(3R,5S,2'R,6'S)-3-(2',6'-oxido-8'-oxo-9'-decenyl)-5-methyl-3-(phenylthio)tetrahydrofuran-2-one | 1064038-34-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (3R,5S,2'R,6'S)-3-(2',6'-oxido-8'-oxo-9'-decenyl)-5-methyl-3-(phenylthio)tetrahydrofuran-2-one
• 英文别名: (3R,5S)-5-methyl-3-[[(2R,6S)-6-(2-oxobut-3-enyl)oxan-2-yl]methyl]-3-phenylsulfanyloxolan-2-one
• CAS: 1064038-34-1
• 化学式: C₂₁H₂₆O₄S
• 分子量: 374.501
• InChiKey: FYVYBYBASWFZEV-DZKDUJFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  77.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,5S,2'R,6'S)-3-(2',6'-oxido-8'-oxo-9'-decenyl)-5-methyl-3-(phenylthio)tetrahydrofuran-2-one 、 (5R,6R,9R,10R)-5,10-di-(t-butyldimethylsilyloxy)-6,9-oxido-1-docosene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 以82%的产率得到(3R,5S,2'R,6'S,13'R,14'R,17'R,18'R)-[13',18'-di-(t-butyldimethylsilyloxy)-2',6':14',17'-dioxido-8'-oxo-9'-triacontenyl]-5-methyl-3-(phenylthio)tetrahydrofuran-2-one
  参考文献：
  名称：

  Structural Determination of Montanacin D by Total Synthesis

  摘要：

  The first total syntheses of acetogenin 3 and its 4S,8R-isomer are described. The key step involves intermolecular metathesis of an alpha,beta-unsaturated ketone carrying a tetra hydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of natural montanacin D, suggesting that the absolute configuration of the natural product is as shown in 3.

  DOI：

  10.1021/ol801576z
• 作为产物：
  描述：

  在 三氧化硫-三乙胺复合物 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 38.0h， 生成 (3R,5S,2'R,6'S)-3-(2',6'-oxido-8'-oxo-9'-decenyl)-5-methyl-3-(phenylthio)tetrahydrofuran-2-one 、 (3S,5S,2'R,6'S)-3-(2',6'-oxido-8'-oxo-9'-decenyl)-5-methyl-3-(phenylthio)tetrahydrofuran-2-one
  参考文献：
  名称：

  Structural Determination of Montanacin D by Total Synthesis

  摘要：

  The first total syntheses of acetogenin 3 and its 4S,8R-isomer are described. The key step involves intermolecular metathesis of an alpha,beta-unsaturated ketone carrying a tetra hydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of natural montanacin D, suggesting that the absolute configuration of the natural product is as shown in 3.

  DOI：

  10.1021/ol801576z

文献信息

• Structural Determination of Montanacin D by Total Synthesis
  作者：Shunya Takahashi、Yayoi Hongo、Yuki Tsukagoshi、Hiroyuki Koshino

  DOI：10.1021/ol801576z

  日期：2008.10.2

  The first total syntheses of acetogenin 3 and its 4S,8R-isomer are described. The key step involves intermolecular metathesis of an alpha,beta-unsaturated ketone carrying a tetra hydropyranyl lactone with a tetrahydrofuran derivative. Compound 3 has spectroscopic and physical data consistent with those of natural montanacin D, suggesting that the absolute configuration of the natural product is as shown in 3.