(2Z,7Z,15Z)-(4S,5S,6S,10R,11R,12R,13S,14S)-5,11-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-13-hydroxy-4,6,8,12,14-pentamethyl-octadeca-2,7,15,17-tetraenoic acid methyl ester | 646031-62-1

• 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: (2Z,7Z,15Z)-(4S,5S,6S,10R,11R,12R,13S,14S)-5,11-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-13-hydroxy-4,6,8,12,14-pentamethyl-octadeca-2,7,15,17-tetraenoic acid methyl ester
• CAS: 646031-62-1
• 化学式: C₄₃H₈₄O₆Si₃
• 分子量: 781.393
• InChiKey: CPVWAIDHZVYCBR-LQTUJNJKSA-N

物化性质

• 沸点：
  680.5±55.0 °C(Predicted)
• 密度：
  0.925±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.12
• 重原子数：
  52.0
• 可旋转键数：
  20.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2Z,7Z,15Z)-(4S,5S,6S,10R,11R,12R,13S,14S)-5,11-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-13-hydroxy-4,6,8,12,14-pentamethyl-octadeca-2,7,15,17-tetraenoic acid methyl ester 在 (+)-β-chlorodiisopinocampheylborane 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 溶剂黄146 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 25.5h， 生成
  参考文献：
  名称：

  Synthesis of novel discodermolide analogues with modified hydrogen-bonding donor/acceptor sites

  摘要：

  A series of novel structural analogues of the potent microtubule-stabilizing anticancer agent discodermolide were synthesised, with modifications in the C16-C20 region to create new oxygenated H-bonding donor/acceptor sites for tubulin binding. By starting from an advanced C9-C24 intermediate, fully synthetic discodermolide analogues, incorporating either an additional hydroxyl group 3, an oxetane 4 or a cyclic carbonate 5, were obtained in 10 or 11 steps by using a versatile aldol construction of the C6-C7 bond. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.172
• 作为产物：
  描述：

  (3Z,5S,6S,7S,8R,9R,11Z,13S,14R,15S)-14-(t-butyldimethylsilyloxy)-6,16-bis(p-methoxybenzyloxy)-9-(hydroxymethyl)-5,7,11,13,15-pentamethylhexadeca-1,3,11-trien-8-ol 在 2,6-二甲基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 18-冠醚-6 、 碘苯二乙酸 、 potassium carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 生成 (2Z,7Z,15Z)-(4S,5S,6S,10R,11R,12R,13S,14S)-5,11-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(tert-butyl-dimethyl-silanyloxymethyl)-13-hydroxy-4,6,8,12,14-pentamethyl-octadeca-2,7,15,17-tetraenoic acid methyl ester
  参考文献：
  名称：

  Synthesis of novel discodermolide analogues with modified hydrogen-bonding donor/acceptor sites

  摘要：

  A series of novel structural analogues of the potent microtubule-stabilizing anticancer agent discodermolide were synthesised, with modifications in the C16-C20 region to create new oxygenated H-bonding donor/acceptor sites for tubulin binding. By starting from an advanced C9-C24 intermediate, fully synthetic discodermolide analogues, incorporating either an additional hydroxyl group 3, an oxetane 4 or a cyclic carbonate 5, were obtained in 10 or 11 steps by using a versatile aldol construction of the C6-C7 bond. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.172