2,4-di-O-benzoyl-α-D-mannopyranosyl azide | 639464-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-di-O-benzoyl-α-D-mannopyranosyl azide
• 英文别名: 2,4-di-O-benzoyl-α-mannopyranosyl azide；[(2R,3S,4S,5S,6S)-6-azido-5-benzoyloxy-4-hydroxy-2-(hydroxymethyl)oxan-3-yl] benzoate
• CAS: 639464-28-1
• 化学式: C₂₀H₁₉N₃O₇
• 分子量: 413.387
• InChiKey: CNYJIGDOCOWXCS-WKULXVSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  117
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,4-di-O-benzoyl-α-D-mannopyranosyl azide 在 甲醇 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 生成 Bz(-2)[Bz(-4)]Man(a1-6)[Bz(-2)][Bz(-4)]Man(a)-N3
  参考文献：
  名称：

  Regioselective glycosylation of 3,6-unprotected mannoside derivatives: fast access to high-mannose type oligosaccharides

  摘要：

  A regioselective glycosylation of 3,6-unprotected mannoside acceptors was investigated. With glycosyl trichloroacetimidate donors, when an excess of trimethylsilyl trifluoromethanesulfonate is used as the catalyst, 6-O-glycosylation exclusively occurred affording a silylated disaccharide that could be involved in a subsequent glycosylation reaction. As an illustration, the fast synthesis of two trisaccharides and one pentasaccharide was achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.09.219
• 作为产物：
  描述：

  原苯甲酸三乙酯 在 camphor-10-sulfonic acid 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 2.17h， 生成 2,4-di-O-benzoyl-α-D-mannopyranosyl azide
  参考文献：
  名称：

  Synthesis and characterization of mannosyl mimetic derivatives based on a β-cyclodextrin core

  摘要：

  本研究介绍了在一个伯羟基上被甘露糖基拟态衍生物取代的支链δ-环糊精的合成。研究表明，目标化合物在水中的自包容现象并不排除环糊精分子的包容特性。

  DOI：

  10.1039/b301670f

文献信息

• Synthesis and characterization of mannosyl mimetic derivatives based on a β-cyclodextrin core
  作者：Duplex Yockot、Vincent Moreau、Gilles Demailly、Florence Djedaïni-Pilard

  DOI：10.1039/b301670f

  日期：——

  The synthesis of branched β-cyclodextrins substituted with mannosyl mimetic derivatives at one primary hydroxy group is described. It was shown that the self-inclusion phenomenon observed for the target compounds in water did not preclude the inclusion properties of the cyclodextrin moiety.

  本研究介绍了在一个伯羟基上被甘露糖基拟态衍生物取代的支链δ-环糊精的合成。研究表明，目标化合物在水中的自包容现象并不排除环糊精分子的包容特性。
• Regioselective glycosylation of 3,6-unprotected mannoside derivatives: fast access to high-mannose type oligosaccharides
  作者：Nicolas Smiljanic、Sami Halila、Vincent Moreau、Florence Djedaı̈ni-Pilard

  DOI：10.1016/j.tetlet.2003.09.219

  日期：2003.12.8

  A regioselective glycosylation of 3,6-unprotected mannoside acceptors was investigated. With glycosyl trichloroacetimidate donors, when an excess of trimethylsilyl trifluoromethanesulfonate is used as the catalyst, 6-O-glycosylation exclusively occurred affording a silylated disaccharide that could be involved in a subsequent glycosylation reaction. As an illustration, the fast synthesis of two trisaccharides and one pentasaccharide was achieved. (C) 2003 Elsevier Ltd. All rights reserved.