2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate | 439808-15-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate
• 英文别名: AK-toxin I 2-(trimethylsilyl)ethyl ester；2-trimethylsilylethyl (2E,4Z,6E,8R)-8-[(2S,3S)-2-acetamido-3-phenylbutanoyl]oxy-8-[(2S)-2-methyloxiran-2-yl]octa-2,4,6-trienoate
• CAS: 439808-15-8
• 化学式: C₂₈H₃₉NO₆Si
• 分子量: 513.706
• InChiKey: LKJQINBUVJCJIT-CFPCKLPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以73%的产率得到(2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoic acid
  参考文献：
  名称：

  Asymmetric total synthesis of AK-toxins

  摘要：

  A practical total synthesis of AK-toxins (AK-toxin I, 1; II, 2), host-specific toxins against the Japanese pear, has been achieved in 10% total yield, starting from the key intermediate 6. The (2E,4Z,6E)-conjugated triene system was successfully constructed by the use of the Stille coupling reaction between the (E,Z)-bromodiene (17) and (E)-stannylacrylate (21). The (E,Z)-configuration of 17 was established with excellent geometrical purity by palladium-catalyzed stereoselective hydrogenolysis of gem-dibromide (15), which was derived from 6 via the Wittig-Horner reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00117-5
• 作为产物：
  描述：

  (2R,3S)-2-(tert-butyldiphenylsilyl)oxy-3,4-epoxy-3-methylbutanal 在 bis-triphenylphosphine-palladium(II) chloride 、 palladium diacetate 哌啶 、 吡啶 、 四丁基氟化铵 、 三正丁基氢锡 、 4-吡咯烷基吡啶 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 、 苯 为溶剂， 反应 15.5h， 生成 2-(trimethylsilyl)ethyl (2E,4Z,6E,8R,9S,2'S,3'S)-8-(2'-acetylamino-3'-phenylbutanoyloxy)-9,10-epoxy-9-methyldeca-2,4,6-trienoate
  参考文献：
  名称：

  Asymmetric total synthesis of AK-toxins

  摘要：

  A practical total synthesis of AK-toxins (AK-toxin I, 1; II, 2), host-specific toxins against the Japanese pear, has been achieved in 10% total yield, starting from the key intermediate 6. The (2E,4Z,6E)-conjugated triene system was successfully constructed by the use of the Stille coupling reaction between the (E,Z)-bromodiene (17) and (E)-stannylacrylate (21). The (E,Z)-configuration of 17 was established with excellent geometrical purity by palladium-catalyzed stereoselective hydrogenolysis of gem-dibromide (15), which was derived from 6 via the Wittig-Horner reactions. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00117-5