methyl 6-O-(diphenyl-(4-methoxyphenyl)-methyl)-α-D-fructofuranoside | 295791-14-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 6-O-(diphenyl-(4-methoxyphenyl)-methyl)-α-D-fructofuranoside
• CAS: 295791-14-9
• 化学式: C₂₇H₃₀O₇
• 分子量: 466.531
• InChiKey: OMXHIBLGYGOROI-XPGKHFPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.61
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 6-O-(diphenyl-(4-methoxyphenyl)-methyl)-α-D-fructofuranoside 在 吡啶 、 溶剂黄146 作用下， 反应 24.0h， 生成 methyl 1,3,4-tri-O-acetyl-α-D-fructofuranoside
  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：

  4-甲氧基三苯基氯甲烷 、 methyl α-D-fructofuranoside 在 吡啶 作用下， 以56%的产率得到methyl 6-O-(diphenyl-(4-methoxyphenyl)-methyl)-α-D-fructofuranoside
  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