(S,2E,4E)-8-(tert-butyldiphenylsilyloxy)-6-((tert-butyldiphenylsilyloxy)methyl)-4-methylocta-2,4-dienoic acid | 1417796-04-3

• 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: (S,2E,4E)-8-(tert-butyldiphenylsilyloxy)-6-((tert-butyldiphenylsilyloxy)methyl)-4-methylocta-2,4-dienoic acid
• 英文别名: (2E,4E,6S)-8-[tert-butyl(diphenyl)silyl]oxy-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-methylocta-2,4-dienoic acid
• CAS: 1417796-04-3
• 化学式: C₄₂H₅₂O₄Si₂
• 分子量: 677.043
• InChiKey: MZAIYPHLCSYTQD-IPLYBHJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.73
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S,2E,4E)-8-(tert-butyldiphenylsilyloxy)-6-((tert-butyldiphenylsilyloxy)methyl)-4-methylocta-2,4-dienoic acid 在 咪唑 、 N,N-二甲基乙酰胺 、 pyridine hydrofluoride 、 2,4,6-三氯苯甲酰氯 、 水 、 碘 、 铜 、 三乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 89.5h， 生成 (-)-(S,2E,4E)-((2R,3R)-2-((2S,4R,E)-4,6-dimethyloct-6-en-2-yl)-6-oxo-3,6-dihydro-2H-pyran-3-yl) 8-hydroxy-6-(hydroxymethyl)-4-methylocta-2,4-dienoate
  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：

  2-(2-(tert-butyldiphenylsilyloxy)ethyl)propane-1,3-diol 在 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 草酰氯 、 lipase PS-Amano 、 水 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 二甲基亚砜 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醚 为溶剂， 反应 79.08h， 生成 (S,2E,4E)-8-(tert-butyldiphenylsilyloxy)-6-((tert-butyldiphenylsilyloxy)methyl)-4-methylocta-2,4-dienoic 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

• 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.