ethyl 2-((2S,4R,5S)-4-(tert-butoxycarbonylamino)-5-(3,5-dimethoxyphenyl)-1-tosylpyrrolidin-2-yl)acetate | 1429516-72-2

• 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: ethyl 2-((2S,4R,5S)-4-(tert-butoxycarbonylamino)-5-(3,5-dimethoxyphenyl)-1-tosylpyrrolidin-2-yl)acetate
• CAS: 1429516-72-2
• 化学式: C₂₈H₃₈N₂O₈S
• 分子量: 562.684
• InChiKey: JQWGJUKPIOWOBV-KHMOSXFSSA-N

物化性质

• 密度：
  1.27±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  120.47
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-((2S,4R,5S)-4-(tert-butoxycarbonylamino)-5-(3,5-dimethoxyphenyl)-1-tosylpyrrolidin-2-yl)acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以90%的产率得到tert-butyl (2S,3R,5S)-2-(3,5-dimethoxyphenyl)-5-(2-hydroxyethyl)-1-tosylpyrrolidin-3-ylcarbamate
  参考文献：
  名称：

  A Highly Diastereoselective and Enantioselective Synthesis of Polysubstituted Pyrrolidines via an Organocatalytic Dynamic Kinetic Resolution Cascade

  摘要：

  Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50 - 95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.

  DOI：

  10.1021/ol4006129
• 作为产物：
  描述：

  N-(3,5-dimethoxybenzylidene)-4-methylbenzenesulfonamide 在 palladium on activated charcoal 、 C₃₅H₄₇N₃O₂ 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 27.0h， 生成 ethyl 2-((2S,4R,5S)-4-(tert-butoxycarbonylamino)-5-(3,5-dimethoxyphenyl)-1-tosylpyrrolidin-2-yl)acetate
  参考文献：
  名称：

  A Highly Diastereoselective and Enantioselective Synthesis of Polysubstituted Pyrrolidines via an Organocatalytic Dynamic Kinetic Resolution Cascade

  摘要：

  Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50 - 95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.

  DOI：

  10.1021/ol4006129