Fmoc-L-Orn(Boc)-Val-OMe | 1280225-68-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Fmoc-L-Orn(Boc)-Val-OMe
• 英文别名: Fmoc-Orn(Boc)-Val-OMe；methyl (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]-3-methylbutanoate
• CAS: 1280225-68-4
• 化学式: C₃₁H₄₁N₃O₇
• 分子量: 567.682
• InChiKey: BIGQZEXZLDVTQC-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  41
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-Fmoc-N'-Boc-L-鸟氨酸 在 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.08h， 生成 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

文献信息

• Synthesis of dipeptides from N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione activated α-amino acids
  作者：Shaik Nowshuddin、A. Ram Reddy

  DOI：10.1016/j.tetasy.2010.12.021

  日期：2011.1

  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.