methyl 2-((2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetate | 1251851-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-((2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetate
• CAS: 1251851-64-5
• 化学式: C₉H₁₆O₈
• 分子量: 252.221
• InChiKey: WPIGPZNOKVYZFB-MRCFXUCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.29
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  136.68
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  methyl (4,5,6,8-tetra-O-benzyl-2-deoxy-α-D-galacto-3-octulopyranosid)onate 在 palladium on carbon 、 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以100%的产率得到methyl 2-((2S,3R,4S,5R,6R)-2,3,4,5-tetrahydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetate
  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