9-((3aR,4R,6R,6aS)-4-(tert-butoxymethyl)-2,2-dimethyltetrahydrospiro[cyclopenta[d][1,3]dioxole-5,1'-cyclopropan]-6-yl)-6-chloro-9H-purine | 1314254-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-((3aR,4R,6R,6aS)-4-(tert-butoxymethyl)-2,2-dimethyltetrahydrospiro[cyclopenta[d][1,3]dioxole-5,1'-cyclopropan]-6-yl)-6-chloro-9H-purine
• CAS: 1314254-55-1
• 化学式: C₂₀H₂₇ClN₄O₃
• 分子量: 406.912
• InChiKey: HRJBPPSFUNRZAQ-NGFQHRJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  71.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  9-((3aR,4R,6R,6aS)-4-(tert-butoxymethyl)-2,2-dimethyltetrahydrospiro[cyclopenta[d][1,3]dioxole-5,1'-cyclopropan]-6-yl)-6-chloro-9H-purine 在 diazenedicarboxylic acid 、 氨 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 11.0h， 生成 (4R,5S,6R,7R)-4-(6-amino-9H-purin-9-yl)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol
  参考文献：
  名称：

  Synthesis and antiviral activity of cyclopropyl-spirocarbocyclic adenosine, (4 R ,5 S ,6 R ,7 R )-4-(6-amino-9 H -purin-9-yl)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol against hepatitis C virus

  摘要：

  An efficient method was developed for the synthesis of 6-exocyclic methylene carbocyclic intermediate 4. The Simmons-Smith cyclopropanation protocol was applied on the 6-exocyclic methylene of intermediate 4 and demonstrated its utility for the synthesis of novel class of a spiro-carbocyclic nucleoside analog 8. The titled compound 8 demonstrated a significant antiviral activity against HCV with EC(50) values of 0.273 and 0.368 mu M in genotypes 1A and 1B, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.012
• 作为产物：
  描述：

  (3R,6R,6aR)-6-(tert-butoxymethyl)-2,2-dimethyl-5-methylenedihydro-3aH-cyclopenta[d][1,3]-dioxol-4-(5H)one 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 偶氮二甲酸二异丙酯 、 diethylzinc 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 8.5h， 生成 9-((3aR,4R,6R,6aS)-4-(tert-butoxymethyl)-2,2-dimethyltetrahydrospiro[cyclopenta[d][1,3]dioxole-5,1'-cyclopropan]-6-yl)-6-chloro-9H-purine
  参考文献：
  名称：

  Synthesis and antiviral activity of cyclopropyl-spirocarbocyclic adenosine, (4 R ,5 S ,6 R ,7 R )-4-(6-amino-9 H -purin-9-yl)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol against hepatitis C virus

  摘要：

  An efficient method was developed for the synthesis of 6-exocyclic methylene carbocyclic intermediate 4. The Simmons-Smith cyclopropanation protocol was applied on the 6-exocyclic methylene of intermediate 4 and demonstrated its utility for the synthesis of novel class of a spiro-carbocyclic nucleoside analog 8. The titled compound 8 demonstrated a significant antiviral activity against HCV with EC(50) values of 0.273 and 0.368 mu M in genotypes 1A and 1B, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.012