(-)-7-tert-butoxycarbonyl-2-{[(tert-butyl)dimethylsilyl]oxy}-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-ene | 726192-21-8

• 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: (-)-7-tert-butoxycarbonyl-2-{[(tert-butyl)dimethylsilyl]oxy}-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-ene
• 英文别名: tert-butyl (1R,2R,6S,7R)-8-[tert-butyl(dimethyl)silyl]oxy-4,4-dimethyl-3,5-dioxa-10-azatricyclo[5.2.1.02,6]dec-8-ene-10-carboxylate
• CAS: 726192-21-8
• 化学式: C₂₀H₃₅NO₅Si
• 分子量: 397.587
• InChiKey: UMVRRVQOSLBAFC-BVUBDWEXSA-N

物化性质

• 沸点：
  419.1±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.41
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-7-tert-butoxycarbonyl-2-{[(tert-butyl)dimethylsilyl]oxy}-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-ene 在 dimethyl sulfide borane 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.42h， 生成 (3aR,4R,6S,6aS)-tert-butyl 4,6-bis(hydroxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate
  参考文献：
  名称：

  Synthesis of d- and l-2,3-trans-3,4-cis-4,5-trans-3,4-Dihydroxy-5-hydroxymethylproline and Tripeptides Containing Them

  摘要：

  Enantiomerically pure (-)-(1R,4R,5R,6S)- and (+)-(1S,4S,5S,6R)-7-(tert-butoxycarbonyl)-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-one ((-)-3 and (+)-3) have been obtained from the Diels-Alder adduct of N-(tert-butoxycarbonyl)pyrrole and 2-bromo-1-(p-toluenesulfonyl)acetylene, including the Alexakis optical resolution of ketone ()-3 via formation of cyclic aminals with (1R,2R)diphenylethylenediamine. Compounds (-)-3 and (+)-3 were converted into D- and L-2,3-trans-3,4-cis-4,5-trans-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-isopropylidenedioxyprolines (-)-4 and (+)4, respectively. Applying the Boc and Fmoc strategies of peptide synthesis, these compounds were used to construct two tripeptides containing the D- or L-2,3-trans-3,4-cis-4,5-trans-3,4-dihydroxy-5-hydroxymethylproline.

  DOI：

  10.1021/jo049637h
• 作为产物：
  描述：

  7-tert-butoxycarbonyl-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]heptan-2-endo-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (-)-7-tert-butoxycarbonyl-2-{[(tert-butyl)dimethylsilyl]oxy}-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-ene
  参考文献：
  名称：

  Synthesis of d- and l-2,3-trans-3,4-cis-4,5-trans-3,4-Dihydroxy-5-hydroxymethylproline and Tripeptides Containing Them

  摘要：

  Enantiomerically pure (-)-(1R,4R,5R,6S)- and (+)-(1S,4S,5S,6R)-7-(tert-butoxycarbonyl)-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-one ((-)-3 and (+)-3) have been obtained from the Diels-Alder adduct of N-(tert-butoxycarbonyl)pyrrole and 2-bromo-1-(p-toluenesulfonyl)acetylene, including the Alexakis optical resolution of ketone ()-3 via formation of cyclic aminals with (1R,2R)diphenylethylenediamine. Compounds (-)-3 and (+)-3 were converted into D- and L-2,3-trans-3,4-cis-4,5-trans-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-isopropylidenedioxyprolines (-)-4 and (+)4, respectively. Applying the Boc and Fmoc strategies of peptide synthesis, these compounds were used to construct two tripeptides containing the D- or L-2,3-trans-3,4-cis-4,5-trans-3,4-dihydroxy-5-hydroxymethylproline.

  DOI：

  10.1021/jo049637h

文献信息

• Synthesis of <scp>d</scp>- and <scp>l</scp>-2,3-<i>trans</i>-3,4-<i>cis</i>-4,5-<i>trans</i>-3,4-Dihydroxy-5-hydroxymethylproline and Tripeptides Containing Them
  作者：Antonio J. Moreno-Vargas、Inmaculada Robina、Elena Petricci、Pierre Vogel

  DOI：10.1021/jo049637h

  日期：2004.6.1

  Enantiomerically pure (-)-(1R,4R,5R,6S)- and (+)-(1S,4S,5S,6R)-7-(tert-butoxycarbonyl)-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-one ((-)-3 and (+)-3) have been obtained from the Diels-Alder adduct of N-(tert-butoxycarbonyl)pyrrole and 2-bromo-1-(p-toluenesulfonyl)acetylene, including the Alexakis optical resolution of ketone ()-3 via formation of cyclic aminals with (1R,2R)diphenylethylenediamine. Compounds (-)-3 and (+)-3 were converted into D- and L-2,3-trans-3,4-cis-4,5-trans-N-(tert-butoxycarbonyl)-5-hydroxymethyl-3,4-isopropylidenedioxyprolines (-)-4 and (+)4, respectively. Applying the Boc and Fmoc strategies of peptide synthesis, these compounds were used to construct two tripeptides containing the D- or L-2,3-trans-3,4-cis-4,5-trans-3,4-dihydroxy-5-hydroxymethylproline.