[(2R,5R)-5-[(2R,5R)-5-[(1S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyundec-2-ynyl]oxolan-2-yl]oxolan-2-yl]methyl benzoate | 1011298-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(2R,5R)-5-[(2R,5R)-5-[(1S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyundec-2-ynyl]oxolan-2-yl]oxolan-2-yl]methyl benzoate
• CAS: 1011298-74-0
• 化学式: C₃₃H₅₂O₆Si
• 分子量: 572.858
• InChiKey: VFUCNHMHLOFHHC-MDDVVAPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.05
• 重原子数：
  40
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2R,5R)-5-[(2R,5R)-5-[(1S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyundec-2-ynyl]oxolan-2-yl]oxolan-2-yl]methyl benzoate 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以100%的产率得到((2R,2'R,5R,5'R)-5'-((1S,4S)-1,4-di(tert-butyldimethylsilyloxy)undec-2-ynyl)octahydro-2,2'-bifuranyl-5-yl)methyl benzoate
  参考文献：
  名称：

  Total synthesis of 27-hydroxy-bullatacin and its C-15 epimer, and studies on their inhibitory effect on bovine heart mitochondrial complex I functions

  摘要：

  The total synthesis of 27-hydroxybullatacin and its C-15 epimer has been achieved using rhenium(VII) oxides-mediated and Co(modp)(2)-catalyzed oxidative cyclization (OC), diastereoselective alkynylation, Brown's enantioselective allylboration, and Grubbs' cross metathesis as the key reactions. The inhibitory effect of these compounds on the complex I function, as determined by using bovine submitochondrial particles, was in low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.089
• 作为产物：
  描述：

  ((2R,2'R,5R,5'R)-5'-formyloctahydro-2,2'-bifuranyl-5-yl)methyl benzoate 、 (S)-O-(tert-Butyldimethylsilyl)-dec-1-yn-3-ol 在 正丁基锂 作用下， 以 乙醚 、 正己烷 、 甲苯 为溶剂， 反应 1.0h， 以86%的产率得到[(2R,5R)-5-[(2R,5R)-5-[(1S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-1-hydroxyundec-2-ynyl]oxolan-2-yl]oxolan-2-yl]methyl benzoate
  参考文献：
  名称：

  Total synthesis of 27-hydroxy-bullatacin and its C-15 epimer, and studies on their inhibitory effect on bovine heart mitochondrial complex I functions

  摘要：

  The total synthesis of 27-hydroxybullatacin and its C-15 epimer has been achieved using rhenium(VII) oxides-mediated and Co(modp)(2)-catalyzed oxidative cyclization (OC), diastereoselective alkynylation, Brown's enantioselective allylboration, and Grubbs' cross metathesis as the key reactions. The inhibitory effect of these compounds on the complex I function, as determined by using bovine submitochondrial particles, was in low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.089

文献信息

• Total synthesis of 27-hydroxy-bullatacin and its C-15 epimer, and studies on their inhibitory effect on bovine heart mitochondrial complex I functions
  作者：Zhiyong Chen、Subhash C. Sinha

  DOI：10.1016/j.tet.2007.11.089

  日期：2008.2

  The total synthesis of 27-hydroxybullatacin and its C-15 epimer has been achieved using rhenium(VII) oxides-mediated and Co(modp)(2)-catalyzed oxidative cyclization (OC), diastereoselective alkynylation, Brown's enantioselective allylboration, and Grubbs' cross metathesis as the key reactions. The inhibitory effect of these compounds on the complex I function, as determined by using bovine submitochondrial particles, was in low nanomolar range. (C) 2007 Elsevier Ltd. All rights reserved.