(3aR,4S,5S,6S,7R,7aR)-benzyl 7a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate | 1443540-34-8

• 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: (3aR,4S,5S,6S,7R,7aR)-benzyl 7a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate
• CAS: 1443540-34-8
• 化学式: C₂₄H₃₇NO₈Si
• 分子量: 495.645
• InChiKey: KTFJPBARLJPFNL-KIQLMJNDSA-N

物化性质

• 沸点：
  578.7±50.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  34.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  106.92
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (3aR,4S,5S,6S,7R,7aR)-benzyl 7a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以45%的产率得到(3aR,4S,5S,6S,7R,7aR)-7-amino-7a-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4,5,6-triol
  参考文献：
  名称：

  New aminocyclitols with quaternary stereocentres via acylnitroso cycloaddition with an ipso,ortho arene dihydrodiol

  摘要：

  Microbial ipso,ortho-dihydroxylation of benzoic acid by the B9 mutant strain of Ralstonia eutropha permits rapid construction of aminocyclitols containing a quaternary stereocentre. Installation of the amine functionality is achieved by use of an acylnitroso dienophile for a hetero-Diels-Alder reaction. Both aminotetrols and aminohexols are accessible as single enantiomers by this route. Both NOESY spectroscopic and X-ray crystallographic analyses were required to distinguish cycloadduct isomers. Notably, subsequent to the biooxidation step, all new stereocentres are installed under substrate control. Thus, all stereochemical information is ultimately of enzymatic origin. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.033
• 作为产物：
  描述：

  tert-butyl(((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methoxy)dimethylsilane 在 四氧化锇 、 四丁基高碘酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 68.0h， 生成 (3aR,4S,5S,6S,7R,7aR)-benzyl 7a-(((tert-butyldimethylsilyl)oxy)methyl)-5,6-dihydroxy-2,2-dimethylhexahydro-4,7-(epoxyimino)benzo[d][1,3]dioxole-8-carboxylate 、 (3aS,4S,4aR,7aR,8R,8aS)-7a-(((tert-butyldimethylsilyl)oxy)methyl)-6,6-dimethylhexahydro-4,8-(epoxyimino)benzo[1,2-d:4,5-d']bis([1,3]dioxole)-2-one
  参考文献：
  名称：

  New aminocyclitols with quaternary stereocentres via acylnitroso cycloaddition with an ipso,ortho arene dihydrodiol

  摘要：

  Microbial ipso,ortho-dihydroxylation of benzoic acid by the B9 mutant strain of Ralstonia eutropha permits rapid construction of aminocyclitols containing a quaternary stereocentre. Installation of the amine functionality is achieved by use of an acylnitroso dienophile for a hetero-Diels-Alder reaction. Both aminotetrols and aminohexols are accessible as single enantiomers by this route. Both NOESY spectroscopic and X-ray crystallographic analyses were required to distinguish cycloadduct isomers. Notably, subsequent to the biooxidation step, all new stereocentres are installed under substrate control. Thus, all stereochemical information is ultimately of enzymatic origin. (C) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.033