(2S,4S)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylpentanoic acid | 1417795-86-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2S,4S)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylpentanoic acid
• CAS: 1417795-86-8
• 化学式: C₂₃H₃₂O₃Si
• 分子量: 384.591
• InChiKey: UHMZVBCFAQMCOO-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,4S)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylpentanoic acid 在 lithium aluminium tetrahydride 、 草酰氯 、 四丁基氟化铵 、 sodium hydride 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 异辛烷 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.83h， 生成 (2S,4R)-5-(4-methoxybenzyloxy)-2,4-dimethylpentanal
  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：

  (S)-3-(tert-butyldiphenylsilyloxy)-2-methylpropyl acetate 在 甲醇 、 lithium aluminium tetrahydride 、 草酰氯 、 potassium carbonate 、 二甲基亚砜 、 nickel dichloride 作用下， 以 甲醇 、 异辛烷 、 乙醚 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (2S,4S)-5-[tert-butyl(diphenyl)silyl]oxy-2,4-dimethylpentanoic acid
  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

文献信息

• Stereoselective syntheses of siphonarienal and siphonarienone
  作者：Supriya Ghanty、Chinta Krinda Suresh Kumar、B.V. Subba Reddy

  DOI：10.1016/j.tetasy.2015.07.001

  日期：2015.9

  The asymmetric total synthesis of marine polypropionate natural products siphonarienal and siphonarienone has been achieved from a common precursor 3. The key transformations of this synthesis are the diastereoselective oxidative kinetic resolution, Wittig olefination, Grignard reaction, and Evans asymmetric alkylation for the installation of a third stereogenic center of the target molecules from

  船用聚丙烯酸酯天然产物siphonarienal和siphonarienoneone的不对称全合成已从常见的前体3中获得。该合成的关键转变是非对映选择性氧化动力学拆分，Wittig烯烃化，Grignard反应和Evans不对称烷基化，用于从可商购的原材料中安装靶分子的第三个立体异构中心。
• Asymmetric total synthesis of (−)-rasfonin
  作者：Rajib Bhuniya、Samik Nanda

  DOI：10.1016/j.tet.2012.11.051

  日期：2013.1

  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.