tert-butyl (2R,3S,4S)-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-trimethylsilyloxymethyl]-3,4-dihydroxy-5-oxopyrrolidine-1-carboxylate | 141293-17-6

• 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: tert-butyl (2R,3S,4S)-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-trimethylsilyloxymethyl]-3,4-dihydroxy-5-oxopyrrolidine-1-carboxylate
• CAS: 141293-17-6
• 化学式: C₁₈H₃₃NO₈Si
• 分子量: 419.547
• InChiKey: FSMLFVOLTFOGQA-PEBLQZBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.23
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (2R,3S,4S)-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-trimethylsilyloxymethyl]-3,4-dihydroxy-5-oxopyrrolidine-1-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到(3S,4S,5S)-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：

  N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole 在 吡啶 、 二环己烷并-18-冠醚-6 、 potassium permanganate 、 四氯化锡 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 tert-butyl (2R,3S,4S)-2-[(S)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-trimethylsilyloxymethyl]-3,4-dihydroxy-5-oxopyrrolidine-1-carboxylate
  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

• Homochiral α,β-unsaturated γ-lactams: Versatile templates
  作者：Gloria Rassu、Giovanni Casiraghi、Pietro Spanu、Luigi Pinna、Giovanna Gasparri Fava、Marisa Belicchi Ferrari、Giorgio Pelosi

  DOI：10.1016/s0957-4166(00)86037-1

  日期：1992.8

  The enantiomerically pure crystalline alpha,beta-unsaturated gamma-lactams 4 and 5 have been synthesized by utilizing 2,3-O-isopropylidene-D-glyceraldehyde (3) as chiral source and novel N-tert-butoxycarbonyl-2-(tert-butyldimethylsiloxy)pyrrole (TBSOP) as four carbon homologative reagent. Unsaturated lactam 4 has been selectively elaborated into hydroxylated pyrrolidiones 7,8, and 11 by stereocontrolled procedures involving conjugate addition of organocuprates, cis-dihydroxylation, and alpha-alkylation via hydrogenation and enolate formation. The absolute stereochemistries of 4 and 5 have been secured by single crystal X-ray analyses.
• N-(tert-Butoxycarbonyl)-2-(tert-butyldimethylsiloxy)pyrrole: a promising compound for synthesis of chiral nonracemic hydroxylated pyrrolidine derivatives
  作者：Giovanni Casiraghi、Gloria Rassu、Pietro Spanu、Luigi Pinna

  DOI：10.1021/jo00040a006

  日期：1992.7

  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.