tert-butyl (((2S,3S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-1,4-dioxan-2-yl)methoxy)dimethylsilane | 1015076-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (((2S,3S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-1,4-dioxan-2-yl)methoxy)dimethylsilane
• 英文别名: tert-butyl-[[(2S,3S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-[(E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]-1,4-dioxan-2-yl]methoxy]-dimethylsilane
• CAS: 1015076-52-4
• 化学式: C₂₃H₄₅BO₇Si
• 分子量: 472.503
• InChiKey: DXKDGSYNGJEKOR-OEKAXEONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl (((2S,3S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-1,4-dioxan-2-yl)methoxy)dimethylsilane 、 2,2-dimethyl-5-trifluoromethylsulfonyloxy-4H-(1,3)benzodioxin-4-one 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以54%的产率得到5-((E)-2-((2S,3S,5R,6R)-3-((tert-butyldimethylsilyloxy)methyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)vinyl)-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one
  参考文献：
  名称：

  A new synthesis of (−)-epipyriculol: a phytotoxic metabolite

  摘要：

  A convenient synthesis of the phytotoxic natural product epipyriculol has been accomplished in 17 steps from methyl L-tartrate. The synthetic strategy is based upon the use of a butanediacetal-protected scaffold as central core from which the alkenyl side chains were assembled. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.115
• 作为产物：
  描述：

  tert-butyl (((2S,3S,5R,6R)-2-ethynyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl)methoxy)dimethylsilane 、 频那醇硼烷 反应 24.0h， 以100%的产率得到tert-butyl (((2S,3S,5R,6R)-5,6-dimethoxy-5,6-dimethyl-3-((E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)-1,4-dioxan-2-yl)methoxy)dimethylsilane
  参考文献：
  名称：

  官能化丁二缩醛保护的1,2-二醇作为Pd催化交叉偶联反应的合适伴侣

  摘要：

  描述了一种合成包含手性1,2-二醇的二烯和烯炔的新方法。该策略基于Pd催化的一系列乙烯基和炔基不对称丁烷二缩醛保护的结构单元的交叉偶联反应。偶合后，除去保护基团得到所需的官能化的二烯和烯炔。

  DOI：

  10.1016/j.tet.2008.01.010

文献信息

• Functionalised butanediacetal-protected 1,2-diols as suitable partners for Pd-catalysed cross-coupling reactions
  作者：Antonio Leyva、Francesca E. Blum、Peter R. Hewitt、Steven V. Ley

  DOI：10.1016/j.tet.2008.01.010

  日期：2008.3

  A new method for the synthesis of dienes and enynes containing chiral 1,2-diols is described. The strategy is based on the Pd-catalysed cross-coupling reactions of a series of vinyl and alkynyl asymmetric butanediacetal-protected building blocks. After the coupling, removal of the protecting group leads to the desired functionalised dienes and enynes.

  描述了一种合成包含手性1,2-二醇的二烯和烯炔的新方法。该策略基于Pd催化的一系列乙烯基和炔基不对称丁烷二缩醛保护的结构单元的交叉偶联反应。偶合后，除去保护基团得到所需的官能化的二烯和烯炔。
• A new synthesis of (−)-epipyriculol: a phytotoxic metabolite
  作者：Antonio Leyva、Francesca E. Blum、Steven V. Ley

  DOI：10.1016/j.tet.2008.01.115

  日期：2008.5

  A convenient synthesis of the phytotoxic natural product epipyriculol has been accomplished in 17 steps from methyl L-tartrate. The synthetic strategy is based upon the use of a butanediacetal-protected scaffold as central core from which the alkenyl side chains were assembled. (C) 2008 Elsevier Ltd. All rights reserved.