5-O-allyl-1,2-O-isopropylidene-β-D-fructopyranose | 295791-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-allyl-1,2-O-isopropylidene-β-D-fructopyranose
• CAS: 295791-12-7
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: ZJXNMBKPEGJWMB-SVDPJWKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.21
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-O-allyl-1,2-O-isopropylidene-β-D-fructopyranose 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以93%的产率得到(2R,3S,4S,5R)-2-(hydroxymethyl)-5-prop-2-enoxyoxane-2,3,4-triol
  参考文献：
  名称：

  Synthesis and evaluation of fructose analogues as inhibitors of the d -fructose transporter GLUT5

  摘要：

  We have examined the specificity and binding-site spatial requirements of the fructose transporter GLUT5. Interaction with a series of fructofuranosides and fructopyranosides suggests that both furanose and pyranose ring forms of D-fructose combine with GLUT5. The epimers of D-fructose all have low affinity for GLUT5 suggesting that the transporter requires all hydroxyls to be in the fructo-configuration. Similarly there is poor tolerance of all allyl derivatives of D-fructose except 6-O-allyl-D-fructo-furanose. Therefore, the C-6 position offers the most suitable position for development of affinity probes and labels for exploring GLUT5 biochemistry. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00108-5
• 作为产物：
  描述：

  3-O-benzoyl-1,2-O-isopropylidene-β-D-fructopyranose 在 tris(dibenzylideneacetone)dipalladium (0) 吡啶 、 sodium methylate 、 三苯基膦 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 16.0h， 生成 5-O-allyl-1,2-O-isopropylidene-β-D-fructopyranose
  参考文献：
  名称：

  Synthesis and evaluation of fructose analogues as inhibitors of the d -fructose transporter GLUT5

  摘要：

  We have examined the specificity and binding-site spatial requirements of the fructose transporter GLUT5. Interaction with a series of fructofuranosides and fructopyranosides suggests that both furanose and pyranose ring forms of D-fructose combine with GLUT5. The epimers of D-fructose all have low affinity for GLUT5 suggesting that the transporter requires all hydroxyls to be in the fructo-configuration. Similarly there is poor tolerance of all allyl derivatives of D-fructose except 6-O-allyl-D-fructo-furanose. Therefore, the C-6 position offers the most suitable position for development of affinity probes and labels for exploring GLUT5 biochemistry. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00108-5