₂N₂O₇
• 分子量: 354.36
• InChiKey: CQVYAXQXTBVDJX-JOLIMNQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.11
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  101.01
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  1-(2,3:5,6-di-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)uracil 在 吡啶 、 4-二甲氨基吡啶 、 三甲基氯硅烷 、 水 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 11.5h， 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
• 作为产物：
  描述：

  1-(2,3,5,6-tetra-O-acetyl-α,β-D-ribo-(5R)-hexofuranosyl)uracil 、 2,2-二甲氧基丙烷 在 氨 、 对甲苯磺酸 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 5.0h， 以77%的产率得到1-(2,3:5,6-di-O-isopropylidene-β-D-ribo-(5R)-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