(2S)-2-phenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetamide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S)-2-phenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetamide
• 化学式: C₂₀H₂₉NO₁₂
• 分子量: 475.45
• InChiKey: OCQMNDCGKQJTNY-YHVPUMHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  222
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S)-2-phenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetamide 在 吡啶 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以40 mg的产率得到neoamygdalin
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cyanogenic Glycosides

  摘要：

  An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.

  DOI：

  10.1080/07328303.2015.1105249
• 作为产物：
  描述：

  (S)-[6-O-(6-O-acetyl-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyloxy](phenyl)acetamide 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2S)-2-phenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cyanogenic Glycosides

  摘要：

  An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.

  DOI：

  10.1080/07328303.2015.1105249

文献信息

• Synthesis and Biological Evaluation of Cyanogenic Glycosides
  作者：Dmitry V. Yashunsky、Ekaterina V. Kulakovskaya、Tatiana V. Kulakovskaya、Olga S. Zhukova、Mikhail V. Kiselevskiy、Nikolay E. Nifantiev

  DOI：10.1080/07328303.2015.1105249

  日期：2015.10.13

  An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.