3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside | 1521271-26-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(3,3-difluoroindol-2-yl)oxyoxan-2-yl]methyl benzoate
• CAS: 1521271-26-0
• 化学式: C₄₂H₃₁F₂NO₁₀
• 分子量: 747.706
• InChiKey: WCVAVOVWGRJKKP-ZNNRSBSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  55
• 可旋转键数：
  15
• 环数：
  7.0
• 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：
  13

反应信息

• 作为反应物：
  描述：

  3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside 、 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 0.08h， 以86%的产率得到1,2:3:4-di-O-isopropylidene-6-O-(tetra-O-benzoyl-β-D-glucopyranosyl)-α-D-galactose
  参考文献：
  名称：

  Regenerative Glycosylation under Nucleophilic Catalysis

  摘要：

  This article describes 3,3-difluoroxindole (HOFox)-mediated glycosylation. The uniqueness of this approach is that both the in situ synthesis of 3,3-difluoro-3H-indol-2-yl (OFox) glycosyl donors and activation thereof can be conducted in a regenerative fashion as is a typical reaction performed under nucleophilic catalysis. Only a catalytic amount of the OFox imidate donor and a Lewis acid activator are present in the reaction medium. The OFox imidate donor is constantly regenerated upon its consumption until glycosyl acceptor has reacted.

  DOI：

  10.1021/ja411746a
• 作为产物：
  描述：

  靛红 在 二乙胺基三氟化硫 、 N,N-二异丙基乙胺 、 silver(l) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  Regenerative Glycosylation under Nucleophilic Catalysis

  摘要：

  This article describes 3,3-difluoroxindole (HOFox)-mediated glycosylation. The uniqueness of this approach is that both the in situ synthesis of 3,3-difluoro-3H-indol-2-yl (OFox) glycosyl donors and activation thereof can be conducted in a regenerative fashion as is a typical reaction performed under nucleophilic catalysis. Only a catalytic amount of the OFox imidate donor and a Lewis acid activator are present in the reaction medium. The OFox imidate donor is constantly regenerated upon its consumption until glycosyl acceptor has reacted.

  DOI：

  10.1021/ja411746a

文献信息

• OFox imidates as versatile glycosyl donors for chemical glycosylation
  作者：Swati S. Nigudkar、Tinghua Wang、Salvatore G. Pistorio、Jagodige P. Yasomanee、Keith J. Stine、Alexei V. Demchenko

  DOI：10.1039/c6ob02230h

  日期：——

  mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study with the main focus on the synthesis of various OFox imidates and their investigation as glycosyl donors for chemical

  以前，我们交流了3,3-二氟己二酮（HOFox）介导的糖基化作用，其中发现3,3-二氟-3 H-吲哚-2-基（OFox）酰亚胺化是关键中间体。无论是在原位由相应的糖基溴化物和亚胺酸酯OFox活化合成可以在再生的方式进行。在这里，我们扩展了这项研究，主要侧重于各种OFox酰亚胺的合成及其作为化学1,2-顺式和1,2-反式糖基化的糖基供体的研究。