Carbamic acid (6Z,11Z)-(1S,2R,3R,4R,8S,9S,10S)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-13-oxo-trideca-6,11-dienyl ester | 646031-63-2

• 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: Carbamic acid (6Z,11Z)-(1S,2R,3R,4R,8S,9S,10S)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-13-oxo-trideca-6,11-dienyl ester
• 英文别名: [(3Z,5S,6S,7R,8R,9R,11Z,13S,14S,15S,16Z)-8,14-bis[[tert-butyl(dimethyl)silyl]oxy]-9-[[tert-butyl(dimethyl)silyl]oxymethyl]-5,7,11,13,15-pentamethyl-18-oxooctadeca-1,3,11,16-tetraen-6-yl] carbamate
• CAS: 646031-63-2
• 化学式: C₄₃H₈₃NO₆Si₃
• 分子量: 794.392
• InChiKey: TVNHWHDKGJDMNS-SLPZKADWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.25
• 重原子数：
  53
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  97.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Carbamic acid (6Z,11Z)-(1S,2R,3R,4R,8S,9S,10S)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-13-oxo-trideca-6,11-dienyl ester 在 (+)-β-chlorodiisopinocampheylborane 、 溶剂黄146 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 18.5h， 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：

  (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 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 Carbamic acid (6Z,11Z)-(1S,2R,3R,4R,8S,9S,10S)-3,9-bis-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-2,6,8,10-tetramethyl-1-((Z)-(S)-1-methyl-penta-2,4-dienyl)-13-oxo-trideca-6,11-dienyl 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

文献信息

• Synthesis of novel discodermolide analogues with modified hydrogen-bonding donor/acceptor sites
  作者：Ian Paterson、Oscar Delgado

  DOI：10.1016/j.tetlet.2003.09.172

  日期：2003.12

  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.