(5S)-3-[(2R,8R)-2-(tert-butyldimethylsilyloxy)-8,9-epoxynonan-1-yl]-5-methyl-3,4-dihydrofuran-2-one | 1011733-71-3

• 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: (5S)-3-[(2R,8R)-2-(tert-butyldimethylsilyloxy)-8,9-epoxynonan-1-yl]-5-methyl-3,4-dihydrofuran-2-one
• 英文别名: (2S)-4-[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-7-[(2R)-oxiran-2-yl]heptyl]-2-methyl-2H-furan-5-one
• CAS: 1011733-71-3
• 化学式: C₂₀H₃₆O₄Si
• 分子量: 368.589
• InChiKey: OEWDOGPFDMWWAL-CGTJXYLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5S)-3-[(2R,8R)-2-(tert-butyldimethylsilyloxy)-8,9-epoxynonan-1-yl]-5-methyl-3,4-dihydrofuran-2-one 在 正丁基锂 、 二甲基硫 、 三氟化硼乙醚 、 sodium acetate 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 正己烷 、 乙二醇二乙醚 为溶剂， 反应 8.0h， 生成 番荔枝素
  参考文献：
  名称：

  Synthesis of Annonacin Isolated fromAnnona densicoma

  摘要：

  通过使用多功能手性结构单元2合成单四氢呋喃（THF）番荔枝属植物乙酰基苷，完成了番荔枝属植物苷（1）的全合成。

  DOI：

  10.1271/bbb.90902
• 作为产物：
  描述：

  (5S)-3-[(2R)-2-(tert-butyldimethylsilyloxy)-8,9-epoxynonan-1-yl]-5-methyl-3,4-dihydrofuran-2-one 在 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以43%的产率得到(5S)-3-[(2R,8R)-2-(tert-butyldimethylsilyloxy)-8,9-epoxynonan-1-yl]-5-methyl-3,4-dihydrofuran-2-one
  参考文献：
  名称：

  Synthesis of pyranicin and its deoxygenated analogues and their inhibitory action with bovine heart mitochondrial complex I

  摘要：

  Total synthesis of pyranicin and its deoxygenated analogues was achieved using Cl(2)Pd(CH(3)CN)(2) catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of these compounds for mitochondrial NADH-ubiquinone oxicloreductase (complex I) was poorer than those of ordinary mono-THF acetogenins such as annonacin. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.06.028

文献信息

• Synthesis of Pyranicin and Its Inhibitory Action with Bovine Heart Mitochondrial Complex I
  作者：Yasunao Hattori、Shin-ichi Furuhata、Motonori Okajima、Hiroyuki Konno、Masato Abe、Hideto Miyoshi、Tetsuhisa Goto、Hidefumi Makabe

  DOI：10.1021/ol702902w

  日期：2008.3.1

  Total synthesis of pyranicin was achieved using Cl2Pd(CH3CN)(2)-catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of this compound for mitochondrial NADH-ubiquinone oxidoreductase (complex I) was slightly poorer than that of ordinary mono-THF acetogenins such as cis-solamin.
• Synthesis of pyranicin and its deoxygenated analogues and their inhibitory action with bovine heart mitochondrial complex I
  作者：Shin-ichi Furuhata、Yasunao Hattori、Motonori Okajima、Hiroyuki Konno、Masato Abe、Hideto Miyoshi、Tetsuhisa Goto、Hidefumi Makabe

  DOI：10.1016/j.tet.2008.06.028

  日期：2008.8

  Total synthesis of pyranicin and its deoxygenated analogues was achieved using Cl(2)Pd(CH(3)CN)(2) catalyzed diastereoselective cyclization of the allylic ester as the key step. The inhibitory activity of these compounds for mitochondrial NADH-ubiquinone oxicloreductase (complex I) was poorer than those of ordinary mono-THF acetogenins such as annonacin. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Annonacin Isolated from<i>Annona densicoma</i>
  作者：Mayu OASA、Yasunao HATTORI、Hiroyuki KONNO、Hidefumi MAKABE

  DOI：10.1271/bbb.90902

  日期：2010.6.23

  A total synthesis of annonacin (1) was accomplished by using versatile chiral building block 2 for synthesizing the mono-tetrahydrofuran (THF) annonaceous acetogenins.

  通过使用多功能手性结构单元2合成单四氢呋喃（THF）番荔枝属植物乙酰基苷，完成了番荔枝属植物苷（1）的全合成。