ethyl 2-(6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-2,2-difluoroacetate | 1014698-41-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-2,2-difluoroacetate
• 英文别名: ethyl 2-[(2S,3S,4S,5S,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]-2,2-difluoroacetate
• CAS: 1014698-41-9
• 化学式: C₂₆H₃₄F₂O₇Si
• 分子量: 524.634
• InChiKey: VKKQBBDRIZHRMZ-VROINQGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  ethyl 2-(6-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-2,2-difluoroacetate 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 二氯甲烷 、 水 为溶剂， 以62%的产率得到ethyl 2-(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

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.