2-iodo-6-methoxy-9-(2-O-acetyl-β-D-arabinofuranosyl)purine | 157762-22-6

• 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: 2-iodo-6-methoxy-9-(2-O-acetyl-β-D-arabinofuranosyl)purine
• CAS: 157762-22-6
• 化学式: C₁₃H₁₅IN₄O₆
• 分子量: 450.19
• InChiKey: FZVADAAZPMAKHB-QRKAXHLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.38
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  128.82
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-iodo-6-methoxy-9-(2-O-acetyl-β-D-arabinofuranosyl)purine 在 氨 、 对甲苯磺酸 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-iodo-6-methoxy-9-(2-deoxy-2-fluoro-3,5-di-O-(tetrahydro-2-pyranyl)-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 2-Substituted 2′-Deoxy-2′-fluoroadenosines

  摘要：

  2-Iodo-6-methoxypurine 2'-deoxy-2'-fluororiboside 8 was prepared from 2-iodo-6-methoxypurine riboside 1 in 8 steps. Reaction of 8 with ammonia in methanol gave the 2-iodoadenosine derivative 9 in 69% yield. Treatment of 9 with various nucleophiles gave 2-substituted analogues of 2'-deoxy-2'-fluoroadenosine 10-12. 2'-Deoxy-2,2'-difluoroadenosine 14 was also prepared by the treatment of the quaternary salt 13 with fluoride ion, but similar reactions of 13 with chloride or bromide ion gave the corresponding piperidine congeners 15a,b.

  DOI：

  10.1080/15257779408012146
• 作为产物：
  描述：

  2-iodo-6-methoxy-9-(2-O-acetyl-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl)purine 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以69%的产率得到2-iodo-6-methoxy-9-(2-O-acetyl-β-D-arabinofuranosyl)purine
  参考文献：
  名称：

  Synthesis and Anti-HIV Activity of 2-Substituted 2′-Deoxy-2′-fluoroadenosines

  摘要：

  2-Iodo-6-methoxypurine 2'-deoxy-2'-fluororiboside 8 was prepared from 2-iodo-6-methoxypurine riboside 1 in 8 steps. Reaction of 8 with ammonia in methanol gave the 2-iodoadenosine derivative 9 in 69% yield. Treatment of 9 with various nucleophiles gave 2-substituted analogues of 2'-deoxy-2'-fluoroadenosine 10-12. 2'-Deoxy-2,2'-difluoroadenosine 14 was also prepared by the treatment of the quaternary salt 13 with fluoride ion, but similar reactions of 13 with chloride or bromide ion gave the corresponding piperidine congeners 15a,b.

  DOI：

  10.1080/15257779408012146