ethyl 2-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)-2,2-difluoroacetate | 1014698-40-8

• 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: ethyl 2-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)-2,2-difluoroacetate
• 英文别名: ethyl 2-[(2R,3S)-3-acetyloxy-2-(acetyloxymethyl)-3,6-dihydro-2H-pyran-6-yl]-2,2-difluoroacetate
• CAS: 1014698-40-8
• 化学式: C₁₄H₁₈F₂O₇
• 分子量: 336.29
• InChiKey: LUYGIHCYOAKLCX-WIKAKEFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  ethyltrimethylsilyl-2,2-difluoroketene acetal 、 乙酰化葡萄烯糖 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到ethyl 2-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)-2,2-difluoroacetate
  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