(3S)-3-[tert-butyl(dimethyl)silyl]oxy-3-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]propanenitrile | 1255764-11-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-3-[tert-butyl(dimethyl)silyl]oxy-3-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]propanenitrile
• CAS: 1255764-11-4
• 化学式: C₁₆H₂₉NO₃Si
• 分子量: 311.497
• InChiKey: ILEBLLVNAHOYHJ-IHRRRGAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  51.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S)-3-[tert-butyl(dimethyl)silyl]oxy-3-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]propanenitrile 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以77%的产率得到(S)-3-((tert-butyldimethylsilyl)oxy)-3-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)propanal
  参考文献：
  名称：

  (−)-Lytophilippine A: Synthesis of a C1−C18 Building Block

  摘要：

  The convergent enantioselective synthesis of a protected C1-C18 building block for the total synthesis of (-)-lytophilippine A was achieved. A catalytic asymmetric Gosteli-Claisen rearrangement and an Evans aldol reaction served as key C/C-connecting transformations during the assembling of the C1-C7 subunit (10 steps from 4, 29%). The synthesis of the C8-C18 segment was achieved utilizing D-galactose as inexpensive ex-chiral-pool starting material (15 steps, 15%). The merger of the subunits was accomplished by a remarkably efficient sequence consisting of esterification and ring-closing metathesis (five steps, 56%).

  DOI：

  10.1021/ol1023008
• 作为产物：
  描述：

  (3S)-3-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanenitrile 、 叔丁基二甲硅基三氟甲磺酸酯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以93%的产率得到(3S)-3-[tert-butyl(dimethyl)silyl]oxy-3-[(4S,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]propanenitrile
  参考文献：
  名称：

  (−)-Lytophilippine A: Synthesis of a C1−C18 Building Block

  摘要：

  The convergent enantioselective synthesis of a protected C1-C18 building block for the total synthesis of (-)-lytophilippine A was achieved. A catalytic asymmetric Gosteli-Claisen rearrangement and an Evans aldol reaction served as key C/C-connecting transformations during the assembling of the C1-C7 subunit (10 steps from 4, 29%). The synthesis of the C8-C18 segment was achieved utilizing D-galactose as inexpensive ex-chiral-pool starting material (15 steps, 15%). The merger of the subunits was accomplished by a remarkably efficient sequence consisting of esterification and ring-closing metathesis (five steps, 56%).

  DOI：

  10.1021/ol1023008

文献信息

• (−)-Lytophilippine A: Synthesis of a C1−C18 Building Block
  作者：Annika Gille、Martin Hiersemann

  DOI：10.1021/ol1023008

  日期：2010.11.19

  The convergent enantioselective synthesis of a protected C1-C18 building block for the total synthesis of (-)-lytophilippine A was achieved. A catalytic asymmetric Gosteli-Claisen rearrangement and an Evans aldol reaction served as key C/C-connecting transformations during the assembling of the C1-C7 subunit (10 steps from 4, 29%). The synthesis of the C8-C18 segment was achieved utilizing D-galactose as inexpensive ex-chiral-pool starting material (15 steps, 15%). The merger of the subunits was accomplished by a remarkably efficient sequence consisting of esterification and ring-closing metathesis (five steps, 56%).