(5S)-1-(tert-butoxycarbonyl)-5-{(S)-trimethylsilanyloxy[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1H-pyrrol-2(5H)-one | 141393-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: (5S)-1-(tert-butoxycarbonyl)-5-{(S)-trimethylsilanyloxy[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1H-pyrrol-2(5H)-one
• 英文别名: tert-butyl (2S)-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-trimethylsilyloxymethyl]-5-oxo-2H-pyrrole-1-carboxylate
• CAS: 141393-84-2
• 化学式: C₁₈H₃₁NO₆Si
• 分子量: 385.533
• InChiKey: DTRVGCCVWNIZFY-GUTXKFCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (5S)-1-(tert-butoxycarbonyl)-5-{(S)-trimethylsilanyloxy[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1H-pyrrol-2(5H)-one 在 二环己烷并-18-冠醚-6 、 potassium permanganate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (3R,4R,5R)-3,4-Dihydroxy-5-((1S,2R)-1,2,3-trihydroxy-propyl)-pyrrolidin-2-one
  参考文献：
  名称：

  N-(tert-Butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole: a promising compound for synthesis of chiral nonracemic hydroxylated pyrrolidine derivatives

  摘要：

  N-t-Boc-2-(tert-butyldimethylsiloxy)pyrrole has been synthesized from pyrrole and used to prepare enantiomerically pure pyrrolinones 5, 6, 15, and 16 and polyhydroxylated pyrrolidinones of type 11 and 12.

  DOI：

  10.1021/jo00040a006
• 作为产物：
  描述：

  (1'S,2R,4''R)-2-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (5S)-1-(tert-butoxycarbonyl)-5-{(S)-trimethylsilanyloxy[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  N-(tert-Butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole: a promising compound for synthesis of chiral nonracemic hydroxylated pyrrolidine derivatives

  摘要：

  N-t-Boc-2-(tert-butyldimethylsiloxy)pyrrole has been synthesized from pyrrole and used to prepare enantiomerically pure pyrrolinones 5, 6, 15, and 16 and polyhydroxylated pyrrolidinones of type 11 and 12.

  DOI：

  10.1021/jo00040a006

文献信息

• Vicarious Silylative Mukaiyama Aldol Reaction: A Vinylogous Extension
  作者：Claudio Curti、Andrea Sartori、Lucia Battistini、Gloria Rassu、Paola Burreddu、Franca Zanardi、Giovanni Casiraghi

  DOI：10.1021/jo800741c

  日期：2008.7.1

  A vinylogous, silylative, and direct variant of the venerable Mukaiyama aldol reaction has been developed. Exploiting N-Boc-pyrrol-2(5H)-one as the conjugate donor, several aldehyde and ketone acceptors were scrutinized under the guidance of suitable dual Lewis acid-Lewis base activators to provide a varied repertoire of functionality-rich alpha,beta-unsaturated-gamma-amino-delta-silyloxy carbonyl structures, in useful yields and often with an exquisite level of diastereoselection.