3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside | 1521271-24-8

• 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-acetyl-α-D-glucopyranoside
• CAS: 1521271-24-8
• 化学式: C₂₂H₂₃F₂NO₁₀
• 分子量: 499.422
• InChiKey: OMIOJRNTAWEULO-OUUBHVDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  136.02
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以80%的产率得到methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-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
• 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 甲苯 为溶剂， 反应 6.0h， 生成 3,3-difluoro-3H-indol-2-yl 2,3,4,6-tetra-O-acetyl-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。