2,4,6-trinitrophenyl 2-deoxy-2,2-difluoro-α-D-arabinohexopyranoside | 172100-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-trinitrophenyl 2-deoxy-2,2-difluoro-α-D-arabinohexopyranoside
• 英文别名: 2,4,6-Trinitrophenyl 2,2-difluoro-2-deoxy-alpha-D-glucopyranoside；(2R,3S,4S,6R)-5,5-difluoro-2-(hydroxymethyl)-6-(2,4,6-trinitrophenoxy)oxane-3,4-diol
• CAS: 172100-33-3
• 化学式: C₁₂H₁₁F₂N₃O₁₁
• 分子量: 411.23
• InChiKey: BOLHDBMFIBYDDA-DEKFOEGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  217
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  2,4,6-trinitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2,2-difluoro-α-D-arabinohexopyranoside 在 甲醇 、 乙酰氯 作用下， 以19%的产率得到2,4,6-trinitrophenyl 2-deoxy-2,2-difluoro-α-D-arabinohexopyranoside
  参考文献：
  名称：

  2-脱氧-2,2-二卤代糖苷作为α-糖苷酶机制抑制剂的合成和测试

  摘要：

  一系列2-脱氧-2,2-二卤代糖基卤化物作为潜在的α-糖苷酶失活剂的合成已经通过保护的2-氟糖基前体的卤化来实现。per-的直接氯化ö -acetylated 2-氟d -glucal和2- fluoromaltal随后基本去保护，产生相应的2-氯-2-脱氧-2- fluoroglycosyl氯化物。per- O的反应用乙酰基次萤石或Selectfluor对乙酰基化的2-氟代糖生成2-脱氧-2,2-二氟代糖基衍生物，使用亚硫酰氯将其转化为α-氯化物，并在碱性条件下脱保护。通过使半缩醛与吡啶甲基氟进行芳基化反应，合成2-脱氧-2,2-二氟单糖和二糖的三硝基苯基糖苷，然后在甲醇中用HCl脱保护。所有三种单糖衍生物均通过以下途径引起酵母α-葡萄糖苷酶的活性定点时间依赖性失活确定了共价糖基酶中间体的捕集，以及每种化合物灭活的动力学参数。出乎意料的是，尽管三硝基苯基2-脱氧-2,2-二氟麦芽糖苷以这种方式起作用，但2-脱氧-2

  DOI：

  10.1021/jo702565q

文献信息

• COMPOSITIONS FOR CANCER TREATMENT
  申请人：Engene, Inc.

  公开号：EP1556088A2

  公开（公告）日：2005-07-27
• Cancer treatment by metabolic modulations
  申请人：Pownall Scott

  公开号：US20050202559A1

  公开（公告）日：2005-09-15

  The invention provides compositions and methods for inhibiting the growth or proliferation of hyperproliferative cells or inducing regression of hyperproliferative cells. More specifically, the invention provides compositions and methods for stimulating glycogen accumulation in target cells (e.g., hyperproliferative cells) in order to increase glycogen to a level that is toxic to the target cell.
• CANCER TREATMENT BY METABOLIC MODULATIONS
  申请人：POWNALL SCOTT

  公开号：US20090041740A1

  公开（公告）日：2009-02-12

  The invention provides compositions and methods for inhibiting the growth or proliferation of hyperproliferative cells or inducing regression of hyperproliferative cells. More specifically, the invention provides compositions and methods for stimulating glycogen accumulation in target cells (e.g., hyperproliferative cells) in order to increase glycogen to a level that is toxic to the target cell.
• [EN] CANCER TREATMENT BY METABOLIC MODULATIONS<br/>[FR] TRAITEMENT DE CANCER PAR DES MODULATIONS METABOLIQUES
  申请人：ENGENE INC

  公开号：WO2004039412A2

  公开（公告）日：2004-05-13

  The invention provides compositions and methods for inhibiting the growth or proliferation of hyperproliferative cells or inducing regression of hyperproliferative cells. More specifically, the invention provides compositions and methods for stimulating glycogen accumulation in target cells (e.g., hyperproliferative cells) in order to increase glycogen to a level that is toxic to the target cell.
• Synthesis and Testing of 2-Deoxy-2,2-Dihaloglycosides as Mechanism-Based Inhibitors of α-Glycosidases
  作者：Ran Zhang、John D. McCarter、Curtis Braun、Wai Yeung、Gary D. Brayer、Stephen G. Withers

  DOI：10.1021/jo702565q

  日期：2008.4.1

  yielded the corresponding 2-chloro-2-deoxy-2-fluoroglycosyl chlorides. Reaction of the per-O-acetylated 2-fluoroglycals with acetyl hypofluorite or Selectfluor yielded the 2-deoxy-2,2-difluoroglycosyl derivatives, which were converted to their α-chlorides using thionyl chloride and deprotected under basic conditions. Trinitrophenyl glycosides of the 2-deoxy-2,2-difluoro mono- and disaccharides were

  一系列2-脱氧-2,2-二卤代糖基卤化物作为潜在的α-糖苷酶失活剂的合成已经通过保护的2-氟糖基前体的卤化来实现。per-的直接氯化ö -acetylated 2-氟d -glucal和2- fluoromaltal随后基本去保护，产生相应的2-氯-2-脱氧-2- fluoroglycosyl氯化物。per- O的反应用乙酰基次萤石或Selectfluor对乙酰基化的2-氟代糖生成2-脱氧-2,2-二氟代糖基衍生物，使用亚硫酰氯将其转化为α-氯化物，并在碱性条件下脱保护。通过使半缩醛与吡啶甲基氟进行芳基化反应，合成2-脱氧-2,2-二氟单糖和二糖的三硝基苯基糖苷，然后在甲醇中用HCl脱保护。所有三种单糖衍生物均通过以下途径引起酵母α-葡萄糖苷酶的活性定点时间依赖性失活确定了共价糖基酶中间体的捕集，以及每种化合物灭活的动力学参数。出乎意料的是，尽管三硝基苯基2-脱氧-2,2-二氟麦芽糖苷以这种方式起作用，但2-脱氧-2