tert-butyl (2S,3R,4R)-3-acetoxy-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate | 1225055-48-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (2S,3R,4R)-3-acetoxy-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate
• 英文别名: tert-butyl (2S,3R,4R)-3-acetyloxy-4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidine-1-carboxylate
• CAS: 1225055-48-0
• 化学式: C₁₉H₂₇NO₆
• 分子量: 365.426
• InChiKey: MJTIBNNIAGQOJB-GVDBMIGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3R,4R)-3-acetoxy-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate 在 indium(III) triflate 、 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 8.0h， 以83%的产率得到tert-butyl (2S,3R,4R)-3-acetoxy-4-hydroxy-2-(3-iodo-4-methoxybenzyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Mild Arming and Derivatization of Natural Products via an In(OTf)₃-Catalyzed Arene Iodination

  摘要：

  Iodination of arene-containing natural products employing N-iodosuccinimide catalyzed by In(OTf)(3) at ambient temperature is reported as a versatile and mild method for natural product derivatization amenable to small scale. This process facilitates natural product derivatization of arene moieties for SAR studies, homo- and heterodimerization of natural products, and also conjugation with reporters such as biotin via subsequent metal-mediated coupling reactions.

  DOI：

  10.1021/ol100587j
• 作为产物：
  描述：

  anisomycin 、 二碳酸二叔丁酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以98%的产率得到tert-butyl (2S,3R,4R)-3-acetoxy-4-hydroxy-2-(4-methoxybenzyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Mild Arming and Derivatization of Natural Products via an In(OTf)₃-Catalyzed Arene Iodination

  摘要：

  Iodination of arene-containing natural products employing N-iodosuccinimide catalyzed by In(OTf)(3) at ambient temperature is reported as a versatile and mild method for natural product derivatization amenable to small scale. This process facilitates natural product derivatization of arene moieties for SAR studies, homo- and heterodimerization of natural products, and also conjugation with reporters such as biotin via subsequent metal-mediated coupling reactions.

  DOI：

  10.1021/ol100587j