(2R,3R)-2,3-bis((tert-butyldimethylsilyl)oxy)pentan-1-ol | 1361013-76-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3R)-2,3-bis((tert-butyldimethylsilyl)oxy)pentan-1-ol
• CAS: 1361013-76-4
• 化学式: C₁₇H₄₀O₃Si₂
• 分子量: 348.674
• InChiKey: KZZDEKQVYOBHIC-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2,3-bis((tert-butyldimethylsilyl)oxy)pentan-1-ol 在 copper(l) iodide 、 正丁基锂 、 碳酸氢钠 、 potassium carbonate 、 caesium carbonate 、 戴斯-马丁氧化剂 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.55h， 生成 (5R,6R)-5-((1E,3E)-15-(1,3-dioxolan-2-yl)pentadeca-1,3-dien-5,8,11-triyn-1-yl)-6-ethyl-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane
  参考文献：
  名称：

  Total syntheses of four possible stereoisomers of resolvin E3

  摘要：

  Resolvin E3, 17,18-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid, is a potent anti-inflammatory lipid mediator. To determine the stereochemistries of the C17- and C18-hydroxy groups of resolvin E3 and to supply a sufficient amount of material for future biological studies, we developed a highly convergent and practical route to its four possible stereoisomers. The key reactions employed here were the Horner-Wadsworth-Emmons coupling, the two copper(I)-mediated reactions between the alkynes and the propargyl tosylates, and the simultaneous reduction of the three triple bonds to the three Z-olefins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.045
• 作为产物：
  描述：

  methyl (2S,3R)-2,3-bis((tert-butyldimethylsilyl)oxy)pentanoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.17h， 生成 (2R,3R)-2,3-bis((tert-butyldimethylsilyl)oxy)pentan-1-ol
  参考文献：
  名称：

  Total syntheses of four possible stereoisomers of resolvin E3

  摘要：

  Resolvin E3, 17,18-dihydroxy-5Z,8Z,11Z,13E,15E-eicosapentaenoic acid, is a potent anti-inflammatory lipid mediator. To determine the stereochemistries of the C17- and C18-hydroxy groups of resolvin E3 and to supply a sufficient amount of material for future biological studies, we developed a highly convergent and practical route to its four possible stereoisomers. The key reactions employed here were the Horner-Wadsworth-Emmons coupling, the two copper(I)-mediated reactions between the alkynes and the propargyl tosylates, and the simultaneous reduction of the three triple bonds to the three Z-olefins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.02.045

文献信息

• Design and Synthesis of Cyclopropane Congeners of Resolvin E3, an Endogenous Pro-Resolving Lipid Mediator, as Its Stable Equivalents
  作者：Shota Arai、Koichi Fujiwara、Masahiro Kojima、Haruka Aoki-Saito、Masakiyo Yatomi、Tsugumichi Saito、Yasuhiko Koga、Hayato Fukuda、Mizuki Watanabe、Shigeki Matsunaga、Takeshi Hisada、Satoshi Shuto

  DOI：10.1021/acs.joc.2c01110

  日期：2022.8.5

  Resolvins are pro-resolving lipid mediators with highly potent anti-inflammatory effects. Because of their polyunsaturated structures, however, they are unstable to oxygen as a drug prototype. To address this issue, we designed and synthesized CP-RvE3 as oxidatively stable congeners of RvE3 by replacing the cis-olefin with a cis-cyclopropane to avoid the unstable bisallylic structure. Although the

  Resolvins 是具有高效抗炎作用的促分解脂质介质。然而，由于它们的多不饱和结构，它们对氧作为药物原型不稳定。为了解决这个问题，我们设计并合成了 CP-RvE3 作为 RvE3 的氧化稳定同系物，通过用顺式环丙烷代替顺式烯烃来避免不稳定的双烯丙基结构。尽管 CP-RvE3 的氧化稳定性没有提高，但 β-CP-RvE3 的代谢稳定性是 RvE3 的 3.7 倍。因此，我们将 β-CP-RvE3 鉴定为代谢稳定的等效物。