tert-butyl (2S,3R)-3-(benzyloxy)-1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-1-oxobutan-2-ylcarbamate | 1380092-29-4

• 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: tert-butyl (2S,3R)-3-(benzyloxy)-1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-1-oxobutan-2-ylcarbamate
• 英文别名: tert-butyl N-[(2S,3R)-1-[(2-hydroxy-3,5,6-trimethoxyphenyl)methylamino]-1-oxo-3-phenylmethoxybutan-2-yl]carbamate
• CAS: 1380092-29-4
• 化学式: C₂₆H₃₆N₂O₈
• 分子量: 504.58
• InChiKey: FTVAPPIPEOTJPT-IERDGZPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3R)-3-(benzyloxy)-1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-1-oxobutan-2-ylcarbamate 在 碘苯二乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 0.25h， 以68%的产率得到tert-butyl (2S,3R)-3-(benzyloxy)-1-((2,5-dimethoxy-3,6-dioxocyclohexa-1,4-dienyl)methylamino)-1-oxobutan-2-ylcarbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of hydrophilic embelin derivatives

  摘要：

  In continuance of our search for newer anti-cancer agents we were interested on embelin, a XIAP (X-linked inhibitor of apoptosis protein) inhibitor. This natural benzoquinone bear a lipophilic chain and we report here the synthesis of hydrophilic analogues of embelin. To allow a large flexibility in the nature of the hydrophilic group, three amines with different length of carbon chain bearing a protected benzoquinone were prepared. The cytotoxic effects of these derivatives were evaluated on KB cell line. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.024
• 作为产物：
  描述：

  2,4,5-三甲氧基苯甲醛 在 t-butyldimethylsilane 、 间氯过氧苯甲酸 、 三氟乙酸 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 44.5h， 生成 tert-butyl (2S,3R)-3-(benzyloxy)-1-(2-hydroxy-3,5,6-trimethoxybenzylamino)-1-oxobutan-2-ylcarbamate
  参考文献：
  名称：

  Synthesis and biological evaluation of hydrophilic embelin derivatives

  摘要：

  In continuance of our search for newer anti-cancer agents we were interested on embelin, a XIAP (X-linked inhibitor of apoptosis protein) inhibitor. This natural benzoquinone bear a lipophilic chain and we report here the synthesis of hydrophilic analogues of embelin. To allow a large flexibility in the nature of the hydrophilic group, three amines with different length of carbon chain bearing a protected benzoquinone were prepared. The cytotoxic effects of these derivatives were evaluated on KB cell line. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.024