2,2-difluoro-2-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-hydroxytetrahydro-2H-pyran-2-yl)acetic acid | 1224632-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-difluoro-2-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-hydroxytetrahydro-2H-pyran-2-yl)acetic acid
• CAS: 1224632-62-5
• 化学式: C₃₆H₃₆F₂O₈
• 分子量: 634.674
• InChiKey: ZYMRQERGOGDQRA-UCFOWLENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  46.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  103.68
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  dibenzyl L-glutamate 、 2,2-difluoro-2-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-hydroxytetrahydro-2H-pyran-2-yl)acetic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以53%的产率得到
  参考文献：
  名称：

  Synthesis of fluorinated C-mannopeptides as sialyl Lewisx mimics for E- and P-selectin inhibition

  摘要：

  The synthesis of fluorinated C-mannopeptides and their evaluation as E- and P-selectin inhibitors is described. These molecules are difluorinated analogues of CH2-glycopeptides already reported to act as sLe(x) mimics. The alpha and beta anomers of these CF2-glycopeptides have been prepared, as well as their 1-hydroxy analogues which were present in solution as an equilibrium mixture of alpha- and beta-pyranose and alpha- and beta-furanose forms. These molecules showed inhibitory activities comparable to their CH2 counterparts with a moderate influence of the pseudo-anomeric center configuration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.141
• 作为产物：
  描述：

  Difluoro-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid ethyl ester 在 lithium hydroxide 作用下， 以91%的产率得到2,2-difluoro-2-((2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-hydroxytetrahydro-2H-pyran-2-yl)acetic acid
  参考文献：
  名称：

  Synthesis of fluorinated C-mannopeptides as sialyl Lewisx mimics for E- and P-selectin inhibition

  摘要：

  The synthesis of fluorinated C-mannopeptides and their evaluation as E- and P-selectin inhibitors is described. These molecules are difluorinated analogues of CH2-glycopeptides already reported to act as sLe(x) mimics. The alpha and beta anomers of these CF2-glycopeptides have been prepared, as well as their 1-hydroxy analogues which were present in solution as an equilibrium mixture of alpha- and beta-pyranose and alpha- and beta-furanose forms. These molecules showed inhibitory activities comparable to their CH2 counterparts with a moderate influence of the pseudo-anomeric center configuration. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.141