(2E,4E,6S)-(2R,3R)-3,6-dihydro-2-((E,2S,4R)-4,6-dimethyloct-6-en-2-yl)-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate | 1417796-01-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2E,4E,6S)-(2R,3R)-3,6-dihydro-2-((E,2S,4R)-4,6-dimethyloct-6-en-2-yl)-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate
• 英文别名: [(2R,3R)-2-[(E,2S,4R)-4,6-dimethyloct-6-en-2-yl]-6-oxo-2,3-dihydropyran-3-yl] (2E,4E,6S)-8-[tert-butyl(diphenyl)silyl]oxy-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-4-methylocta-2,4-dienoate
• CAS: 1417796-01-0
• 化学式: C₅₇H₇₄O₆Si₂
• 分子量: 911.382
• InChiKey: PJNJKRYPWBKYPN-AJKOCZTASA-N

物化性质

• 沸点：
  843.8±65.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.06
• 重原子数：
  65
• 可旋转键数：
  23
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E,4E,6S)-(2R,3R)-3,6-dihydro-2-((E,2S,4R)-4,6-dimethyloct-6-en-2-yl)-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-4-methylocta-2,4-dienoate 在 pyridine hydrofluoride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以72%的产率得到(-)-(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 、 N,N-二甲基乙酰胺 、 2,4,6-三氯苯甲酰氯 、 lipase PS-D immobilized on diatomite 、 水 、 碘 、 铜 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hydroxide 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醚 、 甲苯 为溶剂， 反应 96.58h， 生成 (2E,4E,6S)-(2R,3R)-3,6-dihydro-2-((E,2S,4R)-4,6-dimethyloct-6-en-2-yl)-6-oxo-2H-pyran-3-yl 8-tert-butyldiphenylsilyloxy-6-(tert-butyldiphenylsilyloxy-methyl)-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

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.