3,7,11-tris[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9-[({[({5-[(2-propenyloxy)carbonyl]amino}hexyl)amino]carbonyl}oxy)pentyl]discodermolide | 184291-89-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3,7,11-tris[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9-[({[({5-[(2-propenyloxy)carbonyl]amino}hexyl)amino]carbonyl}oxy)pentyl]discodermolide
• CAS: 184291-89-2
• 化学式: C₆₆H₁₂₃N₃O₁₂Si₃
• 分子量: 1234.97
• InChiKey: OVEFTZTZYNUSOB-BYXJBARPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.12
• 重原子数：
  84.0
• 可旋转键数：
  37.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  203.2
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3,7,11-tris[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9-[({[({5-[(2-propenyloxy)carbonyl]amino}hexyl)amino]carbonyl}oxy)pentyl]discodermolide 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以60%的产率得到prop-2-enyl N-[6-[[(6S,8Z,10S,11S,12S,13Z,15S)-6-[(1R,2S,3S,4S,5Z)-3-carbamoyloxy-1-hydroxy-2,4-dimethylocta-5,7-dienyl]-11,15-dihydroxy-16-[(2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxooxan-2-yl]-8,10,12-trimethylhexadeca-8,13-dienoxy]carbonylamino]hexyl]carbamate
  参考文献：
  名称：

  Syntheses of Discodermolides Useful for Investigating Microtubule Binding and Stabilization

  摘要：

  Discodermolide is a marine natural product reported to inhibit the proliferation of T cells and exhibit immunosuppresive activity. Total syntheses of the natural antipode of discodermolide and several variants are reported. These studies provide reagents to investigate discodermolide's recently discovered ability to bind and stabilize microtubules in cells, Retrosynthetically, the polypropionate is divided into three fragments of approximately equal complexity. This modular strategy provides convergency in the synthesis and facilitates the preparation of discodermolide-based reagents.

  DOI：

  10.1021/ja961374o
• 作为产物：
  描述：

  [2S-(2β(3Z,5S,6S,7R,9S,11Z,13S,14S,15S,16Z,18S),3β,4β,5α,6α)]-14,18-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-19-{4-[(1,1-dimethylethyl)dimethylsilyl]oxy}tetrahydro-3,5-dimethyl-6-(phenylthio)-2H-pyran-2-yl-6-[(4-methoxyphenyl)methoxy]-9- 在 aluminum oxide 、 jones reagent 、 pH 7 buffer 、 碳酸氢钠 、 lithium tri-t-butoxyaluminum hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 mercury dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 8.0h， 生成 3,7,11-tris[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9-[({[({5-[(2-propenyloxy)carbonyl]amino}hexyl)amino]carbonyl}oxy)pentyl]discodermolide
  参考文献：
  名称：

  Syntheses of Discodermolides Useful for Investigating Microtubule Binding and Stabilization

  摘要：

  Discodermolide is a marine natural product reported to inhibit the proliferation of T cells and exhibit immunosuppresive activity. Total syntheses of the natural antipode of discodermolide and several variants are reported. These studies provide reagents to investigate discodermolide's recently discovered ability to bind and stabilize microtubules in cells, Retrosynthetically, the polypropionate is divided into three fragments of approximately equal complexity. This modular strategy provides convergency in the synthesis and facilitates the preparation of discodermolide-based reagents.

  DOI：

  10.1021/ja961374o