((2R,3R,4S,5R,6R)-3-(((2R,3R,4R,5S,6R)-3-azido-5-(benzyloxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4,5-bis(benzyloxy)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy)tetrahydro-2H-pyran-2-yl)methyl hydrogen sulfate | 1383447-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2R,3R,4S,5R,6R)-3-(((2R,3R,4R,5S,6R)-3-azido-5-(benzyloxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4,5-bis(benzyloxy)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy)tetrahydro-2H-pyran-2-yl)methyl hydrogen sulfate
• CAS: 1383447-02-6
• 化学式: C₄₃H₅₀N₄O₁₅S
• 分子量: 894.954
• InChiKey: FBRKFIPNTMLOFM-XKDFRJCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.37
• 重原子数：
  63.0
• 可旋转键数：
  22.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  255.76
• 氢给体数：
  4.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  ((2R,3R,4S,5R,6R)-3-(((2R,3R,4R,5S,6R)-3-azido-5-(benzyloxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4,5-bis(benzyloxy)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy)tetrahydro-2H-pyran-2-yl)methyl hydrogen sulfate 在 1,3-丙二硫醇 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以93%的产率得到((2R,3R,4S,5R,6R)-3-(((2R,3R,4R,5S,6R)-3-amino-5-(benzyloxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4,5-bis(benzyloxy)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy)tetrahydro-2H-pyran-2-yl)methyl hydrogen sulfate
  参考文献：
  名称：

  Sulfoform generation from an orthogonally protected disaccharide

  摘要：

  An orthogonally protected disaccharide (GlcN(alpha 1 -> 4)Glc) with a beta-linked 2 '-aminoethyl linker was used to generate a series of sulfated derivatives (sulfoforms), with a 6-O-sulfate on the glucose residue and one or more sulfate esters on the terminal glucosamine. Deprotection and sulfonation steps were performed in solution and in variable order, with isolated yields of 36-54% (85-90% per operation) after HPLC purification. The modular deprotection-sulfonation sequences can be performed with efficient recovery of the polysulfate products, and avoids complications associated with heterogeneous reactivity in solid-phase synthesis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.04.010
• 作为产物：
  描述：

  ((2R,3R,4S,5R,6R)-3-(((2R,3R,4R,5S,6R)-3-azido-5-(benzyloxy)-6-(((tert-butyldiphenylsilyl)oxy)methyl)-4-hydroxytetrahydro-2H-pyran-2-yl)oxy)-4,5-bis(benzyloxy)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy)tetrahydro-2H-pyran-2-yl)methyl hydrogen sulfate 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以78%的产率得到((2R,3R,4S,5R,6R)-3-(((2R,3R,4R,5S,6R)-3-azido-5-(benzyloxy)-4-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4,5-bis(benzyloxy)-6-(2-(((benzyloxy)carbonyl)amino)ethoxy)tetrahydro-2H-pyran-2-yl)methyl hydrogen sulfate
  参考文献：
  名称：

  Sulfoform generation from an orthogonally protected disaccharide

  摘要：

  An orthogonally protected disaccharide (GlcN(alpha 1 -> 4)Glc) with a beta-linked 2 '-aminoethyl linker was used to generate a series of sulfated derivatives (sulfoforms), with a 6-O-sulfate on the glucose residue and one or more sulfate esters on the terminal glucosamine. Deprotection and sulfonation steps were performed in solution and in variable order, with isolated yields of 36-54% (85-90% per operation) after HPLC purification. The modular deprotection-sulfonation sequences can be performed with efficient recovery of the polysulfate products, and avoids complications associated with heterogeneous reactivity in solid-phase synthesis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.04.010