(2R,3R,6R)-2-dodecyl-3-(methoxymethoxy)-6-[(1R)-1-(methoxymethoxy)-3-butyn-1-yl]tetrahydropyran | 1011733-70-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,6R)-2-dodecyl-3-(methoxymethoxy)-6-[(1R)-1-(methoxymethoxy)-3-butyn-1-yl]tetrahydropyran
• 英文别名: (2R,3R,6R)-2-dodecyl-3-(methoxymethoxy)-6-[(1R)-1-(methoxymethoxy)but-3-ynyl]oxane
• CAS: 1011733-70-2
• 化学式: C₂₅H₄₆O₅
• 分子量: 426.637
• InChiKey: CHHYOIMBUOFODC-ZGFBMJKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  30
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

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 、 (2R,3R,6R)-2-dodecyl-3-(methoxymethoxy)-6-[(1R)-1-(methoxymethoxy)-3-butyn-1-yl]tetrahydropyran 在 正丁基锂 、 三氟化硼乙醚 作用下， 以 正己烷 为溶剂， 反应 3.5h， 以75%的产率得到(2R,3R,6R)-6-{(1R,6R,12R)-12-(tert-butyldimethylsilyloxy)-6-hydroxy-1-(methoxymethoxy)-13-[(5S)-5-methyl-3,4-dihydrofuran-2-on-3-yl]tridec-3-ynyl}-2-dodecyl-3-(methoxymethoxy)tetrahydropyran
  参考文献：
  名称：

  Synthesis of Pyranicin and Its Inhibitory Action with Bovine Heart Mitochondrial Complex I

  摘要：

  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.

  DOI：

  10.1021/ol702902w
• 作为产物：
  描述：

  溴甲基甲基醚 、 (2R,3R,6R)-2-dodecyl-6-[(1R)-1-hydroxy-3-butyn-1-yl]tetrahydropyran-3-ol 在 N,N-二异丙基乙胺 作用下， 反应 16.0h， 以77%的产率得到(2R,3R,6R)-2-dodecyl-3-(methoxymethoxy)-6-[(1R)-1-(methoxymethoxy)-3-butyn-1-yl]tetrahydropyran
  参考文献：
  名称：

  Synthesis of Pyranicin and Its Inhibitory Action with Bovine Heart Mitochondrial Complex I

  摘要：

  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.

  DOI：

  10.1021/ol702902w

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.