(2S,3R,5S)-2-[(1S,3R)-4-[tert-butyl(diphenyl)silyl]oxy-1-hydroxy-3-methylbutyl]-5-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-3-ol | 1255763-58-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,5S)-2-[(1S,3R)-4-[tert-butyl(diphenyl)silyl]oxy-1-hydroxy-3-methylbutyl]-5-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-3-ol
• CAS: 1255763-58-6
• 化学式: C₃₂H₄₆O₆Si
• 分子量: 554.799
• InChiKey: MPTLSRUMZJSYBS-JBEDOFGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,5S)-2-[(1S,3R)-4-[tert-butyl(diphenyl)silyl]oxy-1-hydroxy-3-methylbutyl]-5-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-3-ol 、 以 二氯甲烷 为溶剂， 反应 3.5h， 以0.49 g的产率得到[(2S,3R,5S)-2-[(1S,3R)-4-[tert-butyl(diphenyl)silyl]oxy-1-hydroxy-3-methylbutyl]-5-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-3-yl] (2S,3S,4R,5S,6R)-3-[tert-butyl(dimethyl)silyl]oxy-4-[(4-methoxyphenyl)methoxy]-2,5,6-trimethyloct-7-enoate
  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：

  (1R,3S)-1-(3-((R)-3-((tert-butyldiphenylsilyl)oxy)-2-methylpropyl)oxiran-2-yl)-3-((4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)propane-1,3-diol 、 丙酮 在 D(+)-10-樟脑磺酸 作用下， 反应 0.75h， 以55%的产率得到(2S,3R,5S)-2-[(1S,3R)-4-[tert-butyl(diphenyl)silyl]oxy-1-hydroxy-3-methylbutyl]-5-[(4R,5S)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]oxolan-3-ol
  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%).