(2R,3R,4S)-2-((S)-((2R,4S,5S,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(4-iodobutyl)-2-methoxy-5-methyltetrahydro-2H-pyran-2-yl)((triethylsilyl)oxy)methyl)-3-methyl-3,4-dihydro-2H-pyran-4-ol | 1326243-70-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,4S)-2-((S)-((2R,4S,5S,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(4-iodobutyl)-2-methoxy-5-methyltetrahydro-2H-pyran-2-yl)((triethylsilyl)oxy)methyl)-3-methyl-3,4-dihydro-2H-pyran-4-ol
• CAS: 1326243-70-2
• 化学式: C₃₀H₅₉IO₆Si₂
• 分子量: 698.87
• InChiKey: DBBWIBCQEKKXHY-KVSPNNCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.05
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S)-2-((S)-((2R,4S,5S,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(4-iodobutyl)-2-methoxy-5-methyltetrahydro-2H-pyran-2-yl)((triethylsilyl)oxy)methyl)-3-methyl-3,4-dihydro-2H-pyran-4-ol 在 2,6-二甲基吡啶 、 lithium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 55.34h， 生成
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Diminutive Forms of (+)-Spongistatin 1: Lessons Learned

  摘要：

  The design, synthesis, and biological evaluation of two diminutive forms of (+)-spongistatin 1, in conjunction with the development of a potentially general design strategy to simplify highly flexible macrocyclic molecules while maintaining biological activity, have been achieved. Examination of the solution conformations of (+)-spongistatin 1 revealed a common conformational preference along the western perimeter comprising the ABEF rings. Exploiting the hypothesis that the small-molecule recognition/binding domains are likely to comprise the conformationally less mobile portions of a ligand led to the design of analogues, incorporating tethers (blue) in place of the CD and the ABCD components of the (+)-spongistatin 1 macrolide, such that the conformation of the retained (+)-spongistatin 1 skeleton would mimic the assigned solution conformations of the natural product. The observed nanomolar cytotoxicity and microtubule destabilizing activity of the ABEF analogue provide support for both the assigned solution conformation of (+)-spongistatin 1 and the validity of the design strategy.

  DOI：

  10.1021/ja2046167
• 作为产物：
  描述：

  在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 4,4'-二叔丁基苯并 、 sodium hexamethyldisilazane 、 lithium 、 三乙胺 、 lithium iodide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 二氯甲烷 、 乙腈 为溶剂， 反应 87.5h， 生成 (2R,3R,4S)-2-((S)-((2R,4S,5S,6R)-4-((tert-butyldimethylsilyl)oxy)-6-(4-iodobutyl)-2-methoxy-5-methyltetrahydro-2H-pyran-2-yl)((triethylsilyl)oxy)methyl)-3-methyl-3,4-dihydro-2H-pyran-4-ol
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Diminutive Forms of (+)-Spongistatin 1: Lessons Learned

  摘要：

  The design, synthesis, and biological evaluation of two diminutive forms of (+)-spongistatin 1, in conjunction with the development of a potentially general design strategy to simplify highly flexible macrocyclic molecules while maintaining biological activity, have been achieved. Examination of the solution conformations of (+)-spongistatin 1 revealed a common conformational preference along the western perimeter comprising the ABEF rings. Exploiting the hypothesis that the small-molecule recognition/binding domains are likely to comprise the conformationally less mobile portions of a ligand led to the design of analogues, incorporating tethers (blue) in place of the CD and the ABCD components of the (+)-spongistatin 1 macrolide, such that the conformation of the retained (+)-spongistatin 1 skeleton would mimic the assigned solution conformations of the natural product. The observed nanomolar cytotoxicity and microtubule destabilizing activity of the ABEF analogue provide support for both the assigned solution conformation of (+)-spongistatin 1 and the validity of the design strategy.

  DOI：

  10.1021/ja2046167