2,3,5-tri-O-acetyl-D-ribofuranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate | 942428-91-3

• 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: 2,3,5-tri-O-acetyl-D-ribofuranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate
• 英文别名: 2,3,5-tri-O-acetyl-D-ribofuranosyl(N-phenyl)trifluoroacetimidate；[(2R,3R,4R)-3,4-diacetyloxy-5-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxyoxolan-2-yl]methyl acetate
• CAS: 942428-91-3
• 化学式: C₁₉H₂₀F₃NO₈
• 分子量: 447.365
• InChiKey: KGIYFNGKDDGIKJ-HJNZIYBASA-N

物化性质

• 熔点：
  66.1 °C
• 沸点：
  455.1±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-acetyl-D-ribofuranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 、 伏立诺他 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到2,3,5-tri-O-acetyl-1-O-7-(phenylcarbamoyl)hepthydroxamoyl-β-D-ribofuranose
  参考文献：
  名称：

  First O-Glycosylation of Hydroxamic Acids

  摘要：

  The first O-glycosylation of hydroxamic acids is reported. This process involves the use of glycosyl N-phenyl trifluoroacetimidates as glycosyl donors in the presence TMSOTf and 4 angstrom molecular sieves in dichloromethane. Under such conditions, a wide range of new glycosyl donors including glucosyl, galactosyl, mannosyl, glucuronyl, and ribosyl hydroxamates were prepared in good to high yields. This procedure appears to be an advantageous alternative for the synthesis of glycosyl hydroxamates of biological interest.

  DOI：

  10.1021/jo0701839
• 作为产物：
  描述：

  2,3,5-tri-O-acetyl-D-ribofuranose 、 2,2,2-三氟-N-苯基亚氨代乙酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到2,3,5-tri-O-acetyl-D-ribofuranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate
  参考文献：
  名称：

  First O-Glycosylation of Hydroxamic Acids

  摘要：

  The first O-glycosylation of hydroxamic acids is reported. This process involves the use of glycosyl N-phenyl trifluoroacetimidates as glycosyl donors in the presence TMSOTf and 4 angstrom molecular sieves in dichloromethane. Under such conditions, a wide range of new glycosyl donors including glucosyl, galactosyl, mannosyl, glucuronyl, and ribosyl hydroxamates were prepared in good to high yields. This procedure appears to be an advantageous alternative for the synthesis of glycosyl hydroxamates of biological interest.

  DOI：

  10.1021/jo0701839

文献信息

• Effective synthesis of nucleosides with glycosyl trifluoroacetimidates as donors
  作者：Jinxi Liao、Jiansong Sun、Biao Yu

  DOI：10.1016/j.tetlet.2008.06.042

  日期：2008.8

  Glycosyl trifluoroacetimidates have been disclosed to be effective glycosyl donors for the synthesis of nucleosides; the present N-glycosylation protocol requires only a catalytic amount of TMSOTf as promoter and proceeds smoothly at room temperature. (c) 2008 Elsevier Ltd. All rights reserved.