[(2S)-2-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]-2-hydroxyethyl]phosphonic acid | 934461-13-9

• 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: [(2S)-2-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]-2-hydroxyethyl]phosphonic acid
• CAS: 934461-13-9
• 化学式: C₁₁H₁₅N₄O₈P
• 分子量: 362.236
• InChiKey: UDOMZKQGLMSEJL-RWONEVQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  187
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2S)-2-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]-2-hydroxyethyl]phosphonic acid 、 alkaline earth salt of/the/ methylsulfuric acid 以59 mg的产率得到9-(5S)-[6-deoxy-6-phosphono-β-D-ribohexofuranosyl]hypoxanthine disodium salt
  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-penta-O-acetyl-(α,β)-D-allofuranose 在 甲酸 、 N,O-双三甲硅基乙酰胺 、 三甲基溴硅烷 、 水 、 四氯化锡 、 potassium carbonate 、 对甲苯磺酸 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 12.0h， 生成 [(2S)-2-[(2S,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]-2-hydroxyethyl]phosphonic acid
  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.