1,3,4,6-tetra-O-benzoyl-α,β-D-fructofuranosyl-2-(N-phenyl)-trifluoroacetimidate | 1093100-44-7

• 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: 1,3,4,6-tetra-O-benzoyl-α,β-D-fructofuranosyl-2-(N-phenyl)-trifluoroacetimidate
• 英文别名: [(2R,3R,4S)-3,4-dibenzoyloxy-5-(benzoyloxymethyl)-5-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxyoxolan-2-yl]methyl benzoate
• CAS: 1093100-44-7
• 化学式: C₄₂H₃₂F₃NO₁₀
• 分子量: 767.712
• InChiKey: NMWCDDXRAMXCIT-WNILVCJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  56
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-benzoyl-α,β-D-fructofuranosyl-2-(N-phenyl)-trifluoroacetimidate 、 双丙酮半乳糖 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到1,2:3,4-di-O-isopropylidene-6-O-(1,3,4,6-tetra-O-benzoyl-α-D-fructofuranosyl)-α-D-galactopyranose
  参考文献：
  名称：

  Synthesis of fructofuranosides: efficient glycosylation with N-phenyltrifluoroacetimidate as the leaving group

  摘要：

  Fructofuranosyl trifluoroacetimidate 3 was demonstrated to be an effective glycosyl donor that exhibited good alpha-selectivity and good yield in fructosylation reactions. The reaction proceeds via neighboring group participation, which was proved by the isolation of a stable allylic orthoester intermediate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.001
• 作为产物：
  描述：

  2,2,2-三氟-N-苯基亚氨代乙酰氯 、 1,3,4,6-tetra-O-benzoyl-D-fructofuranose 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以100%的产率得到1,3,4,6-tetra-O-benzoyl-α,β-D-fructofuranosyl-2-(N-phenyl)-trifluoroacetimidate
  参考文献：
  名称：

  Synthesis of fructofuranosides: efficient glycosylation with N-phenyltrifluoroacetimidate as the leaving group

  摘要：

  Fructofuranosyl trifluoroacetimidate 3 was demonstrated to be an effective glycosyl donor that exhibited good alpha-selectivity and good yield in fructosylation reactions. The reaction proceeds via neighboring group participation, which was proved by the isolation of a stable allylic orthoester intermediate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.001

文献信息

• Synthesis of fructofuranosides: efficient glycosylation with N-phenyltrifluoroacetimidate as the leaving group
  作者：Gaoyan Lian、Qi Gao、Feng Lin

  DOI：10.1016/j.carres.2008.09.001

  日期：2008.11

  Fructofuranosyl trifluoroacetimidate 3 was demonstrated to be an effective glycosyl donor that exhibited good alpha-selectivity and good yield in fructosylation reactions. The reaction proceeds via neighboring group participation, which was proved by the isolation of a stable allylic orthoester intermediate. (C) 2008 Elsevier Ltd. All rights reserved.