(2S,3S,4R)-2-((S)-1-(benzyloxy)ethyl)-3-methyl-3,4-dihydro-2H-pyran-4-yl acetate | 1528700-66-4

• 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,3S,4R)-2-((S)-1-(benzyloxy)ethyl)-3-methyl-3,4-dihydro-2H-pyran-4-yl acetate
• CAS: 1528700-66-4
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: OBHXUQXBPPNQOM-CLROSIBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.07
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-2-((S)-1-(benzyloxy)ethyl)-3-methyl-3,4-dihydro-2H-pyran-4-yl acetate 、 1-(叔丁基二甲基硅氧基)-1-甲氧基乙烯 在 二异丙氧基二氯化钛 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以33.333%的产率得到
  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：

  在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2S,3S,4R)-2-((S)-1-(benzyloxy)ethyl)-3-methyl-3,4-dihydro-2H-pyran-4-yl acetate
  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