N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane | 437718-36-0

• 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: N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane
• 英文别名: tert-butyl N-[(2S)-4-amino-1-[5-[(2-nitrophenyl)sulfonylamino]pentylamino]-1,4-dioxobutan-2-yl]carbamate
• CAS: 437718-36-0
• 化学式: C₂₀H₃₁N₅O₈S
• 分子量: 501.561
• InChiKey: NLIVNHGRQXRXIM-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  211
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane 在 caesium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2-巯基乙醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 benzyl N-[3-[5-[[(2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoyl]amino]pentylamino]-3-oxopropyl]-N-[4-[(2-nitrophenyl)sulfonyl-[3-(phenylmethoxycarbonylamino)propyl]amino]butyl]carbamate
  参考文献：
  名称：

  An efficient and versatile synthesis of all structural types of acylpolyamine spider toxins

  摘要：

  An efficient and versatile synthesis of acylpolyamine spider toxins of all structural types classified by extensive MS analysis has been achieved. By using 2-nitrobenzenesulfonamide as an effective activating and/or protecting group (the Nosyl strategy), the naturally occurring toxins 1-8 corresponding to Types A-F were concisely synthesized in high overall yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.051
• 作为产物：
  描述：

  丁氧羰基-L-天冬酰胺对硝苯基酯 、 N-(5-氨戊基)-2-硝基苯磺酰胺盐酸盐 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以97%的产率得到N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-N'-(2-nitrobenzenesulfonyl)-1,5-diaminopentane
  参考文献：
  名称：

  An efficient and versatile synthesis of acylpolyamine spider toxins

  摘要：

  An efficient and versatile synthesis of acylpolyamine spider toxins was developed based on the structural classification of the Nephila and Nephilengys spider toxins using the 2-nitrobenzenesulfonamide protecting group. The naturally occurring toxins 1-5 representing each structural type have been efficiently synthesized by this method in a high overall yield with few steps. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00733-8

文献信息

• An efficient and versatile synthesis of acylpolyamine spider toxins
  作者：Ken-ichi Nihei、Massuo J Kato、Tetsuo Yamane、Mario S Palma、Katsuhiro Konno

  DOI：10.1016/s0960-894x(01)00733-8

  日期：2002.2

  An efficient and versatile synthesis of acylpolyamine spider toxins was developed based on the structural classification of the Nephila and Nephilengys spider toxins using the 2-nitrobenzenesulfonamide protecting group. The naturally occurring toxins 1-5 representing each structural type have been efficiently synthesized by this method in a high overall yield with few steps. (C) 2002 Elsevier Science Ltd. All rights reserved.
• An efficient and versatile synthesis of all structural types of acylpolyamine spider toxins
  作者：Ken-ichi Nihei、Massuo J. Kato、Tetsuo Yamane、Katsuhiro Konno

  DOI：10.1016/j.tet.2006.06.051

  日期：2006.8

  An efficient and versatile synthesis of acylpolyamine spider toxins of all structural types classified by extensive MS analysis has been achieved. By using 2-nitrobenzenesulfonamide as an effective activating and/or protecting group (the Nosyl strategy), the naturally occurring toxins 1-8 corresponding to Types A-F were concisely synthesized in high overall yield. (c) 2006 Elsevier Ltd. All rights reserved.