1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside | 7143-89-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside
• 英文别名: 1,3,4,5-Tetra-O-benzoyl-β-D-fructopyranose；1,3,4,5-tetra-O-benzoylfructose；1,3,4,5-tetra-O-benzoyl-beta-D-fructopyranose；[(2R,3S,4R,5R)-3,4,5-tribenzoyloxy-2-hydroxyoxan-2-yl]methyl benzoate
• CAS: 7143-89-7
• 化学式: C₃₄H₂₈O₁₀
• 分子量: 596.59
• InChiKey: SCEVOPPMGXOQLM-DYKCOLQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  44
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside 在 tris(dibenzylideneacetone)dipalladium (0) 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 allyl β-D-fructopyranoside
  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：

  果糖 、 苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以89%的产率得到1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside
  参考文献：
  名称：

  [EN] RAPAMYCIN CARBOHYDRATE DERIVATIVES
  [FR] DERIVES DE RAPAMYCINE CARBOHYDRATE

  摘要：

  这项发明提供了经过改良的雷帕霉素，其具有通过连接剂连接的特定单糖，寡糖，伪糖或其衍生物，从而创造出具有增强药代动力学和/或药效动力学特性的雷帕霉素糖衍生物。例如，给予雷帕霉素糖衍生物的治疗导致了改变的药代动力学特性和降低的毒性。因此，本发明提供了具有与其他同类药物（如雷帕霉素）不同特性的化合物。

  公开号：

  WO2004101583A1

文献信息

• 一种果聚糖、其中间体、制备方法及用途
  申请人：上海医药工业研究院

  公开号：CN104231009B

  公开（公告）日：2017-07-04

  本发明公开了一种果聚糖、其中间体、制备方法及用途。该果聚糖I的制备方法包括：在有机溶剂中，在碱性试剂的作用下，将化合物II进行脱保护基反应，得到化合物I即可；其中，n=0～14，m=5～18；R3、R4、Rm为相同或者不相同的酰基。本发明的果聚糖具有较好的抗肿瘤活性，且其制备条件温和，产率较高。
• Rapamycin carbohydrate derivatives
  申请人：——

  公开号：US20040235762A1

  公开（公告）日：2004-11-25

  This invention provides modified rapamycins that have specific monosaccharide(s), oligosaccharide(s), pseudosugar(s) or derivatives thereof attached through a linker to create rapamycin carbohydrate derivatives having enhanced pharmacokinetic and/or pharmacodynamic profiles. For example, administration of the rapamycin carbohydrate derivative results in altered pharmacokinetic profiles and reduced toxicities. Thus, the present invention provides compounds with characteristics that are distinct from other drugs in its class such as rapamycin.

  这项发明提供了经过修改的雷帕霉素，其中通过连接剂连接了特定的单糖，寡糖，假糖或其衍生物，从而创建具有增强药代动力学和/或药效学特性的雷帕霉素糖衍生物。例如，给予雷帕霉素糖衍生物的治疗导致了改变的药代动力学特性和减少的毒性。因此，本发明提供了具有与其他类似药物（如雷帕霉素）不同特性的化合物。
• Synthesis of d-fructopyranosides with 2-O-acyl-β-d-fructopyranosides
  作者：Feng Lin、Qiulong Xu、Rui Lu、Liqun Yue

  DOI：10.1016/j.tetlet.2013.10.128

  日期：2014.1

  Glycosylation of 2-O-acyl fructopyranosides was investigated, which were shown to be effective glycosyl donors for D-fructopyranoside synthesis with good beta-selectivity and yields. For bulky acceptor 4e, alpha-anomer 5e was obtained with alpha/beta = 65:23. Unexpected ring-opening was observed during acetylation of 9, indicating the sensitivity of the fructopyranosyl ring. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of β-d-fructopyranosides with N-phenyl trifluoroacetimidate donor
  作者：Feng Lin、Gaoyan Lian、Qiulong Xu、Xiaofeng Zhu

  DOI：10.1016/j.tet.2012.11.058

  日期：2013.1

  Fructopyranosyl N-phenyl trifluoroacetimidate was demonstrated to be effective glycosyl donor for beta-D-fructopyranosides preparation that exhibited good beta-selectivity and good yields. X-ray data of two beta-D-fructopyranosides were obtained and help to determine the anomeric configuration of these ketoses. (C) 2012 Elsevier Ltd. All rights reserved.
• Lichtenthaler, Frieder W.; Klotz, Juergen; Flath, Franz-Josef, Liebigs Annalen, 1995, # 12, p. 2069 - 2080
  作者：Lichtenthaler, Frieder W.、Klotz, Juergen、Flath, Franz-Josef

  DOI：——

  日期：——