<7-¹⁵N>-6-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine

• 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: <7-¹⁵N>-6-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine
• 英文别名: [7-¹⁵N]-6-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine；(2R,3S,5R)-5-(6-chloropurin-9-yl)-2-(hydroxymethyl)oxolan-3-ol
• 化学式: C₁₀H₁₁ClN₄O₃
• 分子量: 271.669
• InChiKey: PGEULCIODBNODW-XRWBCCKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <7-¹⁵N>-6-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine 在 ¹⁵N-ammonium chloride 、 potassium hydrogencarbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以90%的产率得到[6,7-¹⁵N]-2'-deoxyadenosine
  参考文献：
  名称：

  Syntheses of [6,7-15N]-Adenosine, [6,7-15N]-2'-Deoxyadenosine, and [7-15N]-Hypoxanthine

  摘要：

  We have developed a high-yield route for the synthesis of [7-N-15]-hypoxanthine in four steps in an overall yield of 81%. This procedure uses [N-15]-sodium nitrite as the N-15 source and an inexpensive pyrimidine to provide an economical route to this useful N-15-labeled intermediate. Conversion to [7-N-15]-6-chloropurine followed by enzymatic transglycosylation gives the corresponding ribo- and 2'-deoxyribonucleosides. Ammonolysis of the 6-chloro moiety to give the [6,7-N-15]-labeled nucleosides is effected simply and in high yield using 2 equiv of [N-15]-ammonium chloride and 3 equiv of potassium bicarbonate.

  DOI：

  10.1021/ja00152a006
• 作为产物：
  描述：

  <7-¹⁵N>-6-chloropurine 、 beta-胸苷 在 dipotassium hydrogenphosphate 作用下， 反应 48.0h， 以86%的产率得到<7-¹⁵N>-6-chloro-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine
  参考文献：
  名称：

  Syntheses of [6,7-15N]-Adenosine, [6,7-15N]-2'-Deoxyadenosine, and [7-15N]-Hypoxanthine

  摘要：

  We have developed a high-yield route for the synthesis of [7-N-15]-hypoxanthine in four steps in an overall yield of 81%. This procedure uses [N-15]-sodium nitrite as the N-15 source and an inexpensive pyrimidine to provide an economical route to this useful N-15-labeled intermediate. Conversion to [7-N-15]-6-chloropurine followed by enzymatic transglycosylation gives the corresponding ribo- and 2'-deoxyribonucleosides. Ammonolysis of the 6-chloro moiety to give the [6,7-N-15]-labeled nucleosides is effected simply and in high yield using 2 equiv of [N-15]-ammonium chloride and 3 equiv of potassium bicarbonate.

  DOI：

  10.1021/ja00152a006

文献信息

• Syntheses of [6,7-15N]-Adenosine, [6,7-15N]-2'-Deoxyadenosine, and [7-15N]-Hypoxanthine
  作者：Alex R. Pagano、Wayne M. Lajewski、Roger A. Jones

  DOI：10.1021/ja00152a006

  日期：1995.11

  We have developed a high-yield route for the synthesis of [7-N-15]-hypoxanthine in four steps in an overall yield of 81%. This procedure uses [N-15]-sodium nitrite as the N-15 source and an inexpensive pyrimidine to provide an economical route to this useful N-15-labeled intermediate. Conversion to [7-N-15]-6-chloropurine followed by enzymatic transglycosylation gives the corresponding ribo- and 2'-deoxyribonucleosides. Ammonolysis of the 6-chloro moiety to give the [6,7-N-15]-labeled nucleosides is effected simply and in high yield using 2 equiv of [N-15]-ammonium chloride and 3 equiv of potassium bicarbonate.