ethyl 2,2-difluoro-2-[(2R,3S)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-6-yl]acetate | 1030595-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ethyl 2,2-difluoro-2-[(2R,3S)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-6-yl]acetate
• CAS: 1030595-58-4
• 化学式: C₁₀H₁₄F₂O₅
• 分子量: 252.215
• InChiKey: IFOSCKONNOEMBQ-KJFJCRTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2,2-difluoro-2-[(2R,3S)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-6-yl]acetate 在 Oxone 、 乙二胺四乙酸 、 1,1,1-三氟丙酮 、 碳酸氢钠 作用下， 以 水 、 乙腈 为溶剂， 以64%的产率得到ethyl 2,2-difluoro-2-[(4R,5R)-5-hydroxy-4-(hydroxymethyl)-3,7-dioxabicyclo[4.1.0]heptan-2-yl]acetate
  参考文献：
  名称：

  Approaches to the synthesis of CF2-analogues of 2-deoxy-2-aminoglycosides

  摘要：

  The preparation of a fluorinated C-glycosidic analogue of a 2-deoxy-2-acetamido-D-altrose is described. The synthetic sequence involves the addition of a difluoroenoxysilane to a D-glucal, an epoxidation of the resulting unsaturated CF2-glycoside and a ring-opening reaction with TMSN3. An Overman rearrangement of the unsaturated intermediate is also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.01.155
• 作为产物：
  描述：

  ethyl 2-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)-2,2-difluoroacetate 在 乙酰氯 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 ethyl 2,2-difluoro-2-[(2R,3S)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-6-yl]acetate
  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.
• Approaches to the synthesis of CF2-analogues of 2-deoxy-2-aminoglycosides
  作者：Florent Poulain、Eric Leclerc、Jean-Charles Quirion

  DOI：10.1016/j.tetlet.2009.01.155

  日期：2009.4

  The preparation of a fluorinated C-glycosidic analogue of a 2-deoxy-2-acetamido-D-altrose is described. The synthetic sequence involves the addition of a difluoroenoxysilane to a D-glucal, an epoxidation of the resulting unsaturated CF2-glycoside and a ring-opening reaction with TMSN3. An Overman rearrangement of the unsaturated intermediate is also described. (C) 2009 Elsevier Ltd. All rights reserved.