(1S,5S,8aS,8bR)-5-Dimethylcarbamoylmethoxy-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester | 198402-12-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (1S,5S,8aS,8bR)-5-Dimethylcarbamoylmethoxy-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester
• CAS: 198402-12-9
• 化学式: C₂₈H₃₈N₂O₆
• 分子量: 498.62
• InChiKey: RZWBUCWYGBDJRZ-GZPGGTCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  96.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1S,5S,8aS,8bR)-5-Dimethylcarbamoylmethoxy-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 异丙醇 为溶剂， 生成 、 sodium;(1S,5S,8aS,8bR)-5-[2-(dimethylamino)-2-oxoethoxy]-1-[(1R)-1-hydroxyethyl]-2-oxo-5,6,7,8,8a,8b-hexahydro-1H-azeto[1,2-b]isoindole-4-carboxylate
  参考文献：
  名称：

  The synthesis of 4-aminocarbonylmethoxy trinems

  摘要：

  The synthesis of 4-aminocarbonylmethoxy trinems was accomplished through Lewis acid catalysed opening of an epoxide intermediate with allyl glycolate, followed by deallylation, activation of the free acid via the 2-pyridyl thiolester and reaction with a series of trimethylsilylamines. An alternative route involving a rhodium-catalysed diazoacetate insertion was also successfully exploited. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01053-3
• 作为产物：
  描述：

  [(1S,2S,3R)-3-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-(di-tert-butyl-hydroxy-silanyloxy)-cyclohexyloxy]-acetic acid allyl ester 在 四(三苯基膦)钯 、 草酰氯 、 四丁基氟化铵 、 四丁基溴化铵 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 对苯二酚 、 三苯基膦 、 cesium fluoride 、 亚磷酸三乙酯 、 sodium 2-ethylhexanoic acid 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 37.17h， 生成 (1S,5S,8aS,8bR)-5-Dimethylcarbamoylmethoxy-1-((R)-1-hydroxy-ethyl)-2-oxo-1,2,5,6,7,8,8a,8b-octahydro-azeto[2,1-a]isoindole-4-carboxylic acid 4-tert-butyl-benzyl ester
  参考文献：
  名称：

  The synthesis of 4-aminocarbonylmethoxy trinems

  摘要：

  The synthesis of 4-aminocarbonylmethoxy trinems was accomplished through Lewis acid catalysed opening of an epoxide intermediate with allyl glycolate, followed by deallylation, activation of the free acid via the 2-pyridyl thiolester and reaction with a series of trimethylsilylamines. An alternative route involving a rhodium-catalysed diazoacetate insertion was also successfully exploited. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01053-3