3,6-anhydro-1-amino-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol | 1020107-18-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3,6-anhydro-1-amino-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol
• 英文别名: 2-[(3aR,4R,6S,6aS)-2,2-dimethyl-4-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]ethanamine
• CAS: 1020107-18-9
• 化学式: C₂₉H₃₃NO₄
• 分子量: 459.585
• InChiKey: SIJSVONROKPMGV-YYGZZXRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,6-anhydro-1-amino-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol 、 1-[(tert-butyloxycarbonylamino)-(tert-butyloxycarbonylimino)-methyl]-1H-pyrazole 以 氯仿 为溶剂， 反应 24.0h， 以94%的产率得到N,N'-bis(tert-butoxycarbonyl)-1-guanidino-3,6-anhydro-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol
  参考文献：
  名称：

  Synthesis and biochemical evaluation of guanidino-alkyl-ribitol derivatives as nucleoside hydrolase inhibitors

  摘要：

  Nucleoside hydrolase (NH) is a key enzyme in the purine salvage pathway. The purine specificity of the IAG-NH from Trypanosoma vivax is at least in part due to cation-pi-stacking interactions. Guanidinium ions can be involved in cation-pi-stacking interactions, therefore a series of guanidino-alkyl-ribitol derivatives were synthesized in order to examine the binding affinity of these compounds towards the target enzyme. The compounds show moderate to good inhibiting activity towards the IAG-NH from T. vivax. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.027
• 作为产物：
  描述：

  3,6-anhydro-1-azido-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以92%的产率得到3,6-anhydro-1-amino-1,2-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-allo-heptitol
  参考文献：
  名称：

  Synthesis and biochemical evaluation of guanidino-alkyl-ribitol derivatives as nucleoside hydrolase inhibitors

  摘要：

  Nucleoside hydrolase (NH) is a key enzyme in the purine salvage pathway. The purine specificity of the IAG-NH from Trypanosoma vivax is at least in part due to cation-pi-stacking interactions. Guanidinium ions can be involved in cation-pi-stacking interactions, therefore a series of guanidino-alkyl-ribitol derivatives were synthesized in order to examine the binding affinity of these compounds towards the target enzyme. The compounds show moderate to good inhibiting activity towards the IAG-NH from T. vivax. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.03.027