(1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene | 187039-25-4

• 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: (1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene
• 英文别名: (1R,3R,4S)-2-benzyl-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-azabicyclo[2.2.1]hept-5-ene
• CAS: 187039-25-4
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: FCEHMJSMVFILPY-YYIAUSFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  benzylamine hydrochloride 、 环戊二烯 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 neodymium(III) trifluoromethanesufonate 作用下， 以 水 为溶剂， 反应 48.0h， 生成 (1R,3R,4S)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene 、 (1S,3R,4R)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene 、 (1S,3S,4R)-2-Benzyl-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-aza-bicyclo[2.2.1]hept-5-ene
  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

文献信息

• Synthesis of Azasugars via Lanthanide-Promoted Aza Diels−Alder Reactions in Aqueous Solution
  作者：Libing Yu、Jun Li、Johnny Ramirez、Depu Chen、Peng George Wang

  DOI：10.1021/jo962074s

  日期：1997.2.1

  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.