ethyl (E,4R)-4-[(4S,5R)-5-[(11R)-11,12-dihydroxydodecyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-(2-methoxyethoxymethoxy)but-2-enoate | 185612-36-6

• 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: ethyl (E,4R)-4-[(4S,5R)-5-[(11R)-11,12-dihydroxydodecyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-(2-methoxyethoxymethoxy)but-2-enoate
• CAS: 185612-36-6
• 化学式: C₂₇H₅₀O₉
• 分子量: 518.689
• InChiKey: IXGBFCWGJCNKJZ-VXGJNJRNSA-N

物化性质

• 沸点：
  609.8±55.0 °C(predicted)
• 密度：
  1.056±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  36
• 可旋转键数：
  23
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  原乙酸三乙酯 、 ethyl (E,4R)-4-[(4S,5R)-5-[(11R)-11,12-dihydroxydodecyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-(2-methoxyethoxymethoxy)but-2-enoate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以84%的产率得到ethyl (E,4R)-4-[(4S,5R)-5-[(11R)-11-acetyloxy-12-bromododecyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-(2-methoxyethoxymethoxy)but-2-enoate
  参考文献：
  名称：

  Short Synthesis of (+)-Aspicilin via Asymmetric Hexahydroxylation of a Triene

  摘要：

  Asymmetric synthesis of the 18-membered lichen macrolide (+)-aspicilin has been achieved in 14 steps and 11% overall yield, starting from an achiral hydrocarbon, (3E)-hexadeca-1,3,15-triene. All four stereogenic carbinol centers have been introduced by three Sharpless asymmetric dihydroxylation (AD) reactions, using both AD-mix-beta and AD-mix-alpha to produce the hexol with very high regio- and enantioselectivity (epimeric excess of 88% at position 2, 96% at positions 3 and 4, and 86% at position 15).

  DOI：

  10.1021/jo00084a006
• 作为产物：
  描述：

  tert-butyl-[(2R)-2-[(4S,5R)-5-[10-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]decyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(2-methoxyethoxymethoxy)ethoxy]-dimethylsilane 在 N-氯代丁二酰亚胺 、 二甲基硫 、 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.58h， 生成 ethyl (E,4R)-4-[(4S,5R)-5-[(11R)-11,12-dihydroxydodecyl]-2,2-dimethyl-1,3-dioxolan-4-yl]-4-(2-methoxyethoxymethoxy)but-2-enoate
  参考文献：
  名称：

  Short Synthesis of (+)-Aspicilin via Asymmetric Hexahydroxylation of a Triene

  摘要：

  Asymmetric synthesis of the 18-membered lichen macrolide (+)-aspicilin has been achieved in 14 steps and 11% overall yield, starting from an achiral hydrocarbon, (3E)-hexadeca-1,3,15-triene. All four stereogenic carbinol centers have been introduced by three Sharpless asymmetric dihydroxylation (AD) reactions, using both AD-mix-beta and AD-mix-alpha to produce the hexol with very high regio- and enantioselectivity (epimeric excess of 88% at position 2, 96% at positions 3 and 4, and 86% at position 15).

  DOI：

  10.1021/jo00084a006

文献信息

• Short Synthesis of (+)-Aspicilin via Asymmetric Hexahydroxylation of a Triene
  作者：Subhash C. Sinha、Ehud Keinan

  DOI：10.1021/jo00084a006

  日期：1994.3

  Asymmetric synthesis of the 18-membered lichen macrolide (+)-aspicilin has been achieved in 14 steps and 11% overall yield, starting from an achiral hydrocarbon, (3E)-hexadeca-1,3,15-triene. All four stereogenic carbinol centers have been introduced by three Sharpless asymmetric dihydroxylation (AD) reactions, using both AD-mix-beta and AD-mix-alpha to produce the hexol with very high regio- and enantioselectivity (epimeric excess of 88% at position 2, 96% at positions 3 and 4, and 86% at position 15).