(2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-(4-(tert-butyldimethylsilyloxy)but-1-ynyl)piperidin-1-ol | 1395819-49-4

• 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,3S)-3-(tert-butyldiphenylsilyloxy)-2-(4-(tert-butyldimethylsilyloxy)but-1-ynyl)piperidin-1-ol
• 英文别名: tert-butyl-[(2R,3S)-2-[4-[tert-butyl(dimethyl)silyl]oxybut-1-ynyl]-1-hydroxypiperidin-3-yl]oxy-diphenylsilane
• CAS: 1395819-49-4
• 化学式: C₃₁H₄₇NO₃Si₂
• 分子量: 537.89
• InChiKey: PHFXJVPQIITMDE-WDYNHAJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-(4-(tert-butyldimethylsilyloxy)but-1-ynyl)piperidin-1-ol 在 5%-palladium/activated carbon 、 氢气 作用下， 反应 12.0h， 以90%的产率得到tert-butyl-[(2R,3S)-2-[4-[tert-butyl(dimethyl)silyl]oxybutyl]-1-hydroxypiperidin-3-yl]oxy-diphenylsilane
  参考文献：
  名称：

  A Divergent Approach to 3-Piperidinols: A Concise Syntheses of (+)-Swainsonine and Access to the 1-Substituted Quinolizidine Skeleton

  摘要：

  Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine N-oxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a diversity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1-substituted quinolizidine of utility in target-directed synthesis is reported.

  DOI：

  10.1021/jo3011914
• 作为产物：
  描述：

  (2S)-2-(tert-butyldiphenylsilyloxy)pentane-1,5-diol 在 manganese(IV) oxide 、 正丁基锂 、 盐酸羟胺 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.25h， 生成 (2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-(4-(tert-butyldimethylsilyloxy)but-1-ynyl)piperidin-1-ol
  参考文献：
  名称：

  A Divergent Approach to 3-Piperidinols: A Concise Syntheses of (+)-Swainsonine and Access to the 1-Substituted Quinolizidine Skeleton

  摘要：

  Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine N-oxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a diversity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1-substituted quinolizidine of utility in target-directed synthesis is reported.

  DOI：

  10.1021/jo3011914

文献信息

• A Divergent Approach to 3-Piperidinols: A Concise Syntheses of (+)-Swainsonine and Access to the 1-Substituted Quinolizidine Skeleton
  作者：Glenn Archibald、Chih-Pei Lin、Peter Boyd、David Barker、Vittorio Caprio

  DOI：10.1021/jo3011914

  日期：2012.9.21

  Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine N-oxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a diversity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1-substituted quinolizidine of utility in target-directed synthesis is reported.