3,6-di-O-acetyl-5-(3-benzylthioureido)-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose | 1010809-31-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,6-di-O-acetyl-5-(3-benzylthioureido)-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose
• CAS: 1010809-31-0
• 化学式: C₂₁H₂₈N₂O₇S
• 分子量: 452.529
• InChiKey: FEQDXLJGODIZNT-ZWJWXYIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  104.35
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,6-di-O-acetyl-5-(3-benzylthioureido)-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose 在 mercury(II) oxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.75h， 以75%的产率得到3,6-di-O-acetyl-5-(N'-benzylcarbodiimido)-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Guanidine-Type Iminosugars

  摘要：

  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose -> piperidine rearrangement of 5-deoxy-5guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.

  DOI：

  10.1021/jo702374f
• 作为产物：
  描述：

  乙酸酐 、 5-(3-benzylthioureido)-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose 在 吡啶 作用下， 反应 2.0h， 以257 mg的产率得到3,6-di-O-acetyl-5-(3-benzylthioureido)-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Guanidine-Type Iminosugars

  摘要：

  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported. The synthetic strategy involves the furanose -> piperidine rearrangement of 5-deoxy-5guanidino-L-idose precursors. The reaction proceeds through elimination of water to give 3-oxopiperidines, which were isolated as the corresponding hydrates. Biological evaluation of the new glycomimetics evidenced a strong influence of the nature of the substituents at the nitrogen atoms on the glycosidase inhibitory properties.

  DOI：

  10.1021/jo702374f