(3aR,4S,5S,6S,7R,7aR)-7-amino-7a-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4,5,6-triol | 1443540-39-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4S,5S,6S,7R,7aR)-7-amino-7a-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4,5,6-triol
• CAS: 1443540-39-3
• 化学式: C₁₆H₃₃NO₆Si
• 分子量: 363.527
• InChiKey: JCBHSZQDYDGILP-WRBUKDQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.32
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  114.4
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3aR,4S,5S,6S,7R,7aR)-7-amino-7a-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethylhexahydrobenzo[d][1,3]dioxole-4,5,6-triol 在 盐酸 作用下， 以 水 为溶剂， 反应 24.0h， 以80%的产率得到(1R,2R,3R,4S,5S,6S)-2,3,4,5,6-pentahydroxy-2-(hydroxymethyl)cyclohexylammonium chloride
  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：

  ((3aR,7aR)-2,2-dimethyl-3a,7a-dihydrobenzo[d][1,3]dioxol-3a-yl)methanol 在 四氧化锇 、 palladium 10% on activated carbon 、 氢气 、 四丁基高碘酸铵 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 、 叔丁醇 为溶剂， 反应 93.08h， 生成 (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