methyl (2S)-2-[(4R,6R)-6-[(2R,3R)-3-[2-[(Z,3S,5R,7R,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-methoxy-3-(methoxymethoxy)-7-[(4-methoxyphenyl)methoxy]-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)acetate | 1092070-86-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2S)-2-[(4R,6R)-6-[(2R,3R)-3-[2-[(Z,3S,5R,7R,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-methoxy-3-(methoxymethoxy)-7-[(4-methoxyphenyl)methoxy]-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)acetate
• CAS: 1092070-86-4
• 化学式: C₆₅H₁₀₄O₁₄S₂Si₂
• 分子量: 1229.84
• InChiKey: AWDZGHFJYNBYMX-ISHLIERCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.05
• 重原子数：
  83
• 可旋转键数：
  37
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  199
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[(4R,6R)-6-[(2R,3R)-3-[2-[(Z,3S,5R,7R,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-methoxy-3-(methoxymethoxy)-7-[(4-methoxyphenyl)methoxy]-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)acetate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以91%的产率得到
  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
• 作为产物：
  描述：

  methyl (2S)-2-[(4R,6S)-6-[(2R)-2-methoxy-3-oxopropyl]-2,2-dimethyl-1,3-dioxan-4-yl]-2-(2-trimethylsilylethoxymethoxy)acetate 、 tert-butyl-[(Z,2R,5R,7R,9S)-10-(1,3-dithian-2-yl)-2-ethyl-7-methoxy-9-(methoxymethoxy)-5-[(4-methoxyphenyl)methoxy]-4,10-dimethylundec-3-enoxy]-diphenylsilane 在 六甲基磷酰三胺 、 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 4.5h， 以40%的产率得到methyl (2S)-2-[(4R,6R)-6-[(2R,3R)-3-[2-[(Z,3S,5R,7R,10R)-10-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-methoxy-3-(methoxymethoxy)-7-[(4-methoxyphenyl)methoxy]-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)acetate
  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).