(S)-(5Z,8Z)-11-[tert-butoxycarbonyl-(2-{(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienyloxy}ethyl)amino]tetradeca-5,8-dienoic acid | 329184-81-8

• 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: (S)-(5Z,8Z)-11-[tert-butoxycarbonyl-(2-{(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienyloxy}ethyl)amino]tetradeca-5,8-dienoic acid
• 英文别名: (5Z,8Z,11S)-11-[2-[(5Z,8Z,11S)-11-[2-[tert-butyl(diphenyl)silyl]oxyethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]tetradeca-5,8-dienoyl]oxyethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]tetradeca-5,8-dienoic acid
• CAS: 329184-81-8
• 化学式: C₅₈H₉₀N₂O₉Si
• 分子量: 987.446
• InChiKey: DSCAPSXXQUEIIM-ZAODRKPMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.13
• 重原子数：
  70
• 可旋转键数：
  37
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (S)-(5Z,8Z)-11-[tert-butoxycarbonyl-(2-{(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienyloxy}ethyl)amino]tetradeca-5,8-dienoic acid 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以94%的产率得到(S)-(5Z,8Z)-11-[tert-butoxycarbonyl-(2-{(S)-(5Z,8Z)-11-[(tert-butoxycarbonyl)-(2-hydroxyethyl)amino]tetradeca-5,8-dienyloxy}ethyl)amino]tetradeca-5,8-dienoic acid
  参考文献：
  名称：

  Synthesis of Unsaturated Polyazamacrolides from the Ladybird Beetle Subcoccinella vigintiquatuorpunctata

  摘要：

  The pupal defensive secretion of the ladybird beetle Subcoccinella vigintiquatuorpunctata consists of a mixture of macrocyclic polyamines (polyazamacrolides, PAMLs) dominated by three dimeric, 30-membered bislactones (1, 2, and 3), which represent the three possible head-to-tail combinations of the two building blocks (S)-(Z)-11-(2-hydroxyethylamino)-5-tetradecenoic acid (4) and (S)-(5Z,8Z)-11-(2-hydroxyethylamino)-5,8-tetradecadienoic acid (5). We now report the synthesis of these three alkaloids via a route involving the nucleophilic opening of a chiral aziridine as a common step.

  DOI：

  10.1021/jo001200w
• 作为产物：
  描述：

  4-methyl-N-[(S)-1-propyl-5-(tetrahydropyran-2-yloxy)pent-3-ynyl]benzenesulfonamide 在 palladium diacetate 、 Lindlar's catalyst 吗啉 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium hydrogen sulfate 、 copper(l) iodide 、 正丁基锂 、 萘 、 四丁基氟化铵 、 氢气 、 溴 、 sodium 、 sodium hydride 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 136.5h， 生成 (S)-(5Z,8Z)-11-[tert-butoxycarbonyl-(2-{(S)-(5Z,8Z)-11-[[2-(tert-butyldiphenylsilanyloxy)ethyl](dimethylethoxycarbonyl)amino]tetradeca-5,8-dienyloxy}ethyl)amino]tetradeca-5,8-dienoic acid
  参考文献：
  名称：

  Synthesis of Unsaturated Polyazamacrolides from the Ladybird Beetle Subcoccinella vigintiquatuorpunctata

  摘要：

  The pupal defensive secretion of the ladybird beetle Subcoccinella vigintiquatuorpunctata consists of a mixture of macrocyclic polyamines (polyazamacrolides, PAMLs) dominated by three dimeric, 30-membered bislactones (1, 2, and 3), which represent the three possible head-to-tail combinations of the two building blocks (S)-(Z)-11-(2-hydroxyethylamino)-5-tetradecenoic acid (4) and (S)-(5Z,8Z)-11-(2-hydroxyethylamino)-5,8-tetradecadienoic acid (5). We now report the synthesis of these three alkaloids via a route involving the nucleophilic opening of a chiral aziridine as a common step.

  DOI：

  10.1021/jo001200w