(2R,3R,6R)-3-(tert-butyldimethylsilyloxy)-6-[(1S)-1,2-dihydroxyethyl]-2-dodecyltetrahydropyran | 1011733-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,6R)-3-(tert-butyldimethylsilyloxy)-6-[(1S)-1,2-dihydroxyethyl]-2-dodecyltetrahydropyran
• 英文别名: (1S)-1-[(2R,5R,6R)-5-[tert-butyl(dimethyl)silyl]oxy-6-dodecyloxan-2-yl]ethane-1,2-diol
• CAS: 1011733-76-8
• 化学式: C₂₅H₅₂O₄Si
• 分子量: 444.771
• InChiKey: ROROBLQMVYPIIA-OLKYXYMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  30
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R,6R)-3-(tert-butyldimethylsilyloxy)-6-[(1S)-1,2-dihydroxyethyl]-2-dodecyltetrahydropyran 、 叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 4.0h， 以98%的产率得到(2R,3R,6R)-3-(tert-butyldimethylsilyloxy)-6-[(1S)-2-tert-butyldimethylsilyloxy-1-hydroxyethyl]-2-dodecyltetrahydropyran
  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：

  (2R,3R,6R)-3-(tert-butyldimethylsilyloxy)-2-dodecyl-6-(1-ethenyl)tetrahydropyran 在 potassium osmate 、 potassium hexacyanoferrate(III) 、 甲基磺酰胺 、 AQN(DHQD)2 、 potassium carbonate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 22.0h， 以90%的产率得到(2R,3R,6R)-3-(tert-butyldimethylsilyloxy)-6-[(1S)-1,2-dihydroxyethyl]-2-dodecyltetrahydropyran
  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 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.