(1R,3R,4R,5R,6S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]heptane-5,6-diol | 187039-32-3

• 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: (1R,3R,4R,5R,6S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]heptane-5,6-diol
• 英文别名: (1R,3R,4R,5R,6S)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azabicyclo[2.2.1]heptane-5,6-diol
• CAS: 187039-32-3
• 化学式: C₁₈H₂₅NO₄
• 分子量: 319.401
• InChiKey: YJBQXQLGLWNVAJ-KWRZAIAESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  62.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,3R,4R,5R,6S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]heptane-5,6-diol 在 palladium on activated charcoal 水 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 (1R,3R,4R,5R,6S)-3-((S)-1,2-Dihydroxy-ethyl)-2-aza-bicyclo[2.2.1]heptane-5,6-diol; hydrochloride
  参考文献：
  名称：

  Synthesis of Azasugars via Lanthanide-Promoted Aza Diels−Alder Reactions in Aqueous Solution

  摘要：

  Aqueous aza Diels-Alder reactions of chiral aldehydes, prepared from carbohydrates, with benzylamine hydrochloride and cyclopentadiene, were promoted by lanthanide triflates. The exo/endo selectivities and diastereoselectivities of the reactions were elucidated by NMR, CD spectroscopy, and X-ray crystallography. The nitrogen-containing heterocyclic products were further transformed to azasugars, which are potential inhibitors against glycoprocessing enzymes.

  DOI：

  10.1021/jo962074s
• 作为产物：
  描述：

  (1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene 在 吡啶 、 四氧化锇 、 十二/十四烷基二甲基氧化胺 作用下， 以 水 、 异丙醇 为溶剂， 以84%的产率得到(1R,3R,4R,5R,6S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]heptane-5,6-diol
  参考文献：
  名称：

  Synthesis of Azasugars via Lanthanide-Promoted Aza Diels−Alder Reactions in Aqueous Solution

  摘要：

  Aqueous aza Diels-Alder reactions of chiral aldehydes, prepared from carbohydrates, with benzylamine hydrochloride and cyclopentadiene, were promoted by lanthanide triflates. The exo/endo selectivities and diastereoselectivities of the reactions were elucidated by NMR, CD spectroscopy, and X-ray crystallography. The nitrogen-containing heterocyclic products were further transformed to azasugars, which are potential inhibitors against glycoprocessing enzymes.

  DOI：

  10.1021/jo962074s