(2S)-2-[(1S)-1-phenylmethoxyethyl]-2,3-dihydropyran-4-one | 1076236-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S)-2-[(1S)-1-phenylmethoxyethyl]-2,3-dihydropyran-4-one
• CAS: 1076236-57-1
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: ZXBCHTNZIQARCC-FZMZJTMJSA-N

物化性质

• 沸点：
  333.6±11.0 °C(predicted)
• 密度：
  1.124±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(1S)-1-phenylmethoxyethyl]-2,3-dihydropyran-4-one 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以96%的产率得到(2S,4S)-2-[(1S)-1-phenylmethoxyethyl]-3,4-dihydro-2H-pyran-4-ol
  参考文献：
  名称：

  Pre-mRNA Splicing-Modulatory Pharmacophores: The Total Synthesis of Herboxidiene, a Pladienolide–Herboxidiene Hybrid Analog and Related Derivatives

  摘要：

  Herboxidiene is a natural product that has previously been shown to exhibit antitumor activity by targeting the spliceosome. This activity makes herboxidiene a valuable starting point for the development of anticancer drugs. Here, we report an improved enantioselective synthesis of herboxidiene and the first report of its biologically active totally synthetic analog: 6-norherboxidiene. The synthesis of the tetrahydropyran moiety utilizes the novel application of inverse electron-demand Diels-Alder chemistry and the Ferrier-type rearrangement as key steps. We report, for the first time, cytotoxicity IC(50)s for synthetic herboxidiene and analogs in human tumor cell lines. We have also demonstrated that synthetic herboxidiene and its analogs can potently modulate the alternate splicing of MDM-2 pre-mRNA.

  DOI：

  10.1021/cb400695j
• 作为产物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 (S)-2-苄氧基丙醛 在 magnesium bromide 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到(2S)-2-[(1S)-1-phenylmethoxyethyl]-2,3-dihydropyran-4-one
  参考文献：
  名称：

  Synthetic studies directed toward amphidinol 2: elucidation of the relative configuration of the C1–C10 fragment

  摘要：

  Model compounds (11 and 12) for the C1-C10 tetrahydropyran fragment of amphidinol 2 were prepared from (2S)-benzyloxypropanal in 9 steps. The synthetic route relied on diastereoselective diene-aldehyde cycloaddition, stereoselective C-allylation, and reagent based enantioselective aldehyde allylation. Comparison of the NMR spectra for models 11 and 12 with that for amphidinol 2 indicated that the C1-C10 segment of the natural product possesses the 2R*,4R*,6R*,7S*,8R*,10S* relative configuration. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.035

文献信息

• Synthetic studies directed toward amphidinol 2: elucidation of the relative configuration of the C1–C10 fragment
  作者：Praveen Kommana、Seung Won Chung、William A. Donaldson

  DOI：10.1016/j.tetlet.2008.08.035

  日期：2008.10

  Model compounds (11 and 12) for the C1-C10 tetrahydropyran fragment of amphidinol 2 were prepared from (2S)-benzyloxypropanal in 9 steps. The synthetic route relied on diastereoselective diene-aldehyde cycloaddition, stereoselective C-allylation, and reagent based enantioselective aldehyde allylation. Comparison of the NMR spectra for models 11 and 12 with that for amphidinol 2 indicated that the C1-C10 segment of the natural product possesses the 2R*,4R*,6R*,7S*,8R*,10S* relative configuration. (C) 2008 Elsevier Ltd. All rights reserved.
• Pre-mRNA Splicing-Modulatory Pharmacophores: The Total Synthesis of Herboxidiene, a Pladienolide–Herboxidiene Hybrid Analog and Related Derivatives
  作者：Chandraiah Lagisetti、Maria V. Yermolina、Lalit Kumar Sharma、Gustavo Palacios、Brett J. Prigaro、Thomas R. Webb

  DOI：10.1021/cb400695j

  日期：2014.3.21

  Herboxidiene is a natural product that has previously been shown to exhibit antitumor activity by targeting the spliceosome. This activity makes herboxidiene a valuable starting point for the development of anticancer drugs. Here, we report an improved enantioselective synthesis of herboxidiene and the first report of its biologically active totally synthetic analog: 6-norherboxidiene. The synthesis of the tetrahydropyran moiety utilizes the novel application of inverse electron-demand Diels-Alder chemistry and the Ferrier-type rearrangement as key steps. We report, for the first time, cytotoxicity IC(50)s for synthetic herboxidiene and analogs in human tumor cell lines. We have also demonstrated that synthetic herboxidiene and its analogs can potently modulate the alternate splicing of MDM-2 pre-mRNA.