methyl (E,4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-iodohex-5-enoate | 1352963-71-3

• 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 (E,4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-iodohex-5-enoate
• CAS: 1352963-71-3
• 化学式: C₁₃H₂₅IO₃Si
• 分子量: 384.33
• InChiKey: YINNJCBKAYYQKK-USKTWTLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  methyl (E,4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-iodohex-5-enoate 在 盐酸 、 甲醇 、 正丙胺 、 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 苯 为溶剂， 生成 C₂₃H₃₀O₄
  参考文献：
  名称：

  First total synthesis of the anti-inflammatory lipid mediator Resolvin D6

  摘要：

  The first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7-C14 fragment. Pd-0/Cu-I Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.003
• 作为产物：
  描述：

  (S)-Methyl 4-hydroxyhex-5-ynoate 在 咪唑 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (E,4S)-4-[tert-butyl(dimethyl)silyl]oxy-6-iodohex-5-enoate
  参考文献：
  名称：

  First total synthesis of the anti-inflammatory lipid mediator Resolvin D6

  摘要：

  The first total synthesis of Resolvin D6, an endogenous lipid mediator of resolution of inflammation derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-groups at C4 and C17 were generated via an asymmetric Noyori transfer hydrogenation and a Sharpless catalytic asymmetric epoxidation, respectively. A mild copper catalyzed coupling of cis-1,4-dibromo-2-butene with TMS-acetylene generated the C7-C14 fragment. Pd-0/Cu-I Sonogashira couplings and Zn(Cu/Ag) reduction completed the synthesis of Resolvin D6. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.003