(2R,3S,4R)-3,4-dimethylhex-5-ene-1,2-diol | 1255763-86-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,3S,4R)-3,4-dimethylhex-5-ene-1,2-diol
• CAS: 1255763-86-0
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: UTHXMTOTGMMHRN-CSMHCCOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-甲氧基苯甲醛二甲缩醛 、 (2R,3S,4R)-3,4-dimethylhex-5-ene-1,2-diol 在 D(+)-10-樟脑磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以80%的产率得到
  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：

  在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(2R,3S,4R)-3,4-dimethylhex-5-ene-1,2-diol
  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%).