ethyl 2-(2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-2,2-difluoroacetate | 1014698-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-2,2-difluoroacetate
• CAS: 1014698-44-2
• 化学式: C₄₇H₅₂F₂O₇Si
• 分子量: 795.008
• InChiKey: GNXDPTUGMSNJEJ-JGWPTPRHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.29
• 重原子数：
  57.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  72.45
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-2,2-difluoroacetate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 3,7-anhydro-4,5,6-tri-O-benzyl-8-O-t-butyldiphenylsilyl-2,2-difluoro-D-glycero-D-talo-octosonic 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
• 作为产物：
  描述：

  benzyltrichloroacetimidate 、 ethyl 2-(6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-2,2-difluoroacetate 在 molecular sieve 、 三氟甲磺酸 作用下， 以 1,4-二氧六环 为溶剂， 以58%的产率得到ethyl 2-(2,3,4-tri-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-2,2-difluoroacetate
  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