(5R,5aS,8S,8aS)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione | 896141-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (5R,5aS,8S,8aS)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione
• CAS: 896141-39-2
• 化学式: C₄₂H₅₅N₃O₉S₂Si
• 分子量: 838.131
• InChiKey: CTRNRZYOPBAIEE-KXTHTEOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  57.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  154.21
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  (5R,5aS,8S,8aS)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione 在 N-氯代丁二酰亚胺 、 sodium naphthalenide 、 magnesium sulfate 、 环己烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-8-triisopropylsilanyloxymethyl-1,3,7,8-tetrahydro-imidazo[4,5-e]isoindole-2,6-dione
  参考文献：
  名称：

  A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal

  摘要：

  Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.068
• 作为产物：
  描述：

  L-焦谷氨酸甲酯 在 咪唑 、 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 sodium hexamethyldisilazane 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 19.0h， 生成 (5R,5aS,8S,8aS)-5-Hydroxymethyl-3-(4-methoxy-benzyl)-1,7-bis-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,4,5,5a,7,8,8a-octahydro-imidazo[4,5-e]isoindole-2,6-dione
  参考文献：
  名称：

  A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal

  摘要：

  Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.068