(5R,5aR,8S,8aS,8bS)-1,3-Dibenzyl-8b-hydroxy-5-hydroxymethyl-7-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione | 896141-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (5R,5aR,8S,8aS,8bS)-1,3-Dibenzyl-8b-hydroxy-5-hydroxymethyl-7-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione
• CAS: 896141-44-9
• 化学式: C₄₁H₅₃N₃O₇SSi
• 分子量: 760.039
• InChiKey: JDOLDTJSACTOLQ-IXKLOCLUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.65
• 重原子数：
  53.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  127.69
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (5R,5aR,8S,8aS,8bS)-1,3-Dibenzyl-8b-hydroxy-5-hydroxymethyl-7-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-octahydro-imidazo[4,5-e]isoindole-2,6-dione 在 N-氯代丁二酰亚胺 、 环己烯 作用下， 以78%的产率得到
  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 、 magnesium sulfate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 96.0h， 生成 (5R,5aR,8S,8aS,8bS)-1,3-Dibenzyl-8b-hydroxy-5-hydroxymethyl-7-(toluene-4-sulfonyl)-8-triisopropylsilanyloxymethyl-1,3,5,5a,7,8,8a,8b-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