phenyl 2-O-benzyl-4,6-O-benzylidene-1-seleno-α-D-mannopyranoside | 221678-98-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: phenyl 2-O-benzyl-4,6-O-benzylidene-1-seleno-α-D-mannopyranoside
• CAS: 221678-98-4
• 化学式: C₂₆H₂₆O₅Se
• 分子量: 497.449
• InChiKey: VJRTXIUPAWJNJQ-DJZLDEFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-benzyl-4,6-O-benzylidene-1-seleno-α-D-mannopyranoside 在 palladium on activated charcoal 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 氨 、 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、358.53 kPa 条件下， 反应 22.17h， 生成 ethyl β-D-galactofuranosyl-(1->3)-α-D-mannopyranosyl-(1->2)-[β-D-galactofuranosyl-(1->3)]-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of galactofuranosyl-containing oligosaccharides corresponding to the glycosylinositolphospholipid of Trypanosomacruzi

  摘要：

  The oligosaccharide beta-D-Ga1f-(1-->3)-alpha-D-Manp-(1-->2)-[beta-D-Ga1f-(1-->3)]-alpha-D-Manp-(1-->2)-alpha-D-Manp corresponds to the terminal end of the glycosylinositolphospholipid oligosaccharide of the protozoan Trypanosoma cruzi, the causative agent of Chagas' disease. Syntheses of methyl or ethylthio glycosides of the terminal disaccharide, trisaccharide, tetrasaccharide, and pentasaccharide corresponding to this structure are described. These syntheses employ the selective activation of a phenyl 1-selenogalactofuranoside or a phenyl 1-selenomannopyranoside donor over ethyl 1-thioglycoside accepters with NIS-TfOH. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00007-0
• 作为产物：
  描述：

  phenyl 1-seleno-α-D-mannopyranoside 在 sodium hydroxide 、 四丁基硫酸氢铵 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.5h， 生成 phenyl 2-O-benzyl-4,6-O-benzylidene-1-seleno-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of galactofuranosyl-containing oligosaccharides corresponding to the glycosylinositolphospholipid of Trypanosomacruzi

  摘要：

  The oligosaccharide beta-D-Ga1f-(1-->3)-alpha-D-Manp-(1-->2)-[beta-D-Ga1f-(1-->3)]-alpha-D-Manp-(1-->2)-alpha-D-Manp corresponds to the terminal end of the glycosylinositolphospholipid oligosaccharide of the protozoan Trypanosoma cruzi, the causative agent of Chagas' disease. Syntheses of methyl or ethylthio glycosides of the terminal disaccharide, trisaccharide, tetrasaccharide, and pentasaccharide corresponding to this structure are described. These syntheses employ the selective activation of a phenyl 1-selenogalactofuranoside or a phenyl 1-selenomannopyranoside donor over ethyl 1-thioglycoside accepters with NIS-TfOH. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00007-0

文献信息

• Chemical synthesis of the N-glycans of gp63, the major surface glycoprotein from Leishmania mexicana amazonensis
  作者：Arno Düffels、Steven V. Ley

  DOI：10.1039/a809798d

  日期：——

  The chemical synthesis of the conjugated heptasaccharide Man(α1-3)Man(α1-6)[Glc(α1-3)Man(α1-2)Man(α1-2)Man(α1-3)]Manβ1-O[CH2]8CO2Me 1 and four closely related biantennary oligomannose type structures derived from the glycoprotein 63 of Leishmania mexicana amazonensis is described. Taking advantage of common structural motifs found in these N-glycans, a strategy based on the principles of reactivity tuning and orthogonal activation allowed the rapid assembly of a whole class of complex oligosaccharides. Deprotection of all structures was achieved in high yields by hydrogenolysis in one step.

  化学生成了共轭庚糖Man(α1-3)Man(α1-6)[Glc(α1-3)Man(α1-2)Man(α1-2)Man(α1-3)]Manβ1-O[CH2]8CO2Me 1以及四个与Leishmania mexicana amazonensis糖蛋白63衍生的双触角型寡甘露糖型结构密切相关的结构。利用这些N-聚糖中共有的结构特征，基于反应性调谐和正交激活原理的策略使得快速组装一整类复杂寡糖成为可能。所有结构的脱保护都能在一部氢解中高产率地完成。
• Dueffels, Arno; Green, Luke G.; Ley, Steven V., Chemistry - A European Journal, 2000, vol. 6, # 8, p. 1416 - 1430
  作者：Dueffels, Arno、Green, Luke G.、Ley, Steven V.、Miller, Andrew D.

  DOI：——

  日期：——