phenyl 4,6-O-benzylidene-1-seleno-α-D-mannopyranoside | 282088-46-4

• 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 4,6-O-benzylidene-1-seleno-α-D-mannopyranoside
• 英文别名: (2R,4aR,6R,7S,8R,8aS)-2-phenyl-6-phenylselanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 282088-46-4
• 化学式: C₁₉H₂₀O₅Se
• 分子量: 407.325
• InChiKey: BESATBIFTAYNCA-RPVYPSMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-O-benzylidene-1-seleno-α-D-mannopyranoside 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 、 四丁基硫酸氢铵 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 42.17h， 生成 ethyl 2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl-(1->2)-[2,3,5,6-tetra-O-acetyl-β-D-galactofuranosyl-(1->3)]-4,6-O-benzylidene-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：

  Α-D-五乙酸甘露糖酯 在 sodium methylate 、 亚膦酸 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 phenyl 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