(3S)-3-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanenitrile | 1255764-51-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S)-3-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanenitrile
• CAS: 1255764-51-2
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: GMFYRGNUIKTGPH-XHNCKOQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  sodium cyanide 、 (S)-2-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate 在 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以85%的产率得到(3S)-3-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxypropanenitrile
  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