1-[(1S)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl]-2-benzyl-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]guanidine;hydrochloride | 1010809-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(1S)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl]-2-benzyl-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]guanidine;hydrochloride
• CAS: 1010809-40-1
• 化学式: C₂₄H₃₇N₃O₁₀*ClH
• 分子量: 564.033
• InChiKey: PYRUQZYOBLOJEQ-SHDFPWOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  184
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-[(1S)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl]-2-benzyl-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]guanidine;hydrochloride 在 三氟乙酸 作用下， 以 水 为溶剂， 反应 0.5h， 生成 、
  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  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported.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：

  [(2S)-2-[(3aR,5R,6S,6aR)-6-acetyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[[N'-benzyl-N-[[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-methoxyoxan-2-yl]methyl]carbamimidoyl]amino]ethyl] acetate;hydrochloride 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-[(1S)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl]-2-benzyl-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methyl]guanidine;hydrochloride
  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  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported.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

文献信息

• Synthesis and Biological Evaluation of Guanidine-Type Iminosugars
  作者：Matilde Aguilar、Paula Díaz-Pérez、M. Isabel García-Moreno、Carmen Ortiz Mellet,* and、José M. García Fernández

  DOI：10.1021/jo702374f

  日期：2008.3.1

  [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.