(2R,5R,6S)-6-(tert-butyldiphenylsilyloxy)-3-oxa-2-phenyl-1-azabicyclo[3.3.0]octane-8-one | 880548-58-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,5R,6S)-6-(tert-butyldiphenylsilyloxy)-3-oxa-2-phenyl-1-azabicyclo[3.3.0]octane-8-one
• 英文别名: (3R,7S,7aR)-7-[tert-butyl(diphenyl)silyl]oxy-3-phenyl-3,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-5-one
• CAS: 880548-58-3
• 化学式: C₂₈H₃₁NO₃Si
• 分子量: 457.645
• InChiKey: LRHHAPFWQKOYLF-CMTIAEDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5R,6S)-6-(tert-butyldiphenylsilyloxy)-3-oxa-2-phenyl-1-azabicyclo[3.3.0]octane-8-one 在 palladium on activated charcoal 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 36.0h， 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
• 作为产物：
  描述：

  (2R,5R,6R,7R)-6,7-epoxy-2-phenyl-3-oxa-1-aza-bicyclo<3.3.0>octane-8-one 在 咪唑 、 sodium tetrahydroborate 、 二苯基二硒醚 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 (2R,5R,6S)-6-(tert-butyldiphenylsilyloxy)-3-oxa-2-phenyl-1-azabicyclo[3.3.0]octane-8-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.