9-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)-6-O-methylpurine | 1454611-98-3

• 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: 9-(2,3-O-isopropylidene-β-D-ribo-(5R)-hexofuranosyl)-6-O-methylpurine
• CAS: 1454611-98-3
• 化学式: C₁₅H₂₀N₄O₆
• 分子量: 352.347
• InChiKey: VTQOUEFLPBBFAU-RDROLGDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.39
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  120.98
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  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76%的产率得到9-(2,3-O-isopropylidene-5,6-oxiran-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：

  9-(2,3,5,6-tetra-O-acetyl-β-D-ribo-(5R)-hexofuranosyl)-6-chloropurine 在 水 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 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