N,N-2(ditert-butoxycarbonyl)-9-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuran-osyl)-6-O-methylpurine | 1454611-79-0

• 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: N,N-2(ditert-butoxycarbonyl)-9-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuran-osyl)-6-O-methylpurine
• CAS: 1454611-79-0
• 化学式: C₂₅H₃₅N₅O₉
• 分子量: 549.581
• InChiKey: XWBHTUOBZJQWBF-IPPHREHXSA-N

物化性质

• 沸点：
  651.7±65.0 °C(predicted)
• 密度：
  1.46±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  39.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  148.89
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N,N-2(ditert-butoxycarbonyl)-9-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuran-osyl)-6-O-methylpurine 在 N,O-双三甲硅基乙酰胺 、 三甲基溴硅烷 、 水 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成
  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：

  N,N-2(ditert-butoxycarbonyl)-9-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)-6-O-methylpurine 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以57%的产率得到N,N-2(ditert-butoxycarbonyl)-9-(2,3-O-isopropylidene-5,6-oxiran-β-D-ribo-(5R)-hexofuran-osyl)-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