2,3,5-tri-O-benzoyl-D-ribofuranosyl(N-phenyl)trifluoroacetimidate | 1055317-41-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzoyl-D-ribofuranosyl(N-phenyl)trifluoroacetimidate
• 英文别名: [(2R,3R,4R)-3,4-dibenzoyloxy-5-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxyoxolan-2-yl]methyl benzoate
• CAS: 1055317-41-3
• 化学式: C₃₄H₂₆F₃NO₈
• 分子量: 633.578
• InChiKey: YTBLPSBWODIXKS-ODYACQGXSA-N

物化性质

• 沸点：
  668.5±65.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 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-benzoyl-D-ribofuranosyl(N-phenyl)trifluoroacetimidate 、 胸腺嘧啶 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 、 1,2-二氯乙烷 为溶剂， 反应 0.5h， 以88%的产率得到2',3',5'-tri-O-benzoyluridine
  参考文献：
  名称：

  Effective synthesis of nucleosides with glycosyl trifluoroacetimidates as donors

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2008.06.042

文献信息

• An improved procedure for nucleoside synthesis using glycosyl trifluoroacetimidates as donors
  作者：Jinxi Liao、Jiansong Sun、Biao Yu

  DOI：10.1016/j.carres.2009.03.010

  日期：2009.5

  Using glycosyl trifluoroacetimidates as donors and nitromethane (or acetonitrile) as solvent, silylation and subsequent glycosylation were realized in a 'one-pot' procedure to provide the corresponding nucleosides derivatives in high yields.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.
• 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.