(R)-2-{(4S,5R)-5-[10-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-decyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(2-methoxy-ethoxymethoxy)-ethanol | 185612-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-{(4S,5R)-5-[10-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-decyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(2-methoxy-ethoxymethoxy)-ethanol
• 英文别名: (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)ethanol
• CAS: 185612-34-4
• 化学式: C₂₆H₅₀O₈
• 分子量: 490.678
• InChiKey: FSGLWVRUPSWICH-YCAMKHIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  34
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (R)-2-{(4S,5R)-5-[10-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-decyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(2-methoxy-ethoxymethoxy)-ethanol 在 N-氯代丁二酰亚胺 、 二甲基硫 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.58h， 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
• 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 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以97%的产率得到(R)-2-{(4S,5R)-5-[10-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-decyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-2-(2-methoxy-ethoxymethoxy)-ethanol
  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).