(2S,5S)-N-(tert-butoxycarbonyl)-5[(tert-butyldiphenylsilyl)oxymethyl]-2-methoxypyrrolidine | 782496-03-1

• 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: (2S,5S)-N-(tert-butoxycarbonyl)-5[(tert-butyldiphenylsilyl)oxymethyl]-2-methoxypyrrolidine
• 英文别名: (2S,5S)-N-tert-butoxycarbonyl-2-(tert-butyldiphenylsilyloxy)-methyl-5-methoxy-pyrrolidine；tert-butyl (2S,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-methoxypyrrolidine-1-carboxylate
• CAS: 782496-03-1
• 化学式: C₂₇H₃₉NO₄Si
• 分子量: 469.696
• InChiKey: PKWYTGITAUXGAK-URXFXBBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,5S)-N-(tert-butoxycarbonyl)-5[(tert-butyldiphenylsilyl)oxymethyl]-2-methoxypyrrolidine 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 叔丁基二甲硅基三氟甲磺酸酯 、 氢气 、 sodium methylate 、 sodium acetate 、 苯硫酚 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 (3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one
  参考文献：
  名称：

  Lewis Acid Assisted Vinylogous Mannich and Mukaiyama Aldol Reactions: A Route to Densely Hydroxylated Indolizidine Alkaloid Analogues

  摘要：

  The hydroxymethyl-substituted indolizidines 6 and 7, representative members of a ring-B-expanded alexine- australine subclass, are readily accessible by starting with furan-based silyloxydiene 12 and hydroxymethyl hemiaminal 11, through a synthesis sequence involving a scantily exploited vinylogous version of the Mannich reaction. The key iminium electrophilic acceptor 11 is, in turn, available through a vinylogous intermolecular Mukaiyama aldolization process between pyrrole-based silyloxydiene 8 and (S)-glyceraldehyde 9.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1395::aid-ejoc1395>3.0.co;2-t
• 作为产物：
  描述：

  (S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate 在 三氟化硼乙醚 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.5h， 生成 (2S,5S)-N-(tert-butoxycarbonyl)-5[(tert-butyldiphenylsilyl)oxymethyl]-2-methoxypyrrolidine
  参考文献：
  名称：

  Lewis Acid Assisted Vinylogous Mannich and Mukaiyama Aldol Reactions: A Route to Densely Hydroxylated Indolizidine Alkaloid Analogues

  摘要：

  The hydroxymethyl-substituted indolizidines 6 and 7, representative members of a ring-B-expanded alexine- australine subclass, are readily accessible by starting with furan-based silyloxydiene 12 and hydroxymethyl hemiaminal 11, through a synthesis sequence involving a scantily exploited vinylogous version of the Mannich reaction. The key iminium electrophilic acceptor 11 is, in turn, available through a vinylogous intermolecular Mukaiyama aldolization process between pyrrole-based silyloxydiene 8 and (S)-glyceraldehyde 9.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1395::aid-ejoc1395>3.0.co;2-t

文献信息

• Stereoselective Synthesis oftrans-threo-trans-Oligopyrrolidines: Potential Agents for RNA Cleavage
  作者：Hans-Dieter Arndt、Rüdiger Welz、Sabine Müller、Burkhart Ziemer、Ulrich Koert

  DOI：10.1002/chem.200400181

  日期：2004.8.20

  The 2,5-trans-substituted oligopyrrolidines constitute a promising class of novel RNA-binding agents as well as potential building blocks for artificial anion channels. A convergent synthesis of terpyrrolidine 1 and pyrrolidino-THF-pyrrolidine 2 is reported, relying upon convergent coupling of 2,5-trans-pyrrolidinecarboxaldehydes through bridging alkyne units under Felkin-Anh control and subsequent

  2,5-反式取代的低聚吡咯烷酮构成一类有前途的新型RNA结合剂以及潜在的人造阴离子通道的组成部分。据报道，通过在Felkin-Anh控制下通过桥接炔基单元并随后封闭中心环，2,5-反式-吡咯烷甲醛的收敛偶联，可以实现对吡咯烷1和吡咯烷基-THF-吡咯烷2的收敛合成。完全脱保护后，以优异的产率和纯度分离出游离的多胺产物。特吡咯烷和吡咯烷基-THF-吡咯烷的晶体结构分析证明了它们的螺旋特权构象。然后筛选化合物的RNA切割活性。与仅有的弱活性简单多胺不同，