methyl (2S)-2-tert-butoxycarbonylamino-5-oxo-8-(diphenylmethyleneimino)nonanoate | 871691-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (2S)-2-tert-butoxycarbonylamino-5-oxo-8-(diphenylmethyleneimino)nonanoate
• 英文别名: 9-(tert-butyl) 1-methyl (2S)-2-((tert-butoxycarbonyl)amino)-8-((diphenylmethylene)amino)-5-oxononanedioate；9-O-tert-butyl 1-O-methyl (2S)-8-(benzhydrylideneamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxononanedioate
• CAS: 871691-86-0
• 化学式: C₃₂H₄₂N₂O₇
• 分子量: 566.695
• InChiKey: JEVMUXITUXOUCT-PMCHYTPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-tert-butoxycarbonylamino-5-oxo-8-(diphenylmethyleneimino)nonanoate 在 palladium on activated charcoal 三乙基硅烷 、 氢气 、 sodium carbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 (3S,6S,9S)-2-oxo-3-(N-(9-fluorenylmethoxycarbonyl)amino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid
  参考文献：
  名称：

  An Efficient Synthesis of the Constrained Peptidomimetic 2-Oxo-3-(N-9-fluorenyloxy-carbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic Acid from Pyroglutamic Acid

  摘要：

  Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo- [4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.

  DOI：

  10.1021/jo0515935
• 作为产物：
  描述：

  Boc-L-焦谷氨酸甲酯 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 methyl (2S)-2-tert-butoxycarbonylamino-5-oxo-8-(diphenylmethyleneimino)nonanoate
  参考文献：
  名称：

  An Efficient Synthesis of the Constrained Peptidomimetic 2-Oxo-3-(N-9-fluorenyloxy-carbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic Acid from Pyroglutamic Acid

  摘要：

  Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo- [4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.

  DOI：

  10.1021/jo0515935

文献信息

• An Efficient Synthesis of the Constrained Peptidomimetic 2-Oxo-3-(<i>N</i>-9-fluorenyloxy-carbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic Acid from Pyroglutamic Acid
  作者：Pijus Kumar Mandal、Kumar K. Kaluarachchi、Douglas Ogrin、Simon G. Bott、John S. McMurray

  DOI：10.1021/jo0515935

  日期：2005.11.1

  Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo- [4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.