phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-2-O-benzyl-4,6-benzylidene-α-D-mannopyranoside | 878806-04-3

• 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: phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-2-O-benzyl-4,6-benzylidene-α-D-mannopyranoside
• CAS: 878806-04-3
• 化学式: C₄₀H₄₄O₁₅
• 分子量: 764.78
• InChiKey: JXUWJLAWANEFLT-GBPCLQFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  55.0
• 可旋转键数：
  13.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  169.81
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-2-O-benzyl-4,6-benzylidene-α-D-mannopyranoside 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 5.25h， 生成 phenyl-α-D-mannopyranosyl-(1->3)-α-D-mannopyranoside
  参考文献：
  名称：

  Building Up Key Segments of N-Glycans in the Gas Phase:  Intrinsic Structural Preferences of the α(1,3) and α(1,6) Dimannosides

  摘要：

  The intrinsic conformer specific vibrational spectra of two important subunits of the core pentasaccharide of Winked glycans, the alpha(1,3) and alpha(1,6) dimannosides, have been recorded in the gas phase. Coupling these measurements with a computational exploration of their conformational landscapes has enabled their conformational assignment and has identified characteristic vibrational signatures associated with particular conformational families-including those that do or do not display inter-ring hydrogen bonding across the glycosidic linkage. In addition, the IR spectra of the monosaccharide moieties provide benchmarks, through which the conformational assignments can be refined. This introduces a general concept of modularity and secondary structure in oligosaccharides-essential for the success of similar studies on larger oligosaccharides in the future.

  DOI：

  10.1021/ja055891v
• 作为产物：
  描述：

  苯基 alpha-D-吡喃甘露糖苷 在 4 A molecular sieve 、 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -40.0~60.0 ℃ 、24.0 kPa 条件下， 反应 24.5h， 生成 phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-(1->3)-2-O-benzyl-4,6-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Building Up Key Segments of N-Glycans in the Gas Phase:  Intrinsic Structural Preferences of the α(1,3) and α(1,6) Dimannosides

  摘要：

  The intrinsic conformer specific vibrational spectra of two important subunits of the core pentasaccharide of Winked glycans, the alpha(1,3) and alpha(1,6) dimannosides, have been recorded in the gas phase. Coupling these measurements with a computational exploration of their conformational landscapes has enabled their conformational assignment and has identified characteristic vibrational signatures associated with particular conformational families-including those that do or do not display inter-ring hydrogen bonding across the glycosidic linkage. In addition, the IR spectra of the monosaccharide moieties provide benchmarks, through which the conformational assignments can be refined. This introduces a general concept of modularity and secondary structure in oligosaccharides-essential for the success of similar studies on larger oligosaccharides in the future.

  DOI：

  10.1021/ja055891v