imidazole-1-carboxylic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester | 870646-17-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: imidazole-1-carboxylic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester
• CAS: 870646-17-6
• 化学式: C₆₀H₁₁₂N₂O₈Si₄
• 分子量: 1101.9
• InChiKey: SKJUXPSRBWTJAZ-TUIMYHBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.2
• 重原子数：
  74.0
• 可旋转键数：
  24.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  107.34
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  imidazole-1-carboxylic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester 在 盐酸 、 碘甲烷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 生成 [(3Z,5S,6S,7S,8R,9S,11Z,13S,14S,15S,16Z,18S)-8,14,18-trihydroxy-19-[(2S,3R,4S,5R)-4-hydroxy-3,5-dimethyl-6-oxooxan-2-yl]-5,7,9,11,13,15-hexamethylnonadeca-1,3,11,16-tetraen-6-yl] N-(3-morpholin-4-ylpropyl)carbamate
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Carbamate-Substituted Analogues of (+)-Discodermolide

  摘要：

  The design, syntheses, and biological evaluation of 22 totally synthetic analogues of the potent microtubule-stabilizing agent (divided by)-discodermolide (1) have been achieved. Structure-activity relationships of the C(19) carbamate were defined. exploiting two synthetically simplified scaffolds. as well as the parent (+)-discodermolide framework.

  DOI：

  10.1021/ol047686a
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 (3R,4S,5S,6S)-4-[tert-butyl(dimethyl)silyl]oxy-3,5-dimethyl-6-[(2S,3Z,5S,6S,7S,8Z,11S,12R,13R,14S,15S,16Z)-2,6,12-tris[[tert-butyl(dimethyl)silyl]oxy]-14-hydroxy-5,7,9,11,13,15-hexamethylnonadeca-3,8,16,18-tetraenyl]oxan-2-one 以 二氯甲烷 为溶剂， 反应 12.0h， 以61%的产率得到imidazole-1-carboxylic acid 3,9,13-tris-(tert-butyl-dimethyl-silanyloxy)-14-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl]-2,4,6,8,10-pentamethyl-1-(1-methyl-penta-2,4-dienyl)-tetradeca-6,11-dienyl ester
  参考文献：
  名称：

  设计，合成和生物学评估有效的discodemolide荧光和光亲和力分子探针。

  摘要：

  [结构：见正文]已经完成了一系列具有光亲和性和荧光附件的（+）-discodermolide分子探针的设计，合成和生物学评估。立体选择性烯烃交叉复分解是构建两个分子探针的关键策略。用tri对三种光亲和探针进行放射性标记。

  DOI：

  10.1021/ol0520166