(2S,3S)-1-(4-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)benzyl) 4-benzyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tertbutyldimethylsilyloxy)succinate | 1357485-73-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,3S)-1-(4-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)benzyl) 4-benzyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tertbutyldimethylsilyloxy)succinate
• CAS: 1357485-73-4
• 化学式: C₅₂H₆₂N₂O₉Si
• 分子量: 887.158
• InChiKey: DZWLIHBGKCDAGS-MVRBIKRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.44
• 重原子数：
  64.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  146.33
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-1-(4-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)benzyl) 4-benzyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tertbutyldimethylsilyloxy)succinate 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.83h， 以75%的产率得到(2S,3S)-4-(4-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)benzyloxy)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-(tert-butyldimethylsilyloxy)-4-oxobutanoic acid
  参考文献：
  名称：

  A practical synthesis of N α -Fmoc protected l-threo-β-hydroxyaspartic acid derivatives for coupling via α- or β-carboxylic group

  摘要：

  A simple and practical general synthetic protocol towards orthogonally protected tHyAsp derivatives fully compatible with Fmoc solid-phase peptide synthetic methodology is reported. Our approach includes enantioresolution of commercially available d,l-tHyAsp racemic mixture by co-crystallization with l-Lys, followed by ion exchange chromatography yielding enantiomerically pure l-tHyAsp and d-tHyAsp, and their selective orthogonal protection. In this way N (alpha) -Fmoc protected tHyAsp derivatives were prepared ready for couplings via either alpha- or beta-carboxylic group onto the resins or the growing peptide chain. In addition, coupling of tHyAsp via beta-carboxylic group onto amino resins allows preparation of peptides containing tHyAsn sequences, further increasing the synthetic utility of prepared tHyAsp derivatives.

  DOI：

  10.1007/s00726-010-0806-x
• 作为产物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 4-二甲氨基吡啶 、 碳酸氢钠 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 (2S,3S)-1-(4-(1-(4,4-dimethyl-2,6-dioxocyclohexylidene)-3-methylbutylamino)benzyl) 4-benzyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(tertbutyldimethylsilyloxy)succinate
  参考文献：
  名称：

  A practical synthesis of N α -Fmoc protected l-threo-β-hydroxyaspartic acid derivatives for coupling via α- or β-carboxylic group

  摘要：

  A simple and practical general synthetic protocol towards orthogonally protected tHyAsp derivatives fully compatible with Fmoc solid-phase peptide synthetic methodology is reported. Our approach includes enantioresolution of commercially available d,l-tHyAsp racemic mixture by co-crystallization with l-Lys, followed by ion exchange chromatography yielding enantiomerically pure l-tHyAsp and d-tHyAsp, and their selective orthogonal protection. In this way N (alpha) -Fmoc protected tHyAsp derivatives were prepared ready for couplings via either alpha- or beta-carboxylic group onto the resins or the growing peptide chain. In addition, coupling of tHyAsp via beta-carboxylic group onto amino resins allows preparation of peptides containing tHyAsn sequences, further increasing the synthetic utility of prepared tHyAsp derivatives.

  DOI：

  10.1007/s00726-010-0806-x