(1R,2R,3R,4S)-1-azido-4-[N-(tert-butyloxycarbonyl)amino]-1-(4-nitrophenyl)-5-phenylpentane-2,3-diol | 742107-32-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (1R,2R,3R,4S)-1-azido-4-[N-(tert-butyloxycarbonyl)amino]-1-(4-nitrophenyl)-5-phenylpentane-2,3-diol
• CAS: 742107-32-0
• 化学式: C₂₂H₂₇N₅O₆
• 分子量: 457.486
• InChiKey: IFHGNISGUNCMBY-MTQWCTHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  170.69
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3R,4S)-1-azido-4-[N-(tert-butyloxycarbonyl)amino]-1-(4-nitrophenyl)-5-phenylpentane-2,3-diol 在 水 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 49.0h， 生成 (S)-1-{(4R,5R)-5-[(R)-amino-(4-nitrophenyl)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-N-(tert-butyloxycarbonyl)-2-phenylethylamine
  参考文献：
  名称：

  Stereoselective synthesis of a novel pseudopeptide hapten for the generation of hydrolytic catalytic antibodies

  摘要：

  The synthesis of a novel hapten containing a 1,4-diamino-2,3-diolbutane core unit is described. The molecule contains four stereogenic centres and has been synthesised via a stereoselective route. The absolute stereochemistry of each stereogenic carbon atom has been assigned by nuclear Overhauser effect experiments carried out on a number of derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.005
• 作为产物：
  描述：

  (1S,2S,3R,4S)-4-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-1-(4-nitrophenyl)-5-phenylpentan-3-ol 在 sodium azide 、 氯化铵 作用下， 以 水 、 丙酮 为溶剂， 反应 30.0h， 以80%的产率得到(1R,2R,3R,4S)-1-azido-4-[N-(tert-butyloxycarbonyl)amino]-1-(4-nitrophenyl)-5-phenylpentane-2,3-diol
  参考文献：
  名称：

  Stereoselective synthesis of a novel pseudopeptide hapten for the generation of hydrolytic catalytic antibodies

  摘要：

  The synthesis of a novel hapten containing a 1,4-diamino-2,3-diolbutane core unit is described. The molecule contains four stereogenic centres and has been synthesised via a stereoselective route. The absolute stereochemistry of each stereogenic carbon atom has been assigned by nuclear Overhauser effect experiments carried out on a number of derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.05.005