1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-glutarimido-β-D-glucopyranose | 449762-99-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-glutarimido-β-D-glucopyranose
• 英文别名: 1-[(1R,2S,3S,4R,5R)-2,4-bis[[tert-butyl(dimethyl)silyl]oxy]-6,8-dioxabicyclo[3.2.1]octan-3-yl]piperidine-2,6-dione
• CAS: 449762-99-6
• 化学式: C₂₃H₄₃NO₆Si₂
• 分子量: 485.769
• InChiKey: PEVXSWLROFNDDC-DDVIMMDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  74.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-glutarimido-β-D-glucopyranose 以 乙腈 为溶剂， 反应 4.0h， 以25%的产率得到(1R,2R,3R,10S,11R)-4-aza-2,10-bis-tert-butyldimethylsilyloxy-13,14-dioxa-tricyclo[9.2.1.0^3,10]tetradecane-5,9-dione
  参考文献：
  名称：

  Photochemical Transformation of Levoglucosan Imides to Anhydrosugar-Annelated Azepanediones and Azocanediones

  摘要：

  By reaction of O-protected 3-amino-1,6-anhydro-beta-D-glucopyranose with succinic, glutaric, and tartaric anhydride, respectively, the corresponding 3-substituted succinimido, glutarimido, and tatarimido derivatives were obtained. Irradiation of the succinimido and glutarimido derivatives at 254 nm gave 1,4-diradical intermediates by gamma-hydrogen abstraction (Norrish Type 11 reaction) which subsequently recombined (Yang cyclization) to form azetidinols. These in turn fragmented and led to azepanedione and azocanedione derivatives. In contrast, irradiation of the tartarimido derivative resulted in elimination and led to both isomeric enolethers.

  DOI：

  10.1007/s007060200023
• 作为产物：
  描述：

  1,6-anhydro-3-azido-3-deoxy-β-D-glucopyranose 在 palladium on activated charcoal 氢气 、 乙酸酐 、 N,N-二异丙基乙胺 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 116.0h， 生成 1,6-anhydro-2,4-bis-O-(tert-butyldimethylsilyl)-3-deoxy-3-N-glutarimido-β-D-glucopyranose
  参考文献：
  名称：

  Photochemical Transformation of Levoglucosan Imides to Anhydrosugar-Annelated Azepanediones and Azocanediones

  摘要：

  By reaction of O-protected 3-amino-1,6-anhydro-beta-D-glucopyranose with succinic, glutaric, and tartaric anhydride, respectively, the corresponding 3-substituted succinimido, glutarimido, and tatarimido derivatives were obtained. Irradiation of the succinimido and glutarimido derivatives at 254 nm gave 1,4-diradical intermediates by gamma-hydrogen abstraction (Norrish Type 11 reaction) which subsequently recombined (Yang cyclization) to form azetidinols. These in turn fragmented and led to azepanedione and azocanedione derivatives. In contrast, irradiation of the tartarimido derivative resulted in elimination and led to both isomeric enolethers.

  DOI：

  10.1007/s007060200023

文献信息

• Photochemical Transformation of Levoglucosan Imides to Anhydrosugar-Annelated Azepanediones and Azocanediones
  作者：Christian Sund、Swantje Thiering、Joachim Thiem、Jürgen Kopf、Markus Stark

  DOI：10.1007/s007060200023

  日期：2002.4.1

  By reaction of O-protected 3-amino-1,6-anhydro-beta-D-glucopyranose with succinic, glutaric, and tartaric anhydride, respectively, the corresponding 3-substituted succinimido, glutarimido, and tatarimido derivatives were obtained. Irradiation of the succinimido and glutarimido derivatives at 254 nm gave 1,4-diradical intermediates by gamma-hydrogen abstraction (Norrish Type 11 reaction) which subsequently recombined (Yang cyclization) to form azetidinols. These in turn fragmented and led to azepanedione and azocanedione derivatives. In contrast, irradiation of the tartarimido derivative resulted in elimination and led to both isomeric enolethers.