2-amino-9-(2,3:5,6-di-O-isopropylidene-β-D-ribo-(5’R)-hexofuranosyl)-6-O-methylpurine | 1454611-96-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-amino-9-(2,3:5,6-di-O-isopropylidene-β-D-ribo-(5’R)-hexofuranosyl)-6-O-methylpurine
• CAS: 1454611-96-1
• 化学式: C₁₈H₂₅N₅O₆
• 分子量: 407.426
• InChiKey: BDXXZCKYAXCKCO-NZIXVDBUSA-N

物化性质

• 沸点：
  613.1±65.0 °C(predicted)
• 密度：
  1.65±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  29.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  125.0
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2-amino-9-(2,3:5,6-di-O-isopropylidene-β-D-ribo-(5’R)-hexofuranosyl)-6-O-methylpurine 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 N,N-2(ditert-butoxycarbonyl)-9-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)-6-O-methylpurine
  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：

  2-amino-9-[(5’R)-(α,β)-hexofuranosyl]-6-chloropurine 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 2-amino-9-(2,3:5,6-di-O-isopropylidene-β-D-ribo-(5’R)-hexofuranosyl)-6-O-methylpurine
  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