(S)-1-((4R,5S)-5-((1R,4R)-1-acetoxy-4-hydroxyhept-6-en-2-ynyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl acetate | 1614220-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-1-((4R,5S)-5-((1R,4R)-1-acetoxy-4-hydroxyhept-6-en-2-ynyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl acetate
• CAS: 1614220-23-3
• 化学式: C₁₈H₂₆O₇
• 分子量: 354.4
• InChiKey: BGNVHEKVGBYUNI-PAZMTAOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.33
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-1-((4R,5S)-5-((1R,4R)-1-acetoxy-4-hydroxyhept-6-en-2-ynyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl acetate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (1S)-1-((4R,5S)-5-((1R)-1-acetoxy-3-(6-oxo-3,6-dihydro-2H-pyran-2-yl)prop-2-ynyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl acetate
  参考文献：
  名称：

  Total synthesis of (−)-synrotolide and the evaluation of its antiproliferative activity

  摘要：

  The stereoselective synthesis of (-)-synrotolide was achieved in high overall yield from D-(-)-ribose and 3-butyn-1-ol. The pivotal step in this approach is the selective deprotection of the acetonide group in the presence of acetate groups using TiCl4. Moreover, the biological activity of (-)-synrotolide was evaluated on HeLa, PANC 1, HepG2, and SK-N-SH cancer cell lines. The (-)-synrotolide selectively and potently inhibited the growth of PANC 1 cell line. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.04.010
• 作为产物：
  描述：

  (S)-1-((4R,5S)-5-((1R,4R)-1-acetoxy-4-(tert-butyldimethylsilyloxy)hept-6-en-2-ynyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl acetate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以96%的产率得到(S)-1-((4R,5S)-5-((1R,4R)-1-acetoxy-4-hydroxyhept-6-en-2-ynyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl acetate
  参考文献：
  名称：

  Total synthesis of (−)-synrotolide and the evaluation of its antiproliferative activity

  摘要：

  The stereoselective synthesis of (-)-synrotolide was achieved in high overall yield from D-(-)-ribose and 3-butyn-1-ol. The pivotal step in this approach is the selective deprotection of the acetonide group in the presence of acetate groups using TiCl4. Moreover, the biological activity of (-)-synrotolide was evaluated on HeLa, PANC 1, HepG2, and SK-N-SH cancer cell lines. The (-)-synrotolide selectively and potently inhibited the growth of PANC 1 cell line. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.04.010