2,2-Dimethyl-propionic acid (Z)-(4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-oct-2-en-7-ynyl ester | 184488-82-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,2-Dimethyl-propionic acid (Z)-(4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-oct-2-en-7-ynyl ester
• CAS: 184488-82-2
• 化学式: C₂₂H₄₀O₃Si
• 分子量: 380.643
• InChiKey: XWLRIZLROFUMEY-IIYQRABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (Z)-(4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-oct-2-en-7-ynyl ester 在 palladium on activated charcoal 吗啉 、 2,6-二甲基吡啶 、 chromium dichloride 、 盐酸 、 aluminum oxide 、 lithium bis(dimethylphenylsilyl)amide 、 Jones oxidant 、 pH 7 buffer 、 氢气 、 碘 、 二异丁基氢化铝 、 碳酸氢钠 、 lithium tri-t-butoxyaluminum hydride 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 mercury dichloride 、 lithium bromide 、 nickel dichloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 丙酮 、 乙腈 、 苯 为溶剂， 反应 110.67h， 生成 [(5E,7Z,9S,10S,11S,12R,13S,15Z,17S,18S,19S,20Z,22S)-10-carbamoyloxy-12,18,22-trihydroxy-23-[(2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxooxan-2-yl]-9,11,13,15,17,19-hexamethyltricosa-5,7,15,20-tetraenyl] 2,2-dimethylpropanoate
  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,3R,4S)-1-(tert-butyldimethylsilyloxy)-2,4-dimethylhex-5-en-3-ol 在 吡啶 、 lithium aluminium tetrahydride 、 草酰氯 、 18-冠醚-6 、 二甲基硫 、 氢氟酸 、 potassium tert-butylate 、 双(三甲基硅烷基)氨基钾 、 臭氧 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 53.42h， 生成 2,2-Dimethyl-propionic acid (Z)-(4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-oct-2-en-7-ynyl ester
  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