((2S,4R)-4-((4-methoxybenzyloxy)methyl)-2-methylpentyloxy)(tert-butyl)diphenylsilane | 1417795-87-9

• 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,4R)-4-((4-methoxybenzyloxy)methyl)-2-methylpentyloxy)(tert-butyl)diphenylsilane
• CAS: 1417795-87-9
• 化学式: C₃₁H₄₂O₃Si
• 分子量: 490.758
• InChiKey: LBAMDEUCDYADEY-FTJBHMTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  35.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ((2S,4R)-4-((4-methoxybenzyloxy)methyl)-2-methylpentyloxy)(tert-butyl)diphenylsilane 在 manganese(IV) oxide 、 正丁基锂 、 草酰氯 、 四丁基氟化铵 、 L-Selectride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.08h， 生成 (1R,2S,4R)-5-(4-methoxybenzyloxy)-1-(furan-2-yl)-2,4-dimethylpentan-1-ol
  参考文献：
  名称：

  Asymmetric total synthesis of (−)-rasfonin

  摘要：

  An efficient chemoenzymatic asymmetric synthesis of pyranone containing natural product (-)-rasfonin is presented here. Enantioselective enzymatic desymmetrization (EED) and a unique Gluconobacter oxydans mediated oxidative kinetic resolution (OKR) have been successfully employed to install three stereocenters (C-6', C-7, and C-9) of the target molecule. Stereoselective Achmatowicz reaction of a properly decorated furyl nucleus led to the core pyranone structure of rasfonin. At the late stage of the synthesis Negishi coupling has been used to complete the synthesis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.051
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 异辛烷 、 乙醚 为溶剂， 反应 8.0h， 生成 ((2S,4R)-4-((4-methoxybenzyloxy)methyl)-2-methylpentyloxy)(tert-butyl)diphenylsilane
  参考文献：
  名称：

  Asymmetric total synthesis of (−)-rasfonin

  摘要：

  An efficient chemoenzymatic asymmetric synthesis of pyranone containing natural product (-)-rasfonin is presented here. Enantioselective enzymatic desymmetrization (EED) and a unique Gluconobacter oxydans mediated oxidative kinetic resolution (OKR) have been successfully employed to install three stereocenters (C-6', C-7, and C-9) of the target molecule. Stereoselective Achmatowicz reaction of a properly decorated furyl nucleus led to the core pyranone structure of rasfonin. At the late stage of the synthesis Negishi coupling has been used to complete the synthesis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.051