((2S,3R,4R)-1-(benzyloxy)-2,4,6-trimethylhept-5-en-3-yloxy)(tert-butyl)dimethylsilane | 474095-65-3

• 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: ((2S,3R,4R)-1-(benzyloxy)-2,4,6-trimethylhept-5-en-3-yloxy)(tert-butyl)dimethylsilane
• CAS: 474095-65-3
• 化学式: C₂₃H₄₀O₂Si
• 分子量: 376.655
• InChiKey: XKPRAYYXRQJHHB-RZUBCFFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  26.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ((2S,3R,4R)-1-(benzyloxy)-2,4,6-trimethylhept-5-en-3-yloxy)(tert-butyl)dimethylsilane 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙醇 、 正己烷 为溶剂， 以99%的产率得到(2S,3R,4R)-3-(tert-butyldimethylsilyloxy)-2,4,6-trimethylheptan-1-ol
  参考文献：
  名称：

  Asymmetric Catalysis Route to anti,anti Stereotriads, Illustrated by Applications

  摘要：

  A short sequence based on asymmetric catalysis, chirality transfer, and an optimized carbometallation protocol gave an anti,anti stereotriad building block in six steps. Both enantiomers of the chirality source, N-methyl ephedrine, are inexpensive, and the auxiliary is recoverable. In one chiral series, the building block was converted to the "B-2" intermediate in Miyashita's synthesis of scytophycin C; in the enantiomeric series, it was converted to a key intermediate for aplyronine A and to the polyketide "cap" for the callipeltins.

  DOI：

  10.1021/ol702989g
• 作为产物：
  描述：

  (R)-3-(benzyloxy)-2-methylpropan-1-ol 在 (+)-Ipc₂BOMe 、 四氧化锇 、 正丁基锂 、 草酰氯 、 二甲基亚砜 、 N-甲基吗啉氧化物 、 高碘酸 、 三乙胺 作用下， 反应 32.25h， 生成 ((2S,3R,4R)-1-(benzyloxy)-2,4,6-trimethylhept-5-en-3-yloxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Stereoselective synthesis of (2R,3R,4R)-3-hydroxy-2,4,6-trimethylheptanoic acid and determination of the absolute stereochemistry of the natural product from callipeltin A

  摘要：

  A revised stereostructure of 3-hydroxy-2,4,6-trimethylheptanoic acid, the beta-hydroxy acid that acylates the N-terminus of callipeltin A. is proposed on the basis of analysis of J-coupling in the H-1 NMR spectrum of the acetonide derivative obtained front the acid hydrolysate of callipeltin A. The proposed Structure was definitively confirmed by enantioselective synthesis. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00328-2