ethyl 2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-3-methoxyacrylate | 925672-13-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: ethyl 2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-3-methoxyacrylate
• CAS: 925672-13-5
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: XNBAAUNJWDGZPD-NBZVVWIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-3-methoxyacrylate 在 盐酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 50.0h， 生成 5-[(1S,2R,3R)-2,3-dihydroxy-4-hydroxymethyl-4-cyclopenten-1-yl]uracil
  参考文献：
  名称：

  Enantioselective synthesis and antiviral activity of purine and pyrimidine cyclopentenyl C-nucleosides

  摘要：

  The enantiomerically pure carbocyclic purine and pyrimidine C-nucleosides 1-4 were synthesized via the key intermediate, 2,3-(isopropylidenedioxy)-4-(trityloxymethyl) -4-cyclopenten-1-ol (5), which was prepared from D-ribose in eight steps. Synthesized compounds were evaluated as potential antiviral agents against HIV, SARSCoV, Punta Toro, West Nile, and Cowpox viruses. However, only 9-deazaneplanocin A (1) exhibited moderate anti-HIV activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.043
• 作为产物：
  描述：

  (3AS,4S,6AR)-2,2-二甲基-6-((三苯甲基氧基)甲基)-4,6A二氢-3AH-环 在 水 、 sodium hydride 、 三乙胺 、 lithium chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 69.0h， 生成 ethyl 2-[(1S,2R,3R)-2,3-(isopropylidenedioxy)-4-(trityloxymethyl)-4-cyclopenten-1-yl]-3-methoxyacrylate
  参考文献：
  名称：

  Enantioselective synthesis and antiviral activity of purine and pyrimidine cyclopentenyl C-nucleosides

  摘要：

  The enantiomerically pure carbocyclic purine and pyrimidine C-nucleosides 1-4 were synthesized via the key intermediate, 2,3-(isopropylidenedioxy)-4-(trityloxymethyl) -4-cyclopenten-1-ol (5), which was prepared from D-ribose in eight steps. Synthesized compounds were evaluated as potential antiviral agents against HIV, SARSCoV, Punta Toro, West Nile, and Cowpox viruses. However, only 9-deazaneplanocin A (1) exhibited moderate anti-HIV activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.043