[(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 | 1010809-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: [(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
• CAS: 1010809-38-7
• 化学式: C₃₄H₄₇N₃O₁₅*ClH
• 分子量: 774.219
• InChiKey: KGLYPLBFVWBNQM-VFHKOPCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  53
• 可旋转键数：
  20
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  214
• 氢给体数：
  3
• 氢受体数：
  16

反应信息

• 作为反应物：
  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  [GRAPHICS]The preparation of carbohydrate mimics in which the endocyclic oxygen has been replaced by a guanidine-type nitrogen atom is reported.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
• 作为产物：
  描述：

  benzylamine hydrochloride 、 3,6-di-O-acetyl-5-deoxy-1,2-O-isopropylidene-5-[3-(methyl 2,3,4-tri-O-acetyl-6-deoxy-α-D-glucopyranosyd-6-yl)carbodiimido]-β-L-idofuranose 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以80%的产率得到[(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
  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