2-epi-peloruside A | 1092070-53-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 2-epi-peloruside A
• 英文别名: (1R,3R,4R,7S,9S,11S,13R,14R,15R)-4,11,13,14-tetrahydroxy-7-[(Z,4R)-4-(hydroxymethyl)hex-2-en-2-yl]-3,9,15-trimethoxy-12,12-dimethyl-6,17-dioxabicyclo[11.3.1]heptadecan-5-one
• CAS: 1092070-53-5
• 化学式: C₂₇H₄₈O₁₁
• 分子量: 548.672
• InChiKey: NETARJWZTMGMRM-ZIYQPZSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  164
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (1R,3R,4R,7S,9R,11S,13R,14R,15R)-7-((R,Z)-4-(((tert-butyldiphenylsilyl)oxy)methyl)hex-2-en-2-yl)-13,14-dihydroxy-3,9,15-trimethoxy-11-(methoxymethoxy)-12,12-dimethyl-4-((2-(trimethylsilyl)ethoxy)methoxy)-6,17-dioxabicyclo[11.3.1]heptadecan-5-one 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以66%的产率得到2-epi-peloruside A
  参考文献：
  名称：

  Total Synthesis of (−)-2-epi-Peloruside A

  摘要：

  A convergent synthesis of (-)-2-epi-peloruside A has been achieved. Highlights include implementation of multicomponent type I anion relay chemistry (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (-)-2-epi-peloruside A via an unexpected epimerization at C(2).

  DOI：

  10.1021/ol8019132

文献信息

• Total Synthesis of (−)-2-<i>epi</i>-Peloruside A
  作者：Amos B. Smith、Jason M. Cox、Noriyuki Furuichi、Craig S. Kenesky、Junying Zheng、Onur Atasoylu、William M. Wuest

  DOI：10.1021/ol8019132

  日期：2008.12.18

  A convergent synthesis of (-)-2-epi-peloruside A has been achieved. Highlights include implementation of multicomponent type I anion relay chemistry (ARC) to unite 2-TBS-1,3-dithiane with two epoxides to construct the eastern hemisphere, a late-stage dithiane union to secure the complete, fully functionalized carbon backbone, and Yamaguchi macrolactonization, which led to (-)-2-epi-peloruside A via an unexpected epimerization at C(2).