(2S)-2-[(4R,6R)-6-[(2R,3R)-3-[2-[(Z,3S,5R,7S,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-7-hydroxy-5-methoxy-3-(methoxymethoxy)-2,8-dimethyldodec-8-en-2-yl]-1,3-dithian-2-yl]-3-hydroxy-2-methoxypropyl]-2,2-dimethyl-1,3-dioxan-4-yl]-2-(2-trimethylsilylethoxymethoxy)acetic acid | 1092070-91-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (2S)-2-[(4R,6R)-6-[(2R,3R)-3-[2-[(Z,3S,5R,7S,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-7-hydroxy-5-methoxy-3-(methoxymethoxy)-2,8-dimethyldodec-8-en-2-yl]-1,3-dithian-2-yl]-3-hydroxy-2-methoxypropyl]-2,2-dimethyl-1,3-dioxan-4-yl]-2-(2-trimethylsilylethoxymethoxy)acetic acid
• CAS: 1092070-91-1
• 化学式: C₅₆H₉₄O₁₃S₂Si₂
• 分子量: 1095.66
• InChiKey: HASSRPWQNDVKNA-YJSHZEDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.73
• 重原子数：
  73
• 可旋转键数：
  32
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  211
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 (2S)-2-[(4R,6R)-6-[(2R,3R)-3-[2-[(Z,3S,5R,7S,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-7-hydroxy-5-methoxy-3-(methoxymethoxy)-2,8-dimethyldodec-8-en-2-yl]-1,3-dithian-2-yl]-3-hydroxy-2-methoxypropyl]-2,2-dimethyl-1,3-dioxan-4-yl]-2-(2-trimethylsilylethoxymethoxy)acetic acid 、
  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).