2,4-dioxo-3-azaspiro[5.5]undecan-3-yl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoate | 1280225-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,4-dioxo-3-azaspiro[5.5]undecan-3-yl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoate
• CAS: 1280225-72-0
• 化学式: C₃₅H₄₃N₃O₈
• 分子量: 633.742
• InChiKey: DAECVIYJXYTOEV-NDEPHWFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  46.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  140.34
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  L-缬氨酸甲酯 、 2,4-dioxo-3-azaspiro[5.5]undecan-3-yl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoate 在 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 10.08h， 以78%的产率得到Fmoc-L-Orn(Boc)-Val-OMe
  参考文献：
  名称：

  Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids

  摘要：

  A simple two step procedure for the synthesis of a dipeptide from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) activated a-amino acids is described. In presence of DCC, N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione readily esterifies the carboxylic acid group of all the N-protected amino acids to yield crystalline N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy ester. The N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy esters of N-protected amino acids readily condensed with other amino acids and gave a dipeptide. This new method is effective for the DCC coupling of a variety of chiral amino acids without loss of enantiomeric purity. Synthesis of fifteen dipeptides including the hitherto unreported Fmoc-L-Orn(Boc)-Val-OMe. Fmoc-L-Cys(trt)-Gly-OEt and Boc-L-Tyr-Gly-OEt is presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.12.021
• 作为产物：
  描述：

  N-羟基-3,3-环戊烷戊二酰亚胺 、 N-Fmoc-N'-Boc-L-鸟氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以100%的产率得到2,4-dioxo-3-azaspiro[5.5]undecan-3-yl (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((tert-butoxycarbonyl)amino)pentanoate
  参考文献：
  名称：

  Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids

  摘要：

  A simple two step procedure for the synthesis of a dipeptide from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) activated a-amino acids is described. In presence of DCC, N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione readily esterifies the carboxylic acid group of all the N-protected amino acids to yield crystalline N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy ester. The N-hydroxy-3-aza spiro[5,5]undecane-2,4-dione activated carboxy esters of N-protected amino acids readily condensed with other amino acids and gave a dipeptide. This new method is effective for the DCC coupling of a variety of chiral amino acids without loss of enantiomeric purity. Synthesis of fifteen dipeptides including the hitherto unreported Fmoc-L-Orn(Boc)-Val-OMe. Fmoc-L-Cys(trt)-Gly-OEt and Boc-L-Tyr-Gly-OEt is presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.12.021