4,7-anhydro-1,3-dideoxy-5,6-O-isopropylidene-8-O-trityl-D-allo-oct-2-ulose | 86563-06-6

• 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: 4,7-anhydro-1,3-dideoxy-5,6-O-isopropylidene-8-O-trityl-D-allo-oct-2-ulose
• 英文别名: 1-[(3aR,4R,6S,6aS)-2,2-dimethyl-4-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]propan-2-one
• CAS: 86563-06-6
• 化学式: C₃₀H₃₂O₅
• 分子量: 472.581
• InChiKey: YKMOIYSDMCOSFC-ZVBOOHQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,7-anhydro-1,3-dideoxy-5,6-O-isopropylidene-8-O-trityl-D-allo-oct-2-ulose 在 ammonium formate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以98%的产率得到4,7-anhydro-2-amino-1,2,3-trideoxy-5,6-O-isopropylidene-8-O-trityl-D-allo-octitol
  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：

  5-O-三苯甲基-2,3-O-异亚丙基-D-呋喃核糖 、 1-三苯基膦-2-丙酮 以 甲苯 为溶剂， 反应 3.0h， 以46%的产率得到4,7-anhydro-1,3-dideoxy-5,6-O-isopropylidene-8-O-trityl-D-allo-oct-2-ulose
  参考文献：
  名称：

  Synthesis of carbon 1 C-.beta.-D-ribofuranosyl derivatives with a highly functionalized two-carbon unit. Conversion to certain blocked thiazole C-nucleosides

  摘要：

  DOI：

  10.1021/jo00167a001

文献信息

• Synthesis of carbon 1 C-.beta.-D-ribofuranosyl derivatives with a highly functionalized two-carbon unit. Conversion to certain blocked thiazole C-nucleosides
  作者：Michael C. Clingerman、John A. Secrist

  DOI：10.1021/jo00167a001

  日期：1983.9
• Synthesis and biochemical evaluation of guanidino-alkyl-ribitol derivatives as nucleoside hydrolase inhibitors
  作者：A. Goeminne、M. McNaughton、G. Bal、G. Surpateanu、P. Van Der Veken、S. De Prol、W. Versées、J. Steyaert、A. Haemers、K. Augustyns

  DOI：10.1016/j.ejmech.2007.03.027

  日期：2008.2

  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.