N-(2,2-difluoro-2-(α-D-mannopyranosyl)acetyl)-L-glutamic acid | 1014698-45-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(2,2-difluoro-2-(α-D-mannopyranosyl)acetyl)-L-glutamic acid
• 英文别名: (S)-2-(2,2-difluoro-2-((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)acetamido)pentanedioic acid；(2S)-2-[[2,2-difluoro-2-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetyl]amino]pentanedioic acid
• CAS: 1014698-45-3
• 化学式: C₁₃H₁₉F₂NO₁₀
• 分子量: 387.291
• InChiKey: JFSFGSLQUPPTQC-FQXPNUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  194
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 以100%的产率得到N-(2,2-difluoro-2-(α-D-mannopyranosyl)acetyl)-L-glutamic acid
  参考文献：
  名称：

  Synthesis of α-CF₂-mannosides and Their Conversion to Fluorinated Pseudoglycopeptides

  摘要：

  A methodology allowing the synthesis alpha-CF(2)-rnannosides, based on the addition of a difluoroenoxysilane to a glycal followed by a dihydroxylation reaction, is described. The resulting 2,2-difluoro-2-mannosylacetate is converted into two pseudoglycopeptides which may act as E- and P-selectin inhibitors.

  DOI：

  10.1021/jo702466h

文献信息

• Synthesis of α-CF₂-mannosides and Their Conversion to Fluorinated Pseudoglycopeptides
  作者：Florent Poulain、Anne-Lise Serre、Jérôme Lalot、Eric Leclerc、Jean-Charles Quirion

  DOI：10.1021/jo702466h

  日期：2008.3.1

  A methodology allowing the synthesis alpha-CF(2)-rnannosides, based on the addition of a difluoroenoxysilane to a glycal followed by a dihydroxylation reaction, is described. The resulting 2,2-difluoro-2-mannosylacetate is converted into two pseudoglycopeptides which may act as E- and P-selectin inhibitors.