(2S)-2-[[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]oxolan-2-yl]methyl]-4-methyl-2,3-dihydropyran-6-one | 1279710-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S)-2-[[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]oxolan-2-yl]methyl]-4-methyl-2,3-dihydropyran-6-one
• CAS: 1279710-15-4
• 化学式: C₂₂H₃₈O₄Si
• 分子量: 394.627
• InChiKey: KDLCJSJORDFKCO-IYWMVGAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2S)-1-[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]oxolan-2-yl]-4-methylpent-4-en-2-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2S)-2-[[(2R,5R)-5-[(1R)-1-[tert-butyl(dimethyl)silyl]oxy-3-methylbut-2-enyl]oxolan-2-yl]methyl]-4-methyl-2,3-dihydropyran-6-one
  参考文献：
  名称：

  Synthesis of the C22–C37 segment of prorocentin

  摘要：

  The synthesis of the C22-C37 segment of prorocentin, isolated from the dinoflagellate Prorocentrum lima, was achieved. Because the relative stereochemical relationship between C26 and other stereocenters (C28/C31/C32 established as R*/R*/R*) in the C22-C37 region of natural prorocentin has not yet been determined, both epimers at C26 of the C22-C37 segment were selectively constructed. The synthesis was based on a 5-exo epoxide ring opening reaction to form an oxolane (E-ring). Brown asymmetric methallylation to install the C26-stereocenter, acryloylation of the resulting alcohol, and ring-closing olefin metathesis to establish the Z-olefin at C23/C24. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.042

文献信息

• Synthesis of the C22–C37 segment of prorocentin
  作者：Atsushi Takemura、Yasushi Katagiri、Kenshu Fujiwara、Hidetoshi Kawai、Takanori Suzuki

  DOI：10.1016/j.tetlet.2011.01.042

  日期：2011.3

  The synthesis of the C22-C37 segment of prorocentin, isolated from the dinoflagellate Prorocentrum lima, was achieved. Because the relative stereochemical relationship between C26 and other stereocenters (C28/C31/C32 established as R*/R*/R*) in the C22-C37 region of natural prorocentin has not yet been determined, both epimers at C26 of the C22-C37 segment were selectively constructed. The synthesis was based on a 5-exo epoxide ring opening reaction to form an oxolane (E-ring). Brown asymmetric methallylation to install the C26-stereocenter, acryloylation of the resulting alcohol, and ring-closing olefin metathesis to establish the Z-olefin at C23/C24. (C) 2011 Elsevier Ltd. All rights reserved.