(2R,3R)-tert-butyl 3-[(benzyloxycarbonyl)amino]-2-[(tertbutoxycarbonyl)amino]butanoate | 338972-22-8

• 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: (2R,3R)-tert-butyl 3-[(benzyloxycarbonyl)amino]-2-[(tertbutoxycarbonyl)amino]butanoate
• 英文别名: tert-butyl (2R,3R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(phenylmethoxycarbonylamino)butanoate
• CAS: 338972-22-8
• 化学式: C₂₁H₃₂N₂O₆
• 分子量: 408.495
• InChiKey: MGRYRHPFUQBXKU-GDBMZVCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-tert-butyl 3-[(benzyloxycarbonyl)amino]-2-[(tertbutoxycarbonyl)amino]butanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (2R,3R)-3-Amino-2-tert-butoxycarbonylamino-butyric acid tert-butyl ester
  参考文献：
  名称：

  Total Synthesis of Quinaldopeptin and Its Analogues

  摘要：

  The first total synthesis of quinaldopeptin (1) was accomplished. Our approach to the synthesis of 1 includes the solid-phase peptide synthesis of the linear decapeptide 4 followed by macrocyclization and introduction of the quinoline chromophores 2 at a late stage of the synthesis. As for the preparation of 4, a fragment coupling approach was applied considering the C2 symmetrical structure of 1. Chromophore analogues 22 and 23 and desmethyl analogue 27 were also prepared in a manner similar to the synthesis of 1. Synthetic 1 exhibits a strong cytotoxicity with the IC50 value of 3.2 nM. On the other hand, the activity of 23 and 27 was largely reduced.

  DOI：

  10.1021/jo402267r
• 作为产物：
  描述：

  tert-butyl (2R,3R)-2-azido-3-(phenylmethoxycarbonylamino)butanoate 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 26.0h， 生成 (2R,3R)-tert-butyl 3-[(benzyloxycarbonyl)amino]-2-[(tertbutoxycarbonyl)amino]butanoate
  参考文献：
  名称：

  Total Synthesis of Quinaldopeptin and Its Analogues

  摘要：

  The first total synthesis of quinaldopeptin (1) was accomplished. Our approach to the synthesis of 1 includes the solid-phase peptide synthesis of the linear decapeptide 4 followed by macrocyclization and introduction of the quinoline chromophores 2 at a late stage of the synthesis. As for the preparation of 4, a fragment coupling approach was applied considering the C2 symmetrical structure of 1. Chromophore analogues 22 and 23 and desmethyl analogue 27 were also prepared in a manner similar to the synthesis of 1. Synthetic 1 exhibits a strong cytotoxicity with the IC50 value of 3.2 nM. On the other hand, the activity of 23 and 27 was largely reduced.

  DOI：

  10.1021/jo402267r

文献信息

• The synthesis of β-peptides containing guanidino groups
  作者：Ke Wen、Hyunsoo Han、Timothy Z Hoffman、Kim D Janda、Leslie E Orgel

  DOI：10.1016/s0960-894x(01)00027-0

  日期：2001.3

  The synthesis of the beta -peptide 1 by the postsynthetic modification of the corresponding amino-containing peptide 3 is described. The potential of 1 to act as a template for the ligation of complementary negatively-charged peptides is discussed. (C) 2001 Published by Elsevier Science Ltd.
• Total Synthesis of Quinaldopeptin and Its Analogues
  作者：Satoshi Ichikawa、Takuya Okamura、Akira Matsuda

  DOI：10.1021/jo402267r

  日期：2013.12.20

  The first total synthesis of quinaldopeptin (1) was accomplished. Our approach to the synthesis of 1 includes the solid-phase peptide synthesis of the linear decapeptide 4 followed by macrocyclization and introduction of the quinoline chromophores 2 at a late stage of the synthesis. As for the preparation of 4, a fragment coupling approach was applied considering the C2 symmetrical structure of 1. Chromophore analogues 22 and 23 and desmethyl analogue 27 were also prepared in a manner similar to the synthesis of 1. Synthetic 1 exhibits a strong cytotoxicity with the IC50 value of 3.2 nM. On the other hand, the activity of 23 and 27 was largely reduced.