methyl (S,E)-5-((4R,5R)-5-((2S,3R)-2-hydroxy-3-methylpent-4-en-1-yl)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-4-methylpent-2-enoate | 1549648-78-3

• 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: methyl (S,E)-5-((4R,5R)-5-((2S,3R)-2-hydroxy-3-methylpent-4-en-1-yl)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-4-methylpent-2-enoate
• CAS: 1549648-78-3
• 化学式: C₁₉H₃₂O₅
• 分子量: 340.46
• InChiKey: WWENVXNNLXTCHW-CKZLGTCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (S,E)-5-((4R,5R)-5-((2S,3R)-2-hydroxy-3-methylpent-4-en-1-yl)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-4-methylpent-2-enoate 在 2,6-二甲基吡啶 、 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.5h， 生成
  参考文献：
  名称：

  Synthesis of amphidinolide Y precursors

  摘要：

  The Negishi coupling between a chiral C3 synthon and an iodoalkene arising from 3-butyn-l-ol, which gave the C3-C9 fragment of amphidinolide Y, was the starting point of a formal total synthesis of this marine natural product. By means of Sharpless ADH and TADDOL-mediated crotylation, the full western fragment (C1-C11) was obtained, which was coupled with the eastern fragment (3-hydroxyoxolane derivative). The penultimate step (ring-closing metathesis, with G-II, H-G-II, or Nitro-Grela reagents, under several conditions) posed great difficulties. The cyclization was achieved with 15c (7,9-bis-O-TES) and 15d (7-O-TES, 9-O-TBS); more than stoichiometric amounts of the H-G-II Ru complex were required for complete conversion. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.047
• 作为产物：
  描述：

  在 (4S,5S)-chloro(cyclopentadienyl)(2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato-O,O^α)titanium 、 四丁基氟化铵 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 57.0h， 生成 methyl (S,E)-5-((4R,5R)-5-((2S,3R)-2-hydroxy-3-methylpent-4-en-1-yl)-2,2,5-trimethyl-1,3-dioxolan-4-yl)-4-methylpent-2-enoate
  参考文献：
  名称：

  Synthesis of amphidinolide Y precursors

  摘要：

  The Negishi coupling between a chiral C3 synthon and an iodoalkene arising from 3-butyn-l-ol, which gave the C3-C9 fragment of amphidinolide Y, was the starting point of a formal total synthesis of this marine natural product. By means of Sharpless ADH and TADDOL-mediated crotylation, the full western fragment (C1-C11) was obtained, which was coupled with the eastern fragment (3-hydroxyoxolane derivative). The penultimate step (ring-closing metathesis, with G-II, H-G-II, or Nitro-Grela reagents, under several conditions) posed great difficulties. The cyclization was achieved with 15c (7,9-bis-O-TES) and 15d (7-O-TES, 9-O-TBS); more than stoichiometric amounts of the H-G-II Ru complex were required for complete conversion. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.047