(2R,2'R,5R,5'R)-5'-((1S,4S)-1,4-di(tert-butyldimethylsilyloxy)undecyl)octahydro-2,2'-bifuranyl-5-carbaldehyde | 1011298-68-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,2'R,5R,5'R)-5'-((1S,4S)-1,4-di(tert-butyldimethylsilyloxy)undecyl)octahydro-2,2'-bifuranyl-5-carbaldehyde
• 英文别名: (2R,5R)-5-[(2R,5R)-5-[(1S,4S)-1,4-bis[[tert-butyl(dimethyl)silyl]oxy]undecyl]oxolan-2-yl]oxolane-2-carbaldehyde
• CAS: 1011298-68-2
• 化学式: C₃₂H₆₄O₅Si₂
• 分子量: 585.028
• InChiKey: HEUOCSBODSVFJB-LEHZDZAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,2'R,5R,5'R)-5'-((1S,4S)-1,4-di(tert-butyldimethylsilyloxy)undecyl)octahydro-2,2'-bifuranyl-5-carbaldehyde 、 (+)-Ipc2B(烯丙基)硼烷 在 双氧水 、 三乙胺 作用下， 以 乙醚 、 甲醇 、 水 为溶剂， 生成 (R)-1-((2R,2'R,5R,5'R)-5'-((1S,4S)-1,4-di(tert-butyldimethylsilyloxy)undecyl)octahydro-2,2'-bifuranyl-5-yl)but-3-en-1-ol 、 (S)-1-((2R,2'R,5R,5'R)-5'-((1S,4S)-1,4-di(tert-butyldimethylsilyloxy)undecyl)octahydro-2,2'-bifuranyl-5-yl)but-3-en-1-ol
  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'-((1S,4S)-1,4-di(tert-butyldimethylsilyloxy)undecyl)octahydro-2,2'-bifuranyl-5-yl)-methanol 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到(2R,2'R,5R,5'R)-5'-((1S,4S)-1,4-di(tert-butyldimethylsilyloxy)undecyl)octahydro-2,2'-bifuranyl-5-carbaldehyde
  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.