ethyl 2-(6-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)-2,2-difluoroacetate | 1014698-47-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ethyl 2-(6-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)-2,2-difluoroacetate
• 英文别名: ethyl 2-[(2R,3S,6R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-3,6-dihydro-2H-pyran-6-yl]-2,2-difluoroacetate
• CAS: 1014698-47-5
• 化学式: C₂₆H₃₂F₂O₅Si
• 分子量: 490.619
• InChiKey: JQHVIIFZNIIFBI-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-(6-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl)-2,2-difluoroacetate 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86%的产率得到
  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 2,2-difluoro-2-[(2R,3S)-3-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-6-yl]acetate 、 叔丁基二苯基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以665 mg的产率得到ethyl 2-(6-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-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.
• 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.