O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl fluoride | 1330533-94-2

• 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: O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl fluoride
• 英文别名: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Glc(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Glc(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]Glc(b1-6)[Bz(-2)][Bz(-3)][Bz(-4)]b-Glc1F；[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[[(2R,3R,4S,5R,6S)-3,4,5-tribenzoyloxy-6-fluorooxan-2-yl]methoxy]oxan-2-yl]methoxy]oxan-2-yl]methoxy]oxan-2-yl]methyl benzoate
• CAS: 1330533-94-2
• 化学式: C₁₁₅H₉₃FO₃₃
• 分子量: 2021.98
• InChiKey: ZSBQBPWVQLFJHY-KEWBKQTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.5
• 重原子数：
  149
• 可旋转键数：
  49
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  407
• 氢给体数：
  0
• 氢受体数：
  34

反应信息

• 作为反应物：
  描述：

  O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl fluoride 、 ethyl 2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 在 二氯二茂锆 、 silver perchlorate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 17.0h， 以84%的产率得到ethyl O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  On Orthogonal and Selective Activation of Glycosyl Thioimidates and Thioglycosides: Application to Oligosaccharide Assembly

  摘要：

  Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the activating reagent nor by the stability of the leaving group itself; instead, the type of activation plays the key role. The activation conditions established herein were applied to a sequential five-step synthesis of a hexasaccharide using six monosaccharide building blocks equipped with six different leaving groups.

  DOI：

  10.1021/jo201117s
• 作为产物：
  描述：

  2-benzoxazolyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 、 2,3,4-tri-O-benzoyl-β-D-glucopyranosyl fluoride 在 三氟甲烷磺酸甲酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以87%的产率得到O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl fluoride
  参考文献：
  名称：

  On Orthogonal and Selective Activation of Glycosyl Thioimidates and Thioglycosides: Application to Oligosaccharide Assembly

  摘要：

  Discrimination among S-thiazolinyl (STaz), S-benzoxazolyl (SBox), and S-ethyl anomeric leaving groups was achieved by fine-tuning activation conditions. Preferential glycosidation of a certain leaving group is determined neither by the strength of the activating reagent nor by the stability of the leaving group itself; instead, the type of activation plays the key role. The activation conditions established herein were applied to a sequential five-step synthesis of a hexasaccharide using six monosaccharide building blocks equipped with six different leaving groups.

  DOI：

  10.1021/jo201117s