2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)acetic acid | 1251851-67-8

• 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,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)acetic acid
• CAS: 1251851-67-8
• 化学式: C₃₇H₃₈F₂O₈
• 分子量: 648.701
• InChiKey: JGTVMMFVXYTGMF-CQPYIVRQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  47.0
• 可旋转键数：
  16.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  92.68
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)acetic acid 、 N^α-fluoren-9-ylmethoxycarbonyl-L-ornithine benzyl ester hydrotrifluoroacetate 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以64%的产率得到(S)-benzyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(2,2-difluoro-2-((2R,3S,5S)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-methoxytetrahydro-2-H-pyran-2-yl)acetamido)pentanoate
  参考文献：
  名称：

  Assessing the ability of a short fluorinated antifreeze glycopeptide and a fluorinated carbohydrate derivative to inhibit ice recrystallization

  摘要：

  A short fluorinated antifreeze glycopeptide (2) was synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The activity of 2 was compared to native biological antifreeze AFGP 8 and a rationally designed C-linked AFGP analogue (OGG-Gal, 1). In addition, a simple fluorinated galactose derivative was prepared and its IRI activity was compared to non-fluorinated compounds. The results from this study suggest that the stereochemistry at the anomeric position in the carbohydrate plays a role in imparting ice recrystallization inhibition activity and that incorporation of hydrophobic groups such as fluorine atoms cause a decrease in IRI activity. These observations are consistent with the theory that fluorine atoms increase ordering of bulk water resulting in a decrease of IRI activity, supporting our previously proposed mechanism of ice recrystallization inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.148
• 作为产物：
  描述：

  ethyl 2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)acetate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 以78%的产率得到2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methoxytetrahydro-2H-pyran-2-yl)acetic acid
  参考文献：
  名称：

  Assessing the ability of a short fluorinated antifreeze glycopeptide and a fluorinated carbohydrate derivative to inhibit ice recrystallization

  摘要：

  A short fluorinated antifreeze glycopeptide (2) was synthesized and evaluated for ice recrystallization inhibition (IRI) activity. The activity of 2 was compared to native biological antifreeze AFGP 8 and a rationally designed C-linked AFGP analogue (OGG-Gal, 1). In addition, a simple fluorinated galactose derivative was prepared and its IRI activity was compared to non-fluorinated compounds. The results from this study suggest that the stereochemistry at the anomeric position in the carbohydrate plays a role in imparting ice recrystallization inhibition activity and that incorporation of hydrophobic groups such as fluorine atoms cause a decrease in IRI activity. These observations are consistent with the theory that fluorine atoms increase ordering of bulk water resulting in a decrease of IRI activity, supporting our previously proposed mechanism of ice recrystallization inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.148