2,2-Dimethyl-propionic acid (5R,5aS,8S,8aS)-3-(3,4-dimethoxy-benzyl)-2,6-dioxo-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,2,3,4,5,5a,6,7,8,8a-decahydro-imidazo[4,5-e]isoindol-5-ylmethyl ester | 896141-06-3

• 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: 2,2-Dimethyl-propionic acid (5R,5aS,8S,8aS)-3-(3,4-dimethoxy-benzyl)-2,6-dioxo-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,2,3,4,5,5a,6,7,8,8a-decahydro-imidazo[4,5-e]isoindol-5-ylmethyl ester
• CAS: 896141-06-3
• 化学式: C₅₀H₆₉N₃O₁₁S₂Si
• 分子量: 980.329
• InChiKey: LKZFSQZQFDKHNQ-LFVDYCRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.06
• 重原子数：
  67.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  169.51
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (5R,5aS,8S,8aS)-3-(3,4-dimethoxy-benzyl)-2,6-dioxo-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,2,3,4,5,5a,6,7,8,8a-decahydro-imidazo[4,5-e]isoindol-5-ylmethyl ester 在 二甲基二环氧乙烷 、 magnesium sulfate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 2,2-dimethyl-propionic acid 3-(3,4-dimethoxy-benzyl)-8b-hydroxy-2,6-dioxo-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,2,3,5,5a,6,7,8,8a,8b-decahydro-imidazo[4,5-e]isoindol-5-ylmethyl ester
  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 、 三乙胺 、 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 1.0h， 生成 2,2-Dimethyl-propionic acid (5R,5aS,8S,8aS)-3-(3,4-dimethoxy-benzyl)-2,6-dioxo-7-(toluene-4-sulfonyl)-1-[2-(toluene-4-sulfonyl)-ethyl]-8-triisopropylsilanyloxymethyl-1,2,3,4,5,5a,6,7,8,8a-decahydro-imidazo[4,5-e]isoindol-5-ylmethyl ester
  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