[(6aR,8R,9R,9aR)-8-(2-amino-6-chloropurin-9-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl]oxy-phenoxymethanethione | 170872-60-3

• 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: [(6aR,8R,9R,9aR)-8-(2-amino-6-chloropurin-9-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl]oxy-phenoxymethanethione
• CAS: 170872-60-3
• 化学式: C₂₉H₄₂ClN₅O₆SSi₂
• 分子量: 680.372
• InChiKey: ICGRNWMBKFGQKA-VBHAUSMQSA-N

物化性质

• 沸点：
  691.3±65.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.66
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  157
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(6aR,8R,9R,9aR)-8-(2-amino-6-chloropurin-9-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl]oxy-phenoxymethanethione 在 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 苯 为溶剂， 反应 5.17h， 生成 2-amino-9-(2-deoxy-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  A New Approach to the Synthesis of 2-Aminopurine-2′-deoxyribosideviaTri-n-butyltin Hydride Reduction

  摘要：

  A simple conversion of guanosine to 2-aminopurine-2'-deoxyriboside is described. Following the synthesis of the 2'-phenoxythiocarbonyl derivative of 6-chloroguanosine, 2-aminopurine-2'-deoxyriboside can be prepared by simultaneous reduction of both the 6- and 2'-position using tri-n-butyltin hydride as reducing agent. Several oligonucleotides containing 2-aminopurine-2'-deoxyriboside have been synthesized.

  DOI：

  10.1080/15257779508010704
• 作为产物：
  描述：

  6-氯鸟嘌呤核苷 在 4-二甲氨基吡啶 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.0h， 生成 [(6aR,8R,9R,9aR)-8-(2-amino-6-chloropurin-9-yl)-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-yl]oxy-phenoxymethanethione
  参考文献：
  名称：

  A New Approach to the Synthesis of 2-Aminopurine-2′-deoxyribosideviaTri-n-butyltin Hydride Reduction

  摘要：

  A simple conversion of guanosine to 2-aminopurine-2'-deoxyriboside is described. Following the synthesis of the 2'-phenoxythiocarbonyl derivative of 6-chloroguanosine, 2-aminopurine-2'-deoxyriboside can be prepared by simultaneous reduction of both the 6- and 2'-position using tri-n-butyltin hydride as reducing agent. Several oligonucleotides containing 2-aminopurine-2'-deoxyriboside have been synthesized.

  DOI：

  10.1080/15257779508010704

文献信息

• A New Approach to the Synthesis of 2-Aminopurine-2′-deoxyriboside<i>via</i>Tri-n-butyltin Hydride Reduction
  作者：Sabine Schmidt、Dieter Cech

  DOI：10.1080/15257779508010704

  日期：1995.8

  A simple conversion of guanosine to 2-aminopurine-2'-deoxyriboside is described. Following the synthesis of the 2'-phenoxythiocarbonyl derivative of 6-chloroguanosine, 2-aminopurine-2'-deoxyriboside can be prepared by simultaneous reduction of both the 6- and 2'-position using tri-n-butyltin hydride as reducing agent. Several oligonucleotides containing 2-aminopurine-2'-deoxyriboside have been synthesized.