(1S)-1-[(2S,3R)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]prop-2-en-1-ol | 1141379-56-7

• 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: (1S)-1-[(2S,3R)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]prop-2-en-1-ol
• CAS: 1141379-56-7
• 化学式: C₂₂H₂₈O₃Si
• 分子量: 368.548
• InChiKey: NZJHOJJBYPLTIK-HBMCJLEFSA-N

物化性质

• 沸点：
  440.2±31.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-1-[(2S,3R)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]prop-2-en-1-ol 、 丙烯酸乙酯 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以60%的产率得到C₂₅H₃₂O₅Si
  参考文献：
  名称：

  Diastereoselective construction of substituted tetrahydropyrans using an intramolecular oxy-Michael strategy

  摘要：

  The highly diastereoselective construction of Substituted tetrahydropyrans, a common core segment (C3-C10) of the thiomarinols and the pseudomonic acid antibiotics, has been accomplished using the intramolecular oxy-Michael reaction under both basic and high-pressure conditions followed by regio- and stereoselective epoxide opening with acetylide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.084
• 作为产物：
  描述：

  (1R)-1-[(2S,3R)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]prop-2-en-1-ol 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 对硝基苯甲酸 、 lithium hydroxide monohydrate 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 30.0h， 以54%的产率得到(1S)-1-[(2S,3R)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]prop-2-en-1-ol
  参考文献：
  名称：

  Diastereoselective construction of substituted tetrahydropyrans using an intramolecular oxy-Michael strategy

  摘要：

  The highly diastereoselective construction of Substituted tetrahydropyrans, a common core segment (C3-C10) of the thiomarinols and the pseudomonic acid antibiotics, has been accomplished using the intramolecular oxy-Michael reaction under both basic and high-pressure conditions followed by regio- and stereoselective epoxide opening with acetylide. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.084

文献信息

• Diastereoselective construction of substituted tetrahydropyrans using an intramolecular oxy-Michael strategy
  作者：Fumika Yakushiji、Jacques Maddaluno、Masahiro Yoshida、Kozo Shishido

  DOI：10.1016/j.tetlet.2009.01.084

  日期：2009.4

  The highly diastereoselective construction of Substituted tetrahydropyrans, a common core segment (C3-C10) of the thiomarinols and the pseudomonic acid antibiotics, has been accomplished using the intramolecular oxy-Michael reaction under both basic and high-pressure conditions followed by regio- and stereoselective epoxide opening with acetylide. (C) 2009 Elsevier Ltd. All rights reserved.