(4S,5R)-5-azidomethyl-1-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxy)pyrrolidin-2-one | 880548-61-8

• 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: (4S,5R)-5-azidomethyl-1-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxy)pyrrolidin-2-one
• 英文别名: tert-butyl (2R,3S)-2-(azidomethyl)-3-[tert-butyl(diphenyl)silyl]oxy-5-oxopyrrolidine-1-carboxylate
• CAS: 880548-61-8
• 化学式: C₂₆H₃₄N₄O₄Si
• 分子量: 494.666
• InChiKey: IISMUESRNBLEDI-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5R)-5-azidomethyl-1-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxy)pyrrolidin-2-one 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、303.97 kPa 条件下， 反应 48.0h， 以92%的产率得到(4S,5R)-5-(tert-butoxycarbonylamino)-4-(tert-butyldiphenylsilyloxy)piperidin-2-one
  参考文献：
  名称：

  A Stereocontrolled Formal Asymmetric Synthesis of Pseudodistomin C

  摘要：

  An efficient and stereocontrolled formal asymmetric synthesis of pseudodistomin C has been achieved by employing intramolecular transamidation reaction, exo-methylenation, and highly stercoselective hydroboration. The resulting 2-hydroxymethylpiperidine derivative (15) was further converted into the key intermediate (2) for the synthesis of pseudodistomin C.

  DOI：

  10.3987/com-05-10586
• 作为产物：
  描述：

  bicyclic (2R,5R,6R)-6-hydroxy-2-phenyl-3-oxa-1-azabicyclo<3.3.0>octan-8-one 在 palladium on activated charcoal 咪唑 、 4-二甲氨基吡啶 、 sodium azide 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.0h， 生成 (4S,5R)-5-azidomethyl-1-tert-butoxycarbonyl-4-(tert-butyldiphenylsilyloxy)pyrrolidin-2-one
  参考文献：
  名称：

  A Stereocontrolled Formal Asymmetric Synthesis of Pseudodistomin C

  摘要：

  An efficient and stereocontrolled formal asymmetric synthesis of pseudodistomin C has been achieved by employing intramolecular transamidation reaction, exo-methylenation, and highly stercoselective hydroboration. The resulting 2-hydroxymethylpiperidine derivative (15) was further converted into the key intermediate (2) for the synthesis of pseudodistomin C.

  DOI：

  10.3987/com-05-10586

文献信息

• A Stereocontrolled Formal Asymmetric Synthesis of Pseudodistomin C
  作者：Ken-ichi Tanaka、Takuya Maesoba、Hiroyuki Sawanishi

  DOI：10.3987/com-05-10586

  日期：——

  An efficient and stereocontrolled formal asymmetric synthesis of pseudodistomin C has been achieved by employing intramolecular transamidation reaction, exo-methylenation, and highly stercoselective hydroboration. The resulting 2-hydroxymethylpiperidine derivative (15) was further converted into the key intermediate (2) for the synthesis of pseudodistomin C.