9-(2,3,5,6-tetra-O-acetyl-β-D-ribo-(5R)-hexofuranosyl)-6-chloropurine | 1261280-73-2

• 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-(2,3,5,6-tetra-O-acetyl-β-D-ribo-(5R)-hexofuranosyl)-6-chloropurine
• 英文别名: [(2R)-2-acetyloxy-2-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(6-chloropurin-9-yl)oxolan-2-yl]ethyl] acetate
• CAS: 1261280-73-2
• 化学式: C₁₉H₂₁ClN₄O₉
• 分子量: 484.85
• InChiKey: XPYJYSAKAXTIHZ-IPPHREHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  158
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  9-(2,3,5,6-tetra-O-acetyl-β-D-ribo-(5R)-hexofuranosyl)-6-chloropurine 在 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 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
• 作为产物：
  描述：

  6-氯嘌呤 、 1,2,3,5,6-penta-O-acetyl-(α,β)-D-allofuranose 在 四氯化锡 作用下， 以 乙腈 为溶剂， 以80%的产率得到9-(2,3,5,6-tetra-O-acetyl-β-D-ribo-(5R)-hexofuranosyl)-6-chloropurine
  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.