2,3,4-tri-O-benzoyl-6-O-(chloroacetyl)-α-D-mannopyranosyl fluoride | 1005398-15-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4-tri-O-benzoyl-6-O-(chloroacetyl)-α-D-mannopyranosyl fluoride
• 英文别名: [(2R,3R,4S,5S,6R)-4,5-dibenzoyloxy-2-[(2-chloroacetyl)oxymethyl]-6-fluorooxan-3-yl] benzoate
• CAS: 1005398-15-1
• 化学式: C₂₉H₂₄ClFO₉
• 分子量: 570.956
• InChiKey: WJBIARUQVAWJEI-MQNYBYKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-甲基咪唑 、 2,3,4-tri-O-benzoyl-6-O-(chloroacetyl)-α-D-mannopyranosyl fluoride 在 六氟磷酸钾 作用下， 以 乙腈 为溶剂， 以82%的产率得到1-methyl-3-(2-oxo-2-(((2R,3R,4S,5S,6R)-3,4,5-tris(benzoyloxy)-6-fluorotetrahydro-2H-pyran-2-yl)methoxy)ethyl)-1H-imidazol-3-ium hexafluorophosphate(V)
  参考文献：
  名称：

  Oligomannan Synthesis Using Ionic Liquid Supported Glycosylation

  摘要：

  The synthesis of complex oligosaccharides has been a challenge for researchers. Herein, we describe a strategy for the synthesis of an activated oligomannan 1 that employs ionic liquid (IL) support glycosylation methodology on an IL-tagged mannosyl fluoride donor. This method is capable of rapidly producing linear alpha(1 -> 6) oligomannan thioglycosides in a convenient and cost-effective manner without the need of column purification after each glycosylation step.

  DOI：

  10.1021/ol702743x
• 作为产物：
  描述：

  2,3,4-tri-O-benzoyl-α-D-mannopyranosyl fluoride 、 氯乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到2,3,4-tri-O-benzoyl-6-O-(chloroacetyl)-α-D-mannopyranosyl fluoride
  参考文献：
  名称：

  Oligomannan Synthesis Using Ionic Liquid Supported Glycosylation

  摘要：

  The synthesis of complex oligosaccharides has been a challenge for researchers. Herein, we describe a strategy for the synthesis of an activated oligomannan 1 that employs ionic liquid (IL) support glycosylation methodology on an IL-tagged mannosyl fluoride donor. This method is capable of rapidly producing linear alpha(1 -> 6) oligomannan thioglycosides in a convenient and cost-effective manner without the need of column purification after each glycosylation step.

  DOI：

  10.1021/ol702743x

文献信息

• Oligomannan Synthesis Using Ionic Liquid Supported Glycosylation
  作者：Ashish K. Pathak、Charu K. Yerneni、Zac Young、Vibha Pathak

  DOI：10.1021/ol702743x

  日期：2008.1.1

  The synthesis of complex oligosaccharides has been a challenge for researchers. Herein, we describe a strategy for the synthesis of an activated oligomannan 1 that employs ionic liquid (IL) support glycosylation methodology on an IL-tagged mannosyl fluoride donor. This method is capable of rapidly producing linear alpha(1 -> 6) oligomannan thioglycosides in a convenient and cost-effective manner without the need of column purification after each glycosylation step.