(2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate | 1611470-13-3

• 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: (2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate
• CAS: 1611470-13-3
• 化学式: C₆₂H₆₀O₁₁
• 分子量: 981.152
• InChiKey: ALAXAMOBZOWACO-YMFBYMNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.77
• 重原子数：
  73.0
• 可旋转键数：
  21.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  125.05
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate 在 乙酸肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以72%的产率得到(2R,3R,4S,5R)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-hydroxytetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  Total synthesis of fuzinoside

  摘要：

  The first total syntheses of fuzinoside (1b) were achieved from o-galactose through two strategies (BCA and ABC) in 11 (total yield: 5.0%) and 15 (total yield: 3.7%) steps, respectively. Comparison of NMR data of synthetic compound 1b and those of the fuzinoside isolated from the lateral roots of Aconitum carmicaelii suggests that the structure reported in the literature(1,2) might not be accurate. The synthetic fuzinoside (1b) exhibited moderate cardiac activity in the isolated bullfrog heart assay. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.069
• 作为产物：
  描述：

  (2R,3S,4R,5S)-4-(tert-butyldiphenylsilyloxy)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-(p-tolylthio)tetrahydrofuran-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.5h， 生成 (2R,3R,4S,5S)-2-(1,3-bis(trityloxy)propan-2-yloxy)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(4-oxopentanoyloxy)tetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  Total synthesis of fuzinoside

  摘要：

  The first total syntheses of fuzinoside (1b) were achieved from o-galactose through two strategies (BCA and ABC) in 11 (total yield: 5.0%) and 15 (total yield: 3.7%) steps, respectively. Comparison of NMR data of synthetic compound 1b and those of the fuzinoside isolated from the lateral roots of Aconitum carmicaelii suggests that the structure reported in the literature(1,2) might not be accurate. The synthetic fuzinoside (1b) exhibited moderate cardiac activity in the isolated bullfrog heart assay. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.069