(Z)-(R)-8-Hydroxy-8-[(2S,4S,5S)-4-hydroxy-5-((E)-(S)-3-hydroxy-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enoic acid | 793673-18-4

• 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: (Z)-(R)-8-Hydroxy-8-[(2S,4S,5S)-4-hydroxy-5-((E)-(S)-3-hydroxy-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enoic acid
• 英文别名: (8R,11S,15S)-d13-9-IsoF[9S,12S]；(Z,8R)-8-hydroxy-8-[(2S,4S,5S)-4-hydroxy-5-[(E,3S)-3-hydroxyoct-1-enyl]oxolan-2-yl]oct-5-enoic acid
• CAS: 793673-18-4
• 化学式: C₂₀H₃₄O₆
• 分子量: 370.486
• InChiKey: WNNXWLICSWATQV-GKWCVUCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三甲基硅烷化重氮甲烷 、 (Z)-(R)-8-Hydroxy-8-[(2S,4S,5S)-4-hydroxy-5-((E)-(S)-3-hydroxy-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enoic acid 以 甲醇 、 苯 为溶剂， 反应 1.0h， 以100%的产率得到(Z)-(R)-8-Hydroxy-8-[(2S,4S,5S)-4-hydroxy-5-((E)-(S)-3-hydroxy-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enoic acid methyl ester
  参考文献：
  名称：

  A Flexible Enantioselective Synthesis of the Isofurans

  摘要：

  Recently, the isolation of a new class of human arachidonic acid tetrahydrofuran oxidation products, the isofurans (IsoF's), was reported. These new compounds are available from natural sources only in microgram quantities as mixtures. The enantioselective preparation of a versatile epoxide intermediate and its conversion to the enantiomerically pure isofurans SC-Delta(13)-9-IsoF and 15-epi-SC-Delta(13)-9-IsoF are described. This synthesis will make these metabolites available for physiological evaluation.

  DOI：

  10.1021/jo048863o
• 作为产物：
  描述：

  1,(trimethylsilyloxy)hexa-1,3,5-triene 在 Mi(OAc)2*4H₂O 咪唑 、 titanium(IV) isopropylate 、 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 AD-mix-α 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 正丁基锂 、 L-(+)-酒石酸二乙酯 、 甲基磺酰胺 、 四丁基氟化铵 、 氢气 、 溴 、 potassium carbonate 、 乙二胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 正庚烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 叔丁醇 为溶剂， 反应 123.33h， 生成 (Z)-(R)-8-Hydroxy-8-[(2S,4S,5S)-4-hydroxy-5-((E)-(S)-3-hydroxy-oct-1-enyl)-tetrahydro-furan-2-yl]-oct-5-enoic acid
  参考文献：
  名称：

  A Flexible Enantioselective Synthesis of the Isofurans

  摘要：

  Recently, the isolation of a new class of human arachidonic acid tetrahydrofuran oxidation products, the isofurans (IsoF's), was reported. These new compounds are available from natural sources only in microgram quantities as mixtures. The enantioselective preparation of a versatile epoxide intermediate and its conversion to the enantiomerically pure isofurans SC-Delta(13)-9-IsoF and 15-epi-SC-Delta(13)-9-IsoF are described. This synthesis will make these metabolites available for physiological evaluation.

  DOI：

  10.1021/jo048863o

文献信息

• A Divergent Synthesis of the Δ¹³-9-Isofurans
  作者：Douglass F. Taber、Peiming Gu、Rui Li

  DOI：10.1021/jo900767x

  日期：2009.8.7

  stereodivergent total synthesis of the Δ13-9-isofurans has been developed. The four core substituted tetrahydrofurans were prepared by the Sharpless asymmetric epoxidation and Sharpless asymmetric dihydroxylation followed by cascade cyclization. The relative configuration at C-8 was inverted by oxidation followed by immediate L-Selectride reduction. The relative configuration of the C-15 diastereomers was

  已经开发了 Δ 13 -9-异呋喃的立体发散全合成。四个核心取代的四氢呋喃是通过 Sharpless 不对称环氧化和 Sharpless 不对称二羟基化随后级联环化制备的。C-8 处的相对构型通过氧化被反转，然后立即 L-Selectride 还原。C-15 非对映体的相对构型由相应烯酮的 ( S )-Binol/LAH/EtOH 还原指定。Δ 13 -9-异呋喃的这种合成将为进一步研究它们的生物活性提供足够的材料。
• A Flexible Enantioselective Synthesis of the Isofurans
  作者：Douglass F. Taber、Yongchun Pan、Xia Zhao

  DOI：10.1021/jo048863o

  日期：2004.10.1

  Recently, the isolation of a new class of human arachidonic acid tetrahydrofuran oxidation products, the isofurans (IsoF's), was reported. These new compounds are available from natural sources only in microgram quantities as mixtures. The enantioselective preparation of a versatile epoxide intermediate and its conversion to the enantiomerically pure isofurans SC-Delta(13)-9-IsoF and 15-epi-SC-Delta(13)-9-IsoF are described. This synthesis will make these metabolites available for physiological evaluation.