[(2S,3R,4S,5S,6R)-4-[[2-(benzenesulfonylimino)chromen-3-yl]methoxy]-5-hydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl] acetate | 1619921-34-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5S,6R)-4-[[2-(benzenesulfonylimino)chromen-3-yl]methoxy]-5-hydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl] acetate
• CAS: 1619921-34-4
• 化学式: C₂₅H₂₇NO₁₀S
• 分子量: 533.556
• InChiKey: WNAPUKMLSAUOIJ-JAWPICGBSA-N

物化性质

• 沸点：
  698.110±65.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.450±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.26
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  154.09
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-methoxy-4-((2-((phenylsulfonyl)imino)-2H-chromen-3-yl)methoxy)tetrahydro-2H-pyran-3,5-diyl diacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以56%的产率得到N-[3-[[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxymethyl]chromen-2-ylidene]benzenesulfonamide
  参考文献：
  名称：

  Synthesis and evaluation of iminocoumaryl and coumaryl derivatized glycosides as galectin antagonists

  摘要：

  A collection of iminocoumarylmethyl glycoside derivatives have been prepared by copper-catalyzed multi-component reaction of carbohydrate propargyl derivatives, sulfonyl azides, and salicylaldehyde or o-hydroxy acetophenone. The method is simple, versatile to all three components, and exceptionally high yielding. The carbohydrate N-sulfonyl iminocoumarine hybrid molecules were evaluated for binding galectin-1, -2, -3, -4 N, -4C, -7, -8 N, -9 N, and 9C using a competitive fluorescence polarization assay. Selective compounds were identified against galectin-3, 7, 8 N, and 9 N with up to 40-fold affinity enhancements relative to methyl alpha-D-galactopyranoside due to the coumarylmethyl moieties. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.063