tert-butyl (2S,3S)-2-[(Z)-2-[(4S)-2-oxo-1,3-oxazolidin-4-yl]ethenyl]-3-(2-trimethylsilylethoxymethoxy)pyrrolidine-1-carboxylate | 142433-36-1

• 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,3S)-2-[(Z)-2-[(4S)-2-oxo-1,3-oxazolidin-4-yl]ethenyl]-3-(2-trimethylsilylethoxymethoxy)pyrrolidine-1-carboxylate
• CAS: 142433-36-1
• 化学式: C₂₀H₃₆N₂O₆Si
• 分子量: 428.601
• InChiKey: IVOBBLTULJJIMU-FUYDUDRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  86.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S)-2-[(Z)-2-[(4S)-2-oxo-1,3-oxazolidin-4-yl]ethenyl]-3-(2-trimethylsilylethoxymethoxy)pyrrolidine-1-carboxylate 在 palladium dihydroxide 四丁基氟化铵 、 氢气 作用下， 以 吡啶 、 六甲基磷酰三胺 、 乙酸乙酯 为溶剂， 反应 27.58h， 生成 (1S,6S,8aS)-1-acetoxy-6-(N-acetylamino)-1,2,3,5,6,7,8,8a-octahydroindolizin
  参考文献：
  名称：

  Enantiospecific Synthesis of (−)-Slaframine and Related Hydroxylated Indolizidines. Utilization of a Nucleophilic Alaninol Synthon Derived from Serine¹

  摘要：

  A general methodology for the synthesis of indolizidine alkaloids delta-coniceine (12), 1-hydroxyindolizidine (20), desacetoxy slaframine (24), slaframine (34), and an analogue (37) has been developed. This convergent approach utilizes the available chirality in proline and serine and is conceptually different from other approaches. A highly stereoselective coupling of the prolinals with a nucleophilic alaninol synthon provides the precursors for the key cyclization. A novel thermolytic annulation of an oxazolidinone is the key step in the formation of the six-membered piperidine ring. Further elaboration provides the target natural products 24, 34, and 37 in good overall yields.

  DOI：

  10.1021/jo9908546
• 作为产物：
  描述：

  tert-butyl (2R,3S)-2-formyl-3-(2-trimethylsilylethoxymethoxy)pyrrolidine-1-carboxylate 、 [4(R)-2-oxo-1,3-oxazolidin-4-ylmethyl]triphenylphosphonium iodide 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以53%的产率得到tert-butyl (2S,3S)-2-[(Z)-2-[(4S)-2-oxo-1,3-oxazolidin-4-yl]ethenyl]-3-(2-trimethylsilylethoxymethoxy)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Enantiospecific Synthesis of (−)-Slaframine and Related Hydroxylated Indolizidines. Utilization of a Nucleophilic Alaninol Synthon Derived from Serine¹

  摘要：

  A general methodology for the synthesis of indolizidine alkaloids delta-coniceine (12), 1-hydroxyindolizidine (20), desacetoxy slaframine (24), slaframine (34), and an analogue (37) has been developed. This convergent approach utilizes the available chirality in proline and serine and is conceptually different from other approaches. A highly stereoselective coupling of the prolinals with a nucleophilic alaninol synthon provides the precursors for the key cyclization. A novel thermolytic annulation of an oxazolidinone is the key step in the formation of the six-membered piperidine ring. Further elaboration provides the target natural products 24, 34, and 37 in good overall yields.

  DOI：

  10.1021/jo9908546