triethyl-[(2R)-1-triethylsilyloxybutan-2-yl]oxysilane | 611228-19-4

• 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: triethyl-[(2R)-1-triethylsilyloxybutan-2-yl]oxysilane
• CAS: 611228-19-4
• 化学式: C₁₆H₃₈O₂Si₂
• 分子量: 318.648
• InChiKey: DGUGRZLFXRQGHL-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  triethyl-[(2R)-1-triethylsilyloxybutan-2-yl]oxysilane 在 chromium dichloride 、 正丁基锂 、 甲基锂 、 dipyridine chromium trioxide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 methyl 8-[(1R,2S,3S)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxo-2-[(E,3R)-3-triethylsilyloxypent-1-enyl]cyclopentyl]octanoate
  参考文献：
  名称：

  First total synthesis of the E type I phytoprostanes

  摘要：

  The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxy-cyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.042
• 作为产物：
  描述：

  (R)-1,2-丁二醇 、 三乙基氯硅烷 在 咪唑 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到triethyl-[(2R)-1-triethylsilyloxybutan-2-yl]oxysilane
  参考文献：
  名称：

  First total synthesis of the E type I phytoprostanes

  摘要：

  The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxy-cyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.042

文献信息

• Trihydroxy polyunsaturated eicosanoids
  申请人：——

  公开号：US20030236423A1

  公开（公告）日：2003-12-25

  The invention features methods for the preparation of naturally occurring trihydroxy polyunsaturated eicosanoids and their structural analogs. The invention further provides new derivatives of trihydroxy polyunsaturated eicosanoids that can be prepared according to these methods. The invention also provides trihydroxy polyunsaturated eicosanoids and their use in pharmaceutical compositions.

  该发明涉及制备天然存在的三羟基多不饱和二十碳五烯酸类化合物及其结构类似物的方法。该发明进一步提供了可以根据这些方法制备的三羟基多不饱和二十碳五烯酸类化合物的新衍生物。该发明还提供了三羟基多不饱和二十碳五烯酸类化合物及其在制药组合物中的用途。
• First total synthesis of the E type I phytoprostanes
  作者：Ana R. Rodrı́guez、Bernd W. Spur

  DOI：10.1016/j.tetlet.2003.08.042

  日期：2003.9

  The first total synthesis of two E type I phytoprostanes from furan, azelaic acid monomethyl ester and rac-1,2-epoxybutane is described. The key features of our synthetic strategy encompass an enzymatic kinetic resolution of a hydroxy-cyclopentenone, a Co-salen hydrolytic kinetic resolution of a terminal epoxide and a tandem conjugate addition/diastereoselective protonation sequence to construct the protected phytoprostanes. Mild cleavage of the silyl protective groups followed by enzymatic ester hydrolysis afforded the free E-type phytoprostanes. (C) 2003 Elsevier Ltd. All rights reserved.