(1S,2S,3R,4R,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline] | 727417-92-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2S,3R,4R,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline]
• 英文别名: tert-butyl (1R,2R,4'R,5'R,6S,7S)-4,4-dimethyl-4',5'-diphenylspiro[3,5-dioxa-10-azatricyclo[5.2.1.02,6]decane-8,2'-imidazolidine]-10-carboxylate
• CAS: 727417-92-7
• 化学式: C₂₈H₃₅N₃O₄
• 分子量: 477.604
• InChiKey: ZRUUCJLYIAXFCN-TZNXUKFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  72.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline] 在 dimethyl sulfide borane 、 磷酸 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.92h， 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：

  (1R,2R)-1,2-二苯基乙二胺 、 (+/-)-7-tert-butoxycarbonyl-5,6-exo-isopropylidenedioxy-7-azabicyclo[2.2.1]hept-2-one 在 4 A molecular sieve 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以44%的产率得到(1R,2R,3S,4S,4'R,5'R)-4',5'-diphenylspiro[2,3-exo-isopropylidenedioxy-7-tert-butoxycarbonyl-7-azabicyclo[2.2.1]hept-2,2'-imidazoline]
  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.