(4S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methoxy-5-oxopentanoic acid | 958447-69-3

• 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: (4S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methoxy-5-oxopentanoic acid
• CAS: 958447-69-3
• 化学式: C₁₂H₂₄O₅Si
• 分子量: 276.405
• InChiKey: MBUANYNMZYTZSC-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methoxy-5-oxopentanoic acid 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  BF3·Et2O catalyzed diastereoselective nucleophilic reactions of 3-silyloxypiperidine N,O-acetal with silyl enol ether and application to the asymmetric synthesis of (+)-febrifugine

  摘要：

  The asymmetric BF3 center dot Et2O catalyzed nucleophilic reactions of 3-silyloxypiperidine N,O-acetal 10 with silyl enol ethers derived from ketones are described. (+)-Febrifugine 1, an antimalarial alkaloid, was successfully synthesized based on this nucleophilic substitution. In addition, N,O-acetal 10 was synthesized from L-benzyl glutamate in 11 steps. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.097
• 作为产物：
  描述：

  5-benzyl 1-methyl (S)-2-((tert-butyldimethylsilyl)oxy)pentanedioate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以83%的产率得到(4S)-4-[tert-butyl(dimethyl)silyl]oxy-5-methoxy-5-oxopentanoic acid
  参考文献：
  名称：

  BF3·Et2O catalyzed diastereoselective nucleophilic reactions of 3-silyloxypiperidine N,O-acetal with silyl enol ether and application to the asymmetric synthesis of (+)-febrifugine

  摘要：

  The asymmetric BF3 center dot Et2O catalyzed nucleophilic reactions of 3-silyloxypiperidine N,O-acetal 10 with silyl enol ethers derived from ketones are described. (+)-Febrifugine 1, an antimalarial alkaloid, was successfully synthesized based on this nucleophilic substitution. In addition, N,O-acetal 10 was synthesized from L-benzyl glutamate in 11 steps. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.097

文献信息

• BF3·Et2O catalyzed diastereoselective nucleophilic reactions of 3-silyloxypiperidine N,O-acetal with silyl enol ether and application to the asymmetric synthesis of (+)-febrifugine
  作者：Ru-Cheng Liu、Wei Huang、Jing-Yi Ma、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1016/j.tetlet.2009.04.097

  日期：2009.7

  The asymmetric BF3 center dot Et2O catalyzed nucleophilic reactions of 3-silyloxypiperidine N,O-acetal 10 with silyl enol ethers derived from ketones are described. (+)-Febrifugine 1, an antimalarial alkaloid, was successfully synthesized based on this nucleophilic substitution. In addition, N,O-acetal 10 was synthesized from L-benzyl glutamate in 11 steps. (C) 2009 Elsevier Ltd. All rights reserved.