ethyl (2E,5S)-7-{[tert-butyl(dimethyl)silyloxy]methyl}-5-methylocta-2,7-dienoate | 202581-39-3

• 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: ethyl (2E,5S)-7-{[tert-butyl(dimethyl)silyloxy]methyl}-5-methylocta-2,7-dienoate
• 英文别名: Ethyl (2e,5s)-7-{[t-butyl(dimethyl)silyloxy]-methyl}-5-methylocta-2,7-dienoate；ethyl (2E,5S)-7-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-methylocta-2,7-dienoate
• CAS: 202581-39-3
• 化学式: C₁₈H₃₄O₃Si
• 分子量: 326.552
• InChiKey: GNJYVWBUMTVRHQ-PABFRNLHSA-N

物化性质

• 沸点：
  363.8±42.0 °C(Predicted)
• 密度：
  0.906±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2E,5S)-7-{[tert-butyl(dimethyl)silyloxy]methyl}-5-methylocta-2,7-dienoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以94%的产率得到ethyl (2E,5S)-7-(hydroxymethyl)-5-methylocta-2,7-dienoate
  参考文献：
  名称：

  (3S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutan-1-ol—A universal building block for the synthesis of principal fragments of amphidinolides G and H

  摘要：

  A new scheme has been proposed for the synthesis of cytotoxic macrocyclic lactones, amphidinolides G and H. Synthetic analogs of the C(7)aEuro'C-14, C(15)aEuro'C-19, and C(20)aEuro'C-26 fragments of amphidinolides G and H have been prepared from the same starting compound, (3S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutan-1-ol. The developed procedures and obtained products may be used in the synthesis of related compounds containing similar structural fragments.

  DOI：

  10.1134/s1070428016010206
• 作为产物：
  描述：

  ethyl (2E,5S,7R)-8-{[tert-butyl(dimethyl)silyl]oxy}-7-hydroxy-5-methyloct-2-enoate 在 草酰氯 、 potassium tert-butylate 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 ethyl (2E,5S)-7-{[tert-butyl(dimethyl)silyloxy]methyl}-5-methylocta-2,7-dienoate
  参考文献：
  名称：

  (3S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutan-1-ol—A universal building block for the synthesis of principal fragments of amphidinolides G and H

  摘要：

  A new scheme has been proposed for the synthesis of cytotoxic macrocyclic lactones, amphidinolides G and H. Synthetic analogs of the C(7)aEuro'C-14, C(15)aEuro'C-19, and C(20)aEuro'C-26 fragments of amphidinolides G and H have been prepared from the same starting compound, (3S)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-methylbutan-1-ol. The developed procedures and obtained products may be used in the synthesis of related compounds containing similar structural fragments.

  DOI：

  10.1134/s1070428016010206

文献信息

• New 2-substituted functionalized allyl halides in the synthesis of fragments of amphidinolides B, D, G, H, and L
  作者：I. V. Mineeva

  DOI：10.1134/s1070428017030204

  日期：2017.3

  asymmetric syntheses of several new allyl bromides as C9–C14 fragments of cytotoxic macrolactones, amphidinolides B, D, G, H, and L, have been developed starting from accessible 1-[(2S)-4,4-dimethoxy-2-methylbutyl]cyclopropyl methanesulfonate prepared through cyclopropanol intermediates. Original synthetic approaches to the C7–C16, C7–C14, and C9–C16 amphidinolide fragments are also described.

  从有效的1-[（2 S）-4,4开始，开发了几种新的烯丙基溴的简单有效的不对称合成物，作为细胞毒性大内酯，两性霉素B，D，G，H和L的C 9 –C 14片段。通过环丙醇中间体制得-二甲氧基-2-甲基丁基]环丙基甲磺酸酯。还描述了对C 7 -C 16，C 7 -C 14和C 9 -C 16苯二环内酯片段的原始合成方法。
• Synthesis of two diastereomers of C-1 ∼ C-14 segment in amphidinolide L
  作者：Jun'ichi Kobayashi、Akiko Hatakeyama、Masashi Tsuda

  DOI：10.1016/s0040-4020(97)10293-9

  日期：1998.1

  In order to determine the stereochemistry of amphidinolide L (1), a cytotoxic macrolide from a marine dinoflagellate, (8S,9S,11R)-2a and (8R,9R,11R)-2b, two diastereomers of the C-1 similar to C-14 segment and (8S,9S,11R)-4a and (8R,9R,11R)-4b, two diastereomers of the C-7 similar to C-14 segment have been synthesized, providing authentic samples for degradation products of 1. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Synthesis of ethyl (2E,5S)-7-{[tert-butyl(dimethyl)silyloxy]-methyl}-5-methylocta-2,7-dienoate, a universal C7–C14 building block for the preparation of amphidinolides B, D, G, H, and L
  作者：I. V. Mineeva

  DOI：10.1134/s1070428015070052

  日期：2015.7

  A new simple and efficient procedure has been developed for the asymmetric synthesis of the C-7-C-14 building block for cytotoxic macrolactones, amphidinolides B, D, G, H, and L, on the basis of (4S,6S)-6-benzyloxymethyl-4-methyltetrahydro-2H-pyran-2-one prepared through cyclopropanol intermediates.