(1R,5R,6S,7S)-2-Benzyl-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-oxa-2-aza-bicyclo[3.2.0]heptane | 160836-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 英文名称: (1R,5R,6S,7S)-2-Benzyl-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-oxa-2-aza-bicyclo[3.2.0]heptane
• 英文别名: [(1R,5R,6S,7S)-2-benzyl-6-[tert-butyl(dimethyl)silyl]oxy-3-oxa-2-azabicyclo[3.2.0]heptan-7-yl]oxy-tert-butyl-dimethylsilane
• CAS: 160836-06-6
• 化学式: C₂₄H₄₃NO₃Si₂
• 分子量: 449.781
• InChiKey: BJDQWBIFWXLGFI-LRSLUSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  30.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,5R,6S,7S)-2-Benzyl-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-oxa-2-aza-bicyclo[3.2.0]heptane 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 Acetic acid (1R,2R,3S,4S)-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-cyclobutylmethyl ester
  参考文献：
  名称：

  Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines

  摘要：

  Intramolecular cycloaddition reactions of C-5-chain acyclic alkenyl nitrones such as N-[(2S,3S)-2,3-bis-(tert-butyldimethylsiloxy)-4-pentenylidene]benzylamine N-oxide and its C(5)-substituted derivatives lead to fused isoxazolidines (bicyclo[3.2.0] framework) with very high diastereomeric excess. These isoxazolidines can readily be converted to optically active tetrasubstituted cyclobutylamines.

  DOI：

  10.1021/jo00095a008
• 作为产物：
  描述：

  (2R,3S)-2,3-bis(tert-butyldimethylsilyloxy)-4-pentenal 以 二氯甲烷 、 苯 为溶剂， 反应 13.0h， 生成 (1R,5R,6S,7S)-2-Benzyl-6,7-bis-(tert-butyl-dimethyl-silanyloxy)-3-oxa-2-aza-bicyclo[3.2.0]heptane
  参考文献：
  名称：

  Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines

  摘要：

  Intramolecular cycloaddition reactions of C-5-chain acyclic alkenyl nitrones such as N-[(2S,3S)-2,3-bis-(tert-butyldimethylsiloxy)-4-pentenylidene]benzylamine N-oxide and its C(5)-substituted derivatives lead to fused isoxazolidines (bicyclo[3.2.0] framework) with very high diastereomeric excess. These isoxazolidines can readily be converted to optically active tetrasubstituted cyclobutylamines.

  DOI：

  10.1021/jo00095a008

文献信息

• Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines
  作者：Seiki Saito、Teruhiko Ishikawa、Toshio Moriwake

  DOI：10.1021/jo00095a008

  日期：1994.8

  Intramolecular cycloaddition reactions of C-5-chain acyclic alkenyl nitrones such as N-[(2S,3S)-2,3-bis-(tert-butyldimethylsiloxy)-4-pentenylidene]benzylamine N-oxide and its C(5)-substituted derivatives lead to fused isoxazolidines (bicyclo[3.2.0] framework) with very high diastereomeric excess. These isoxazolidines can readily be converted to optically active tetrasubstituted cyclobutylamines.