(4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one | 1417803-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one
• 英文别名: (4R,5S)-5-[(2S)-3-[tert-butyl(diphenyl)silyl]oxy-2-methylpropyl]-4-prop-2-enyloxolan-2-one
• CAS: 1417803-54-3
• 化学式: C₂₇H₃₆O₃Si
• 分子量: 436.667
• InChiKey: WIJNWGQERGHMGN-FBLLAGFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 六甲基磷酰三胺 、 Hoveyda-Grubbs catalyst second generation 、 二苯基二硒醚 、 potassium tert-butylate 、 四丁基氟化铵 、 戴斯-马丁氧化剂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 25.49h， 生成 xanthatin
  参考文献：
  名称：

  Asymmetric total syntheses of xanthatin and 11,13-dihydroxanthatin using a stereocontrolled conjugate allylation to γ-butenolide

  摘要：

  The stereocontrolled conjugate allylation to an optically pure gamma-butenolide provided direct and reliable access to a trans-fused series of xanthanolide sesquiterpenoids and allowed for the enantioselective total syntheses of xanthatin and 11,13-dihydroxanthatin to be efficiently achieved. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.077
• 作为产物：
  描述：

  (5S)-5-[(2S)-3-(tert-butyldiphenylsiloxy)-2-methylpropyl]furan-2(5H)-one 、 lithium;but-1-ene;copper(1+);cyanide 以 四氢呋喃 为溶剂， 以21%的产率得到(4R,5S)-4-allyl-5-[(2S)-3-tert-butyldiphenylsiloxy-2-methylpropyl]dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Asymmetric total syntheses of xanthatin and 11,13-dihydroxanthatin using a stereocontrolled conjugate allylation to γ-butenolide

  摘要：

  The stereocontrolled conjugate allylation to an optically pure gamma-butenolide provided direct and reliable access to a trans-fused series of xanthanolide sesquiterpenoids and allowed for the enantioselective total syntheses of xanthatin and 11,13-dihydroxanthatin to be efficiently achieved. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.077

文献信息

• Asymmetric total syntheses of xanthatin and 11,13-dihydroxanthatin using a stereocontrolled conjugate allylation to γ-butenolide
  作者：Kenji Matsumoto、Kuniyoshi Koyachi、Mitsuru Shindo

  DOI：10.1016/j.tet.2012.11.077

  日期：2013.1

  The stereocontrolled conjugate allylation to an optically pure gamma-butenolide provided direct and reliable access to a trans-fused series of xanthanolide sesquiterpenoids and allowed for the enantioselective total syntheses of xanthatin and 11,13-dihydroxanthatin to be efficiently achieved. (C) 2012 Elsevier Ltd. All rights reserved.